Roads Less Travelled podcast artwork

PODCAST · business

Roads Less Travelled

Passionate about real estate, rail trails, and the lifestyle they inspire? Join Craig Della Penna—Realtor and trail advocate—as he shares insights on buying homes near green corridors, bike tourism, and B&B opportunities. With decades of experience turning historic railroads into thriving assets, Craig offers inspiring stories, tips, and insider knowledge. Whether you’re a homebuyer, investor, or trail enthusiast, Roads Less Travelled releases new episodes every two weeks.

Publisher-supplied feed metadata · PodParley refreshed Jun 7, 2026 · Source feed

  1. 33

    Rail Trail Adventures & Cycling Tourism in New Hampshire with Marianne Borowski

    Marianne Borowski joins Craig Della Penna on Roads Less Travelled to discuss the creation and expansion of the 83-mile Cross New Hampshire Adventure Trail. Learn how historic rail corridors, multi-use collaborations, and local business partnerships are transforming rural tourism.🎧 Listen to the full episode of Roads Less Travelled now.🎙 What you'll learn:The layout and geography of the 83-mile Cross New Hampshire Adventure Trail.How combining rail trails with dirt back roads creates multi-day cycling journeys.The importance of community collaboration with local chambers and businesses.Managing multi-use trails alongside snowmobiles, ATVs, and walkers.Technical insights on trail surfacing, crushed stone mixes, and maintenance.Why cycle tourism drives sustainable economic growth in small mountain towns.🎧 HOSTED BY: Craig Della Penna👤 GUEST: Marianne Borowski – Trail Developer & Outdoor Recreation AdvocateMarianne Borowski is the President and Founder of the Cross New Hampshire Adventure Trail and Vice President of the New Hampshire Rail Trails Coalition. A former protein biochemist during the early years of biotech, she shifted careers after moving to Mt. Washington Valley in 2003, becoming a cross-country ski instructor, later director of the Jackson Ski Touring Foundation ski school, and now a member of its Board of Directors. Today, she focuses on restoring, maintaining, and connecting rail trails across New Hampshire. An avid cyclist, Marianne has also biked across the U.S.👉🏻 CONNECT WITH MARIANNE BOROWSKIFacebook: https://facebook.com/crossnewhampshire Instagram: https://instagram.com/crossnewhampshire 👉🏻 CONNECT WITH CRAIG DELLA PENNA – ROADS LESS TRAVELLEDWebsite: https://www.greenwaysolutions.org/Website: https://www.northamptonrealtor.com/Website: https://www.sugar-maple-inn.com/ Instagram: https://www.instagram.com/craigdp413/ LinkedIn: https://www.linkedin.com/in/craigdp/ 

  2. 32

    Sustainable Farming and Trail Access with Kristen Sykes

    Host Craig Della Penna welcomes conservationist and organic farmer Kristen Sykes to discuss the vital connections between local agriculture, trail infrastructure, and community well-being in Massachusetts.🎙 What you'll learn:How local trail networks and organic farms support community health and active transportation.The reality of managing an 8.5-acre organic farm on protected floodplain land.Why pedestrian infrastructure is essential for aging populations and car-free commuters.The intersection of local farm markets and small business support.How historical right-of-way conversions transformed travel routes in Massachusetts.The mental and physical health benefits of everyday access to nature.🎧 HOSTED BY: Craig Della Penna 👤 GUEST: Kristen Sykes – Conservationist, organic farmer, and advocate for sustainable land use and active mobility.Kristen Sykes is a conservationist, organic farmer, and advocate for biking and pedestrian infrastructure. She has been actively involved in advancing sustainable land use, active transportation, and community-based environmental initiatives. Through her work in conservation and agriculture, Kristen promotes healthier ecosystems and resilient local communities, while championing safe, accessible mobility options for all.💼 Connect with Steven Hawk:🌐 Website → https://www.facebook.com/kristen.sykes2/📷 Instagram → https://www.instagram.com/super.syked🔗 LinkedIn → https://www.linkedin.com/in/kristen-m-sykes/🎧 Follow Craig Della Penna:🌐 Website → https://www.greenwaysolutions.org/🌐 Website → https://www.northamptonrealtor.com/🌐 Website →https://www.sugar-maple-inn.com/📷 Instagram → https://www.instagram.com/craigdp413/🔗 LinkedIn → https://www.linkedin.com/in/craigdp/⭐ Produced by Icons of Real Estate - https://iconsofrealestate.com/Don’t forget to LIKE 👍 SUBSCRIBE 🔔 COMMENT 💬 below! 

  3. 31

    How One Advocate is Transforming Rail Trails for Wheelchair Access

    How one resident transformed a muddy path into an accessible community lifeline.Steven Hawk joins Craig to explore the powerful impact of ADA-compliant rail trails in small towns like Ware, Massachusetts. Steven shares how he advocated for safer access points, leading to rapid infrastructure improvements that benefit everyone from wheelchair users to local dog walkers. This episode covers practical strategies for communicating with town officials, the economic potential of accessible outdoor spaces, and the future of integrating local history into community paths.🎧 Hosted by: Craig🎤 Featuring: Steven HawkSteven Hawk is a resident of Ware, Massachusetts, and an active user of the local Rail Trail. As a wheelchair user, Steven relies on the trail several times a week for transportation, grocery shopping, visiting family and friends, and enjoying time outdoors. His experience highlights the importance of accessible community spaces that support independence, connection, and mobility for people of all abilities.💡 What You’ll Learn in This Episode:✔ Transforming personal physical limitations into community-wide accessibility improvements✔ Educating local officials on the real-world impact of ADA compliance✔ Building productive relationships with town managers to fix safety hazards✔ Utilizing the third place concept to revitalize small-town economies✔ Securing fast infrastructure updates by speaking directly to land developers✔ Implementing QR codes to share local history and community wayfinding resources✔ Encouraging outdoor exploration and independence for residents of all abilities💼 Connect with Steven Hawk:🌐 Email → [email protected]🎧 Follow Craig Della Penna:🌐 Website → https://www.greenwaysolutions.org/🌐 Website → https://www.northamptonrealtor.com/🌐 Website →https://www.sugar-maple-inn.com/📷 Instagram → https://www.instagram.com/craigdp413/🔗 LinkedIn → https://www.linkedin.com/in/craigdp/⭐ Produced by Icons of Real Estate - https://iconsofrealestate.com/🔖 Don’t Forget to LIKE 👍, SUBSCRIBE 🔔 & COMMENT 💬 Below!#RailTrail #Accessibility #ADACompliance #CommunityDevelopment #OutdoorRecreation #InclusiveDesign #SmallTowns #WheelchairAccess

  4. 30

    E-Bikes, Rail Trails, and Community Revitalization with David

    Explore how Western Massachusetts is balancing modern transit shifts, trail safety, and community engagement with former eMarketer analyst David.Joined by host Craig, David shares insights from his transition to Northampton, discussing everything from e-bike regulations on local trails to creative solutions for vacant downtown landmarks.🎧 Hosted by: Craig      🎤 Featuring: DavidDavid is a retired communications professional, former chief marketing officer, and community volunteer in Western Massachusetts with a background in digital media trends and local advocacy.💡 What You’ll Learn in This Episode:✔️ The impact of class-three e-bikes on traditional walking and biking trails✔️ The history of regional rail corridors and future trail expansions✔️ Policy tools to revitalize vacant community spaces like the Calvin Theater✔️ The importance of screen-free environments for building local connection✔️ Unique grassroots sustainability projects like pedal-powered waste management📇 Connect with David:🌐 David’s journey → https://sl1nk.com/olxzwuh🔗 LinkedIn → https://www.linkedin.com/in/hallerman/📇 Connect with Craig:🌐 Website → https://www.greenwaysolutions.org/🌐 Website → https://www.northamptonrealtor.com/🌐 Website →https://www.sugar-maple-inn.com/📘 Facebook →📷 Instagram → https://www.instagram.com/craigdp413/🔗 LinkedIn → https://www.linkedin.com/in/craigdp/⭐ Produced by Icons of Real Estate - https://iconsofrealestate.com/🔖 Don’t Forget to LIKE 👍, SUBSCRIBE 🔔 & COMMENT 💬 Below!

  5. 29

    How Social Entrepreneurship Is Changing Local Business Forever

     🚀 In this episode, host Craig Della Pena sits down with Tara Brewster, VP of Business Development at Greenfield Savings Bank, to explore the power of community banking, social entrepreneurship, and kindness in local development. Tara shares her journey from entrepreneur to banker, her passion for giving back, and her vision for Western Massachusetts’ future. From partnerships between nonprofits and businesses, to the impact of kindness and collaboration, this episode shines a light on building stronger communities together.🎧 Hosted by: Craig Della Pena👤 Guest:Tara Brewster – VP of Business Development, Greenfield Savings Bank & Community LeaderTara Brewster is the Vice President of Business Development and Director of Philanthropy at Greenfield Savings Bank, where she leverages her entrepreneurial experience and strong community ties to foster partnerships and philanthropic initiatives across Western Massachusetts. A respected community leader, she’s been honored as a BusinessWest 40 Under Forty alum and recognized as a Difference Maker in 2022 for her tireless work raising funds and awareness for area nonprofits. In addition, she was recently appointed as a trustee for the Community Foundation of Western Massachusetts, reinforcing her influence in helping drive equity and opportunity in the region.💡 What You’ll Learn: ✔️ The difference between community mutual banks and “too big to fail” stock banks ✔️ How social entrepreneurship drives innovation and community impact ✔️ Real-world examples of nonprofits and businesses partnering for change ✔️ The importance of kindness, relationships, and helping others ✔️ Why Western Massachusetts is a unique and thriving place to live ✔️ Tara’s vision for the region’s growth and collaboration in the next decade🎵 Whether you’re a business owner, nonprofit leader, or simply passionate about community, this episode will inspire you to see how kindness and collaboration can transform local life.💼 Connect with Tara Brewster:🌐 Website → https://www.greenfieldsavings.com/💼 LinkedIn → https://www.linkedin.com/in/taratbrewster/🎧 Follow Craig Della Pena:🌐 Website → https://www.greenwaysolutions.org/🌐 Website → https://www.northamptonrealtor.com/🌐 Website →https://www.sugar-maple-inn.com/📘 Facebook →📷 Instagram → https://www.instagram.com/craigdp413/🔗 LinkedIn → https://www.linkedin.com/in/craigdp/⭐ Produced by Icons of Real Estate - https://iconsofrealestate.com/

  6. 28

    How the Empire State Trail Created a $1.87B Economy

    In this episode, Craig sits down with Dylan Carey, Director of Policy & Planning at Parks & Trails New York, to discuss the newly released economic impact report showing the trail network generates $1.87 billion annually for New York's economy.From boosting local businesses and increasing property values to creating healthier communities and expanding tourism, Dylan explains why trails are far more than recreational amenities—they're powerful economic development tools. The conversation also explores trail-oriented development, bike-friendly communities, and the future vision for expanding interconnected greenway systems across New York and beyond.🎧 Hosted by: Craig Della Penna 👤 Guest:Dylan Carey – Director of Policy & Planning, Parks & Trails New YorkDylan Carey is the Director of Policy and Planning for Parks & Trails New York, leading advocacy efforts to expand the state's greenway networks and support public lands. Leveraging a background in politics and government, he collaborates with local communities to maximize the economic impact of these resources and promote the Empire State Trail. 💡 What You'll Learn:✔️ How the Empire State Trail generates $1.87 billion in annual economic impact✔️ Why trails increase tourism, local business revenue, and property values✔️ The role of trail-oriented development in community revitalization✔️ What makes a bike-friendly business or bed & breakfast successful✔️ The future vision for expanding New York's statewide trail network🎵 Whether you're an investor, agent, or homebuyer, this episode offers valuable insights!💼 Connect with Dylan Carey:🌐 Website → https://www.ptny.org/📸 Instagram → https://www.instagram.com/parkstrailsny/👻 Facebook → https://www.facebook.com/parksandtrailsny🔗 LinkedIn → https://www.linkedin.com/in/dylan-carey-08611a76/🔗 LinkedIn → https://www.linkedin.com/company/parks-&-trails-new-york/🎧 Follow Craig Della Penna:🌐 Website → https://www.greenwaysolutions.org/🌐 Website → https://www.northamptonrealtor.com/🌐 Website →https://www.sugar-maple-inn.com/📷 Instagram → https://www.instagram.com/craigdp413/🔗 LinkedIn → https://www.linkedin.com/in/craigdp/📌 Don’t Forget to LIKE 👍, SUBSCRIBE 🔔 & COMMENT 💬 Below! ⭐ Produced by Icons of Real Estate - https://iconsofrealestate.com/

  7. 27

    How Cities Can Fix Housing Using “Tax Per Acre” Thinking

     🚀 In this conversation, developer and former touring musician Scott Graves joins host Craig Della Penna to explore how jazz improvisation, economic theory, and urban planning intersect. From Vermont to Massachusetts, Scott explains how housing policy, zoning, and infrastructure design shape the health of communities—and why America’s built environment may be undermining both economic opportunity and social connection.🎧 Hosted by: Craig Della Penna👤 Guest: 🏡 Scott Graves – Principal, SMG Graves Associates | Construction Project Manager | Mixed-Use Housing Developer | Economic Development Strategist💡 What You’ll Learn: ✔️ How jazz improvisation mirrors real estate development and urban planning ✔️ Why zoning and housing policy shape community health and economic resilience ✔️ The hidden cost of suburban sprawl and underused urban land ✔️ Why “tax revenue per acre” matters more than expansion-based growth models ✔️ How cities can unlock housing by activating vacant lots and reforming land use🎵 Whether you're an investor, agent, or homebuyer, this episode offers valuable insights!💼 Connect with Scott Graves:🌐 Website → http://smgravesassociates.com/📸 Instagram → https://www.instagram.com/arewehereyetpodcast/🎧 Follow Craig Della Penna:🌐 Website → https://www.greenwaysolutions.org/🌐 Website → https://www.northamptonrealtor.com/🌐 Website →https://www.sugar-maple-inn.com/📷 Instagram → https://www.instagram.com/craigdp413/🔗 LinkedIn → https://www.linkedin.com/in/craigdp/📌 Don’t Forget to LIKE 👍, SUBSCRIBE 🔔 & COMMENT 💬 Below! ⭐ Produced by Icons of Real Estate - https://iconsofrealestate.com/

  8. 26

    How Mixed-Use Housing Can Revive Small Towns

    🚀 In this episode, Craig Della Penna sits down with Scott Graves to explore how affordable housing, entrepreneurial ecosystems, and connected transportation networks can transform communities. Drawing on decades of experience in construction, mixed-use development, and economic research, Scott explains why housing and job creation must go hand in hand. He also shares how rail trails, walkable downtowns, and locally driven investment strategies are helping revitalize small cities and rural communities across New England.🎧 Hosted by: Craig Della Penna👤 Guest:🏡 Scott Graves – Principal, SMG Graves Associates | Construction Project Manager | Mixed-Use Housing Developer | Economic Development Strategist💡 What You'll Learn:✔️ Why affordable housing and quality job creation must be developed together✔️ How mixed-use downtown developments benefit both young professionals and empty nesters✔️ The economic value of rail trails, walkable communities, and connected neighborhoods✔️ Why locally driven investment and entrepreneurship outperform grant dependency✔️ Practical strategies for creating resilient small-town economies🎵 Whether you're an investor, developer, planner, entrepreneur, or community leader, this episode offers valuable insights!💼 Connect with Scott Graves:🌐 Website → http://smgravesassociates.com/📸 Instagram → https://www.instagram.com/arewehereyetpodcast/🎧 Follow Craig Della Penna:🌐 Website → https://www.greenwaysolutions.org/🌐 Website → https://www.northamptonrealtor.com/🌐 Website →https://www.sugar-maple-inn.com/📷 Instagram → https://www.instagram.com/craigdp413/🔗 LinkedIn → https://www.linkedin.com/in/craigdp/📌 Don’t Forget to LIKE 👍, SUBSCRIBE 🔔 & COMMENT 💬 Below! ⭐ Produced by Icons of Real Estate - https://iconsofrealestate.com/

  9. 25

    Why Most Adults Quit Cycling Too Soon

    🚀 In this inspiring episode, host Craig Della Penna sits down with longtime cycling advocate and rail trail enthusiast Elizabeth Johnson to discuss how rail trails can transform lives, communities, and local economies. Elizabeth shares her personal journey from rediscovering cycling through the Norwottuck Rail Trail to becoming a passionate advocate for trail networks throughout Massachusetts and New England. The conversation explores adaptive cycling solutions, trail towns, community building, public health benefits, and how trail-oriented development is shaping the future of real estate and transportation.🎧 Hosted by: Craig Della Penna👤 Guest:🏡 Elizabeth Johnson – Retired Educator, Cycling Advocate & Rail Trail AdvocateElizabeth Johnson is an adult cycling advocate who discovered her passion for riding on the Norwottuck and Mass Central Rail Trails. She actively promote adult cycling, sharing her journey to show that biking is a fun and healthy way to enjoy life.💡 What You’ll Learn:✔️ How Elizabeth rediscovered her passion for cycling through the Norwottuck Rail Trail✔️ The physical and mental health benefits of rail trail access✔️ How adaptive bike modifications can make cycling accessible at any age✔️ Why trail towns create economic opportunities and community growth✔️ How trail-oriented development is influencing the future of real estate🎵 Whether you're an investor, planner, cyclist, community leader, or outdoor enthusiast, this episode offers valuable insights!💼 Connect with Elizabeth Johnson:🌐 Website → https://www.youtube.com/@RideandShineBicycling📸 Instagram → https://www.instagram.com/rideandshinebicycling/🎧 Follow Craig Della Penna:🌐 Website → https://www.greenwaysolutions.org/🌐 Website → https://www.northamptonrealtor.com/🌐 Website →https://www.sugar-maple-inn.com/📷 Instagram → https://www.instagram.com/craigdp413/🔗 LinkedIn → https://www.linkedin.com/in/craigdp/📌 Don’t Forget to LIKE 👍, SUBSCRIBE 🔔 & COMMENT 💬 Below! ⭐ Produced by Icons of Real Estate - https://iconsofrealestate.com/

  10. 24

    How a Forgotten Railroad Revived an Entire Small Town

    🚀 In this episode, conservationist Michael Calhoun shares the remarkable story behind Oregon’s first rail-trail conversion, the Banks-Vernonia Trail. Michael discusses how abandoned railroad corridors became valuable community assets, the process of earning National Recreation Trail certification, balancing conservation with recreation, and the economic and cultural benefits trails bring to small towns. He also explores trail tourism, forestry, environmental stewardship, and the future of Oregon’s trail networks.🎧 Hosted by: Craig Della Penna👤 Guest:🏡 Michael Calhoun – Conservationist, Trail Advocate, and Board Chair of the Columbia Soil and Water Conservation District💡 What You’ll Learn:✔️ The history behind Oregon’s first rail-trail conversion✔️ How National Recreation Trail certification works✔️ The economic impact of trail tourism on rural communities✔️ Balancing recreation with environmental conservation✔️ Strategies for preserving railroad heritage and local history✔️ The importance of urban forestry and dark-sky initiatives✔️ Advice for grassroots advocates working to save historic rail corridors🎵 Whether you're a trail enthusiast, conservation advocate, community leader, or history buff, this episode offers valuable insights into preserving the past while building a sustainable future.💼 Connect with Michael Calhoun:🌐 Website → https://shorturl.at/E8yBJ🔗 LinkedIn → https://www.linkedin.com/in/michael--calhoun🎧 Follow Craig Della Penna:🌐 Website → https://www.greenwaysolutions.org/🌐 Website → https://www.northamptonrealtor.com/🌐 Website →https://www.sugar-maple-inn.com/📷 Instagram → https://www.instagram.com/craigdp413/🔗 LinkedIn → https://www.linkedin.com/in/craigdp/📌 Don’t Forget to LIKE 👍, SUBSCRIBE 🔔 & COMMENT 💬 Below! ⭐ Produced by Icons of Real Estate - https://iconsofrealestate.com/

  11. 23

    How Massachusetts Is Building Trails Faster Than Ever

    🚀 In this episode, Craig Della Penna sits down with Amanda Lewis, Director of MassTrails at the Massachusetts Department of Conservation and Recreation (DCR), to explore the vision, growth, and future of trails across the Commonwealth. Amanda shares how MassTrails is connecting communities through a statewide network of recreational trails and shared-use paths, the impact of the MassTrails Grant Program, innovations in trail mapping and accessibility, the launch of MassTrails10, and what lies ahead for trail development in Massachusetts. Whether you're a trail advocate, planner, municipal leader, or outdoor enthusiast, this conversation offers valuable insights into the power of trails to transform communities.🎧 Hosted by: Craig Della Penna👤 Guest:🏡 Amanda Lewis – Director of MassTrails, Massachusetts Department of Conservation and Recreation (DCR)💡 What You’ll Learn:✔️ The vision behind MassTrails and how agencies collaborate statewide✔️ How the MassTrails Grant Program has funded over 500 trail projects✔️ The role of GIS, digital mapping, and trail data in improving public access✔️ Why accessibility and equity are central to modern trail planning✔️ How MassTrails10 is promoting trail tourism and outdoor recreation across Massachusetts🎵 Whether you're a planner, trail advocate, municipal leader, cyclist, hiker, investor, or outdoor enthusiast, this episode offers valuable insights into the future of trails and recreation in Massachusetts!💼 Connect with Amanda Lewis:🔗 LinkedIn → https://www.linkedin.com/in/amanda-krchak-lewis-b250662a/🎧 Follow Craig Della Penna:🌐 Website → https://www.greenwaysolutions.org/🌐 Website → https://www.northamptonrealtor.com/🌐 Website →https://www.sugar-maple-inn.com/📷 Instagram → https://www.instagram.com/craigdp413/🔗 LinkedIn → https://www.linkedin.com/in/craigdp/📌 Don’t Forget to LIKE 👍, SUBSCRIBE 🔔 & COMMENT 💬 Below! ⭐ Produced by Icons of Real Estate - https://iconsofrealestate.com/

  12. 22

    How Massachusetts Could Save Its State Parks Before It’s Too Late

    🚀 In this insightful episode, Doug Pizzi, Executive Director of Mass Parks for All, joins Craig Della Penna to discuss the history, funding, and future of Massachusetts state parks. From the origins of America’s first public parks to today’s challenges surrounding conservation funding, Doug shares how public lands impact environmental protection, recreation, public health, and economic growth. The discussion also explores the Mass Central Rail Trail, DCR funding priorities, and why investing in parks is critical for future generations.🎧 Hosted by: Craig Della Penna👤 Guest:🏡 Doug Pizzi – Executive Director, Mass Parks for AllDoug Pizzi is the Executive Director of Mass Parks for All, a nonprofit organization advocating for the protection and modernization of public lands. He previously served as Executive Director of Massachusetts Conservation Voters and brings extensive experience in environmental policy, communications, and nonprofit advocacy, including work with organizations such as Friends of the Earth and the National Wildlife Federation.💡 What You’ll Learn:✔️ The history of Massachusetts state parks and conservation✔️ Why public parks are essential for mental and physical wellbeing✔️ How Mass Parks for All advocates for better park investment✔️ The economic and environmental impact of rail trails and outdoor recreation✔️ How communities can help protect and improve public lands✔️ The future outlook for conservation and state park funding in Massachusetts🎵 Whether you're an investor, advocate, outdoor enthusiast, or community leader, this episode offers valuable insights!💼 Connect with Doug Pizzi: 🌐 Website → https://www.massparksforall.org/📷 Instagram → https://www.instagram.com/dougpizzi/🔗 LinkedIn → https://www.linkedin.com/in/pizzicommunications/🎧 Follow Craig Della Penna:🌐 Website → https://www.greenwaysolutions.org/🌐 Website → https://www.northamptonrealtor.com/🌐 Website →https://www.sugar-maple-inn.com/📷 Instagram → https://www.instagram.com/craigdp413/🔗 LinkedIn → https://www.linkedin.com/in/craigdp/📌 Don’t Forget to LIKE 👍, SUBSCRIBE 🔔 & COMMENT 💬 Below! ⭐ Produced by Icons of Real Estate - https://iconsofrealestate.com/

  13. 21

    How to Protect Your Mental Health During a Move

    🚀 In this episode, Craig Della Penna sits down with Beth Agostino-Evans, a licensed independent clinical social worker with more than 20 years of experience in behavioral health and trauma-informed care. Beth shares her expertise on mental health, emotional resilience, mindfulness, and how outdoor spaces and community wellness initiatives positively impact emotional wellbeing.The conversation also explores the emotional stress tied to buying and selling homes, how repeated relocations affect families, and why having trusted support systems during major life changes is so important. From evidence-based therapy approaches to the long-term impacts of chronic stress, this episode offers practical guidance for anyone navigating transitions, anxiety, or personal growth.🎧 Hosted by: Craig Della Penna👤 Guest:🏡 Beth Agostino-Evans – Licensed Independent Clinical Social WorkerBeth Agostino-Evans, MSW, LICSW is a clinical social worker with more than 20 years of experience specializing in focused, evidence-based treatment. She serves as the Director of Clinical Services at a mental health agency in the Pioneer Valley. A graduate of Assumption College and Boston University’s Master of Social Work program, Beth brings deep expertise in trauma-informed care, behavioral health, and community-based mental health services.💡 What You’ll Learn:✔️ How outdoor spaces and nature support emotional wellness✔️ Why buying or selling a home creates emotional stress✔️ Evidence-based therapy approaches that help clients thrive✔️ The mental health impact of repeated relocations and life transitions✔️ Practical mindfulness and self-care strategies during stressful times✔️ Common misconceptions about therapy and mental health support✔️ How COVID changed the mental health profession and therapy delivery🎵 Whether you're an investor, agent, homeowner, or someone navigating life transitions, this episode offers meaningful mental health insights and practical wellness strategies!💼 Connect with Beth Agostino-Evans:🌐 Website → https://www.psychologytoday.com/profile/1380412🎧 Follow Craig Della Penna:🌐 Website → https://www.greenwaysolutions.org/🌐 Website → https://www.northamptonrealtor.com/🌐 Website →https://www.sugar-maple-inn.com/📷 Instagram → https://www.instagram.com/craigdp413/🔗 LinkedIn → https://www.linkedin.com/in/craigdp/📌 Don’t Forget to LIKE 👍, SUBSCRIBE 🔔 & COMMENT 💬 Below! ⭐ Produced by Icons of Real Estate - https://iconsofrealestate.com/

  14. 20

    Why Cities Fail at Urban Revitalization Projects

    🚀 In this inspiring episode, Craig Della Penna sits down with Peter Stanton and Walter Henritze, co-founders of the Union Station Alliance, to discuss the extraordinary grassroots effort that helped save and restore Worcester’s historic Union Station. From abandoned ruins and political resistance to civic pride and urban revival, this conversation explores how passion, persistence, and community activism transformed one of Massachusetts’ most iconic transportation landmarks into a symbol of Worcester’s rebirth.🎧 Hosted by: Craig Della Penna👤 Guests:🏡 Peter Stanton – Former Publisher of Worcester Business Journal🏡 Walter Henritze – Entrepreneur & Civic AdvocatePeter Stanton and Walter Henritze are co-founders of the Union Station Alliance, the group that helped drive the successful restoration of Worcester’s historic Union Station. Peter recently retired after 40 years as Publisher of the Worcester Business Journal, while Walter is a serial entrepreneur who has led startups across media, technology, and nonprofit arts. Together, they offer firsthand perspective on the station’s revival and its impact today.💡 What You’ll Learn:✔️ How a small grassroots group helped save Worcester’s Union Station✔️ The emotional connection communities have to historic train stations✔️ Why persistence and “showing up” matters in civic activism✔️ The role historic preservation plays in urban revitalization✔️ How Union Station became a symbol of Worcester’s momentum and rebirth🎵 Whether you're an investor, urban planner, preservationist, or community advocate, this episode offers valuable insights!💼 Connect with Peter Stanton:🌐 Website → https://www.wbjournal.com/staff/Peter-Stanton🔗 LinkedIn → linkedin.com/in/peter-stanton-02a34a17💼 Connect with Walter Henritze:🔗 LinkedIn → https://www.linkedin.com/in/whenritze🎧 Follow Craig Della Penna:🌐 Website → https://www.greenwaysolutions.org/🌐 Website → https://www.northamptonrealtor.com/🌐 Website →https://www.sugar-maple-inn.com/📷 Instagram → https://www.instagram.com/craigdp413/🔗 LinkedIn → https://www.linkedin.com/in/craigdp/📌 Don’t Forget to LIKE 👍, SUBSCRIBE 🔔 & COMMENT 💬 Below! ⭐ Produced by Icons of Real Estate - https://iconsofrealestate.com/

  15. 19

    How Connected Bike Trails Become Economic Engines

    🚀 In this insightful conversation, host Craig Della Penna interviews Dan Hodge and Ann Ormsbee about the newly completed economic impact study for the New Haven and Northampton Canal Greenway.The discussion explores how shared-use trails generate economic activity, attract tourism, support local businesses, and influence policymakers to invest in long-distance trail infrastructure. Dan and Ann explain the mechanics behind economic impact studies, including direct, indirect, and induced spending, while also discussing trail connectivity, transportation synergies, and the broader vision for interconnected interstate trail systems across New England.🎧 Hosted by: Craig Della Penna👤 Guests:🏡 Dan Hodge – Economic Development & Transportation Planning Expert🏡 Ann Ormsbee – Economic Impact & Community Development SpecialistDan Hodge, Executive Vice President at Cambridge Econometrics, brings 25+ years of experience in economic development, transportation planning, and economic impact analysis, backed by prior roles at the UMass Donahue Institute, HDR, and Cambridge Systematics. Ann Ormsbee, Senior Economist at Cambridge Econometrics, specializes in economic development strategy and fiscal and economic impact studies, including major shared-use path projects. Together, they lead analyses that shape transportation and community planning across the U.S.💡 What You’ll Learn:✔️ How rail trails generate economic impact and tourism spending✔️ Why completing trail gaps dramatically increases economic potential✔️ How policymakers use economic impact studies to justify trail investments✔️ Why connected interstate trail systems matter for regional development✔️ The role of Amtrak and multimodal transportation in trail tourism✔️ Why recreational use statutes impact trail expansion projects🎵 Whether you're an investor, planner, policymaker, trail advocate, or community leader, this episode offers valuable insights!💼 Connect with Dan Hodge & Ann Ormsbee: 🌐 Website → https://www.camecon.com/ 🔗 LinkedIn → https://www.linkedin.com/in/danhodge-econ/ 🔗 LinkedIn → https://www.linkedin.com/in/annormsbee/ 🎧 Follow Craig Della Penna:🌐 Website → https://www.greenwaysolutions.org/🌐 Website → https://www.northamptonrealtor.com/🌐 Website →https://www.sugar-maple-inn.com/📷 Instagram → https://www.instagram.com/craigdp413/🔗 LinkedIn → https://www.linkedin.com/in/craigdp/📌 Don’t Forget to LIKE 👍, SUBSCRIBE 🔔 & COMMENT 💬 Below! ⭐ Produced by Icons of Real Estate - https://iconsofrealestate.com/

  16. 18

    The Biggest Mistake New B&B Owners Make

    🚀 In this episode, we sit down with Jenelle Cruz, owner of a stunning historic vegan bed & breakfast in Northeastern Washington. From leaving a 15-year career as a registered dietitian to restoring a former convent built in 1873, Jenelle shares her journey into hospitality, sustainable living, and creating a destination experience rooted in nature, history, and plant-based living.🎧 Hosted by: Craig Della Penna👤 Guest:🏡 Jenelle Cruz – Innkeeper & Former Registered DietitianJenelle Cruz is the owner and operator of Gardenview Estate Bed & Breakfast, a historic vegan inn in northeastern Washington State. Built in 1873, the estate has served as Saint Francis Regis Mission, Sacred Heart Academy, and Lady of the Valley Convent. Jenelle, a former registered dietitian, restored the property and now welcomes guests seeking nature, history, and plant-based living near the Great American Rail Trail and Pend Oreille Wildlife Refuge.💡 What You’ll Learn:✔️ How Jenelle transitioned from healthcare to hospitality✔️ The history behind a former convent turned B&B✔️ Creating a vegan guest experience (even for non-vegans!)✔️ Marketing and managing a rural destination property✔️ The realities of running a B&B solo🎵 Whether you're an investor, agent, or homebuyer, this episode offers valuable insights!💼 Connect with Jenelle Cruz:🌐 Website → https://www.gardenviewestatebnb.com/🌐 Website → https://www.wanderwithwonder.com/gardenview-estate-vegan-inn-washington-boutique-inn/ 🎧 Follow Craig Della Penna:🌐 Website → https://www.greenwaysolutions.org/🌐 Website → https://www.northamptonrealtor.com/🌐 Website →https://www.sugar-maple-inn.com/📷 Instagram → https://www.instagram.com/craigdp413/🔗 LinkedIn → https://www.linkedin.com/in/craigdp/📌 Don’t Forget to LIKE 👍, SUBSCRIBE 🔔 & COMMENT 💬 Below! ⭐ Produced by Icons of Real Estate - https://iconsofrealestate.com/

  17. 17

    What No One Tells You About Bike Tourism

    🚀 In this episode, Craig Della Penna sits down with Glenn Pransky, President of the Mass Central Rail Trail Alliance, to explore the transformative power of rail trails. From Glenn’s early cycling adventures to his leadership in developing a 100-mile trail across Massachusetts, this conversation dives into how bike tourism revitalizes communities, boosts local economies, and improves public health. Learn what it takes to plan a successful cycling trip, overcome opposition to trail development, and why long-distance rail trails are shaping the future of travel and recreation.🎧 Hosted by: Craig Della Penna👤 Guest:🏡 Glenn Pransky – President, Mass Central Rail Trail AllianceCraig Della Penna is a pioneering Realtor and nationally recognized rail-trail advocate, and the host of Roads Less Travelled. As the first U.S. Realtor to specialize exclusively in properties along scenic rail-trail corridors, Craig blends his expertise in real estate with decades of experience transforming “dead” railroads into thriving community assets. A former New England organizer for the Rails-to-Trails Conservancy, he has delivered over 1,200 lectures in 21 states, authored five books, and was hailed by Ride Magazine as the most effective rail-to-trail advocate on the Eastern Seaboard.💡 What You’ll Learn:✔️ How rail trails transform local economies and communities✔️ Essential tips for planning a stress-free bike touring trip✔️ The history and growth of bike tourism in the U.S.✔️ Common challenges in trail development—and how to overcome them✔️ The public health and environmental benefits of cycling infrastructure🎵 Whether you're an investor, agent, or homebuyer, this episode offers valuable insights!💼 Connect with Glenn Pransky:🌐 Email → [email protected]🎧 Follow Craig Della Penna:🌐 Website → https://www.greenwaysolutions.org/🌐 Website → https://www.northamptonrealtor.com/🌐 Website →https://www.sugar-maple-inn.com/📷 Instagram → https://www.instagram.com/craigdp413/🔗 LinkedIn → https://www.linkedin.com/in/craigdp/📌 Don’t Forget to LIKE 👍, SUBSCRIBE 🔔 & COMMENT 💬 Below! ⭐ Produced by Icons of Real Estate - https://iconsofrealestate.com/

  18. 16

    The Biggest Mistake Killing Trail Development Projects

    🚀 In this episode, we sit down with Mike Kowalczyk to explore how grassroots efforts are transforming abandoned rail corridors into thriving trail networks across New Hampshire and beyond. From overcoming community resistance to building cross-state partnerships, Mike shares how small wins, collaboration, and persistence are turning vision into reality—connecting towns, boosting tourism, and preserving history along the way.🎧 Hosted by: Craig Della Penna👤 Guest:🏡 Mike Kowalczyk – Rail Trail Advocate & Project LeaderMike Kowalczyk is the founder and president of the Monadnock Region Rail Trail Collaborative, leading efforts to rehabilitate and connect nearly 100 miles of rail trails across southwest New Hampshire and into Massachusetts and Vermont. Since retiring from a career in project management in 2017, Mike has become a key advocate for trail development, serving as chair of the Swanzey Rail Trail Advisory Committee, board member of the New Hampshire Rail Trail Coalition, and member of the Rails-to-Trails Conservancy.💡 What You’ll Learn:✔️ How to turn community resistance into support✔️ The “remove the excuses” mindset for progress✔️ How small trail projects lead to big regional impact✔️ The importance of cross-state collaboration in trail networks✔️ How rail trails boost tourism, community, and local economies🎵 Whether you're an investor, agent, or homebuyer, this episode offers valuable insights!💼 Connect with Mike Kowalczyk:🌐 Website → https://monadnockrailtrails.org/📘 Facebook → https://www.facebook.com/p/Monadnock-Region-Rail-Trail-Collaborative-100083745592629/🎧 Follow Craig Della Penna:🌐 Website → https://www.greenwaysolutions.org/🌐 Website → https://www.northamptonrealtor.com/🌐 Website →https://www.sugar-maple-inn.com/📷 Instagram → https://www.instagram.com/craigdp413/🔗 LinkedIn → https://www.linkedin.com/in/craigdp/📌 Don’t Forget to LIKE 👍, SUBSCRIBE 🔔 & COMMENT 💬 Below! ⭐ Produced by Icons of Real Estate - https://iconsofrealestate.com/

  19. 15

    One Step Closer to a Village: Co-Ops, Co-Living & Relearning Human Connection

    🚀 In this episode, we explore how cooperative living and sustainable business models are reshaping modern communities. Featuring Alex Jarrett and Daniel Trenner, the conversation dives into co-living, intergenerational housing, human-powered transportation, and the future of community-centered living. Learn how these innovative approaches address affordability, reduce environmental impact, and combat social isolation.🎧 Hosted by: Craig Della Penna👤 Guest:🏡 Alex Jarrett – Co-Founder of Pedal People Cooperative & City Council PresidentAlex Jarrett is the co-founder of Pedal People Cooperative, a worker-owned business in Northampton, Massachusetts that hauls trash, recycling, and compost by bicycle with trailers carrying up to 300 pounds. Since its founding in 2002, Pedal People has become a model for sustainable, human-powered urban transport. In addition to his work with the co-op, Alex shares insights on cooperative business models, community sustainability, and innovative solutions for reducing reliance on fossil fuels.🏡 Daniel Trenner – Professional Dancer & Co-Living InnovatorDaniel Trenner is a professional dancer, celebrating his 50th year in dance in 2026. He toured full time performing and teaching in the 80s and 90s. During his travels he was a guest in a number of multigenerational households, which inspired him to create a new kind of living arrangement back home in Florence, MA. In 2008, he purchased and renovated a home to support intergenerational co-living — where in place of blood family, he has built an intentional, non-blood household. Over 17 years, more than 100 residents have shared in the experience.💡 What You’ll Learn:✔️ How cooperative living models create stronger communities✔️ The benefits of human-powered, low-carbon business systems✔️ How intergenerational housing combats loneliness and supports aging✔️ Key challenges in co-living (insurance, zoning, financing)✔️ Practical strategies for building successful shared living environments🎵 Whether you're an investor, agent, or homebuyer, this episode offers valuable insights!💼 Connect with Alex Jarrett:🌐 Website → http://weatherbeard.com/flo-op🌐 Website → http://sharett.org/🌐 Website → http://pedalpeople.coop/💼 Connect with Daniel Trenner:🌐 Website → https://danieltrenner.com/📘 Facebook → https://www.facebook.com/search/top?q=daniel%20trenner🎧 Follow Craig Della Penna:🌐 Website → https://www.greenwaysolutions.org/🌐 Website → https://www.northamptonrealtor.com/🌐 Website →https://www.sugar-maple-inn.com/📷 Instagram → https://www.instagram.com/craigdp413/🔗 LinkedIn → https://www.linkedin.com/in/craigdp/📌 Don’t Forget to LIKE 👍, SUBSCRIBE 🔔 & COMMENT 💬 Below! ⭐ Produced by Icons of Real Estate - https://iconsofrealestate.com/

  20. 14

    Connecting Communities: Hudson Valley's Rail Trail Success - EP 21

    🚀 In this episode, we sit down with Jeff Anzevino, Director of Land Use Advocacy at Scenic Hudson, to explore how rail trails are reshaping communities across the Hudson Valley. From abandoned railroads to thriving public spaces, Jeff shares how projects like Walkway Over the Hudson and the Empire State Trail are driving economic growth, tourism, and community connection.🎧 Hosted by: Craig Della Penna👤 Guest:🏡 Jeff Anzevino – Director of Land Use AdvocacyJeffrey Anzevino, AICP is the Director of Land Use Advocacy at Scenic Hudson, where he advances resilient, sustainable riverfront development and expands public access to the Hudson River. He manages key projects like the Westchester RiverWalk extension under the Governor Mario M. Cuomo Bridge and co-authored Revitalizing Hudson Riverfronts, which earned a U.S. EPA Environmental Quality Award. A certified planner and adjunct instructor at Marist College, Jeff blends his professional expertise with a lifelong passion for cycling, photography, and the Hudson River.💡 What You’ll Learn:✔️ How rail trails evolved from abandoned railroads into connected regional systems✔️ The three phases of trail development: segments → connections → community integration✔️ How trails boost local economies and revitalize small towns✔️ The role of zoning, planning, and public perception in trail success✔️ Why trails act as “third places” that strengthen community and well-being🎮 Watch now for expert insights!🎵 Whether you're an investor, planner, or outdoor enthusiast, this episode offers valuable insights!💼 Connect with Jeff Anzevino:🌐 Website → https://www.scenichudson.org/🌐 Website → https://walkway.org/📸 Instagram → https://www.instagram.com/jeffrey_anzevino/🔗 LinkedIn → https://www.linkedin.com/in/jeffrey-anzevino-aicp-he-him-his-2200499a/🎧 Follow Craig Della Penna:🌐 Website → https://www.greenwaysolutions.org/🌐 Website → https://tinyurl.com/AboutXNHTrail🌐 Website → https://www.xnhat.org/🌐 Website → https://www.northamptonrealtor.com/🌐 Website →https://www.sugar-maple-inn.com/📷 Instagram → https://www.instagram.com/craigdp413/🔗 LinkedIn → https://www.linkedin.com/in/craigdp/📌 Don’t Forget to LIKE 👍, SUBSCRIBE 🔔 & COMMENT 💬 Below! ⭐ Produced by Icons of Real Estate - https://iconsofrealestate.com/

  21. 13

    An 83-Mile Cycling Route Through New Hampshire You’ve Never Heard Of - EP 20

    🚀 Marianne Borowski joins us to discuss the 83-mile Cross New Hampshire Adventure Trail and its rise as a top cycling route in New Hampshire. Learn how this trail connects communities, boosts cycling tourism, and transforms Northern New Hampshire into an emerging outdoor destination..🎧 Hosted by: Craig Della Penna👤 Guest:🏡 Marianne Borowski – Trail Developer & Outdoor Recreation AdvocateMarianne Borowski is the President and Founder of the Cross New Hampshire Adventure Trail and Vice President of the New Hampshire Rail Trails Coalition. A former protein biochemist during the early years of biotech, she shifted careers after moving to Mt. Washington Valley in 2003, becoming a cross-country ski instructor, later director of the Jackson Ski Touring Foundation ski school, and now a member of its Board of Directors. Today, she focuses on restoring, maintaining, and connecting rail trails across New Hampshire. An avid cyclist, Marianne has also biked across the U.S.💡 What You’ll Learn:✔️ How the Cross New Hampshire Adventure Trail was created✔️ The benefits of rail trails for tourism and local economies✔️ How to balance multi-use trails (bikes, ATVs, snowmobiles)✔️ The importance of community partnerships and local businesses✔️ Trail surface innovations that improve durability and accessibility🎵 Whether you're an investor, agent, or homebuyer, this episode offers valuable insights!💼 Connect with Marianne Borowski:📘 Facebook → https://facebook.com/crossnewhampshire📸 Instagram → https://instagram.com/crossnewhampshire🎧 Follow Craig Della Penna:🌐 Website → https://www.greenwaysolutions.org/🌐 Website → https://tinyurl.com/AboutXNHTrail🌐 Website → https://www.xnhat.org/🌐 Website → https://www.northamptonrealtor.com/🌐 Website →https://www.sugar-maple-inn.com/📷 Instagram → https://www.instagram.com/craigdp413/🔗 LinkedIn → https://www.linkedin.com/in/craigdp/📌 Don’t Forget to LIKE 👍, SUBSCRIBE 🔔 & COMMENT 💬 Below! ⭐ Produced by Icons of Real Estate - https://iconsofrealestate.com/

  22. 12

    Transformative Rail Trail Projects Across Massachusetts - EP 19

    🚀 In this episode, we sit down with Kurt Gaertner, Assistant Secretary of Environmental Policy at the Executive Office of Energy and Environmental Affairs, to explore how Massachusetts is leading the way in trail development. From the growth of the Mass Trails initiative to the vision behind long-distance rail trails like the Mass Central Rail Trail, Kurt shares insights on funding, environmental impact, equity, and the future of bike tourism.🎧 Hosted by: Craig Della Penna👤 Guest:🏡 Kurt Gaertner – Environmental Policy LeaderKurt Gaertner is the Assistant Secretary for Environmental Policy at the Executive Office of Energy and Environmental Affairs (EEA). In this role, he oversees land use, land conservation, water resource, and other environmental policies and programs designed to address climate change, promote sustainable development, and reduce resource consumption. He also represents the Executive Office on the MassTrails Team and has managed major projects through the Gateway City Parks Program, advancing public access and outdoor connectivity across Massachusetts.💡 What You’ll Learn:✔️ How Massachusetts prioritizes trail development at the state level✔️ The impact of the Mass Trails initiative and recent milestones✔️ How trails support environmental and transportation goals✔️ Funding opportunities and resources for local trail projects✔️ The future of long-distance trails and bike tourism in New England🎵 Whether you're an investor, agent, or homebuyer, this episode offers valuable insights!💼 Connect with Kurt Gaertner:🌐 Website → https://www.mass.gov/🔗 LinkedIn → https://www.linkedin.com/in/kurt-gaertner-13b245139🎧 Follow Craig Della Penna:🌐 Website → https://www.greenwaysolutions.org/🌐 Website → https://www.northamptonrealtor.com/🌐 Website →https://www.sugar-maple-inn.com/📷 Instagram → https://www.instagram.com/craigdp413/🔗 LinkedIn → https://www.linkedin.com/in/craigdp/📌 Don’t Forget to LIKE 👍, SUBSCRIBE 🔔 & COMMENT 💬 Below! ⭐ Produced by Icons of Real Estate - https://iconsofrealestate.com/

  23. 11

    Innovative Strategies for Bed and Breakfast Success - EP 18

    🚀 In this episode, hospitality expert David Mayfield shares powerful insights on growing and optimizing small lodging businesses. From dynamic pricing strategies to leveraging OTAs and building a regional hospitality network, this conversation explores how entrepreneurs can create thriving bed & breakfast ecosystems—especially in emerging tourism corridors like central Massachusetts.🎧 Hosted by: Craig Della Penna👤 Guest:🏡 David Mayfield – Hospitality Business Expert, Licensed Pilot & Real Estate InvestorDavid Mayfield is a hospitality business expert, licensed pilot, and real estate investor with over 17 years of industry experience. He has helped improve the performance of more than 2,200 properties, focusing on increasing occupancy, optimizing property management, streamlining operations, and elevating guest experience. Through his strategic guidance, David helps hospitality businesses grow efficiently and implement solutions that drive long-term success.💡 What You’ll Learn:✔️ How dynamic pricing can significantly increase revenue for small properties✔️ What OTAs (Online Travel Agencies) are and how to use them effectively✔️ Why building your own brand and direct booking system is critical✔️ How to create a regional bed & breakfast association for growth✔️ Marketing strategies that actually work for small hospitality businesses🎵 Whether you're an investor, agent, or homebuyer, this episode offers valuable insights!💼 Connect with David Mayfield:📘 Facebook → https://www.facebook.com/resnexus📸 Instagram → https://www.instagram.com/resnexus/🔗 LinkedIn → https://www.linkedin.com/company/resnexus/🎧 Follow Craig Della Penna:🌐 Website → https://www.greenwaysolutions.org/🌐 Website → https://www.northamptonrealtor.com/🌐 Website →https://www.sugar-maple-inn.com/📷 Instagram → https://www.instagram.com/craigdp413/🔗 LinkedIn → https://www.linkedin.com/in/craigdp/📌 Don’t Forget to LIKE 👍, SUBSCRIBE 🔔 & COMMENT 💬 Below! ⭐ Produced by Icons of Real Estate - https://iconsofrealestate.com/

  24. 10

    Innovative Strategies for Developing Sustainable Trail Networks - EP 17

    🚀 In this episode, trail advocate Don Burn shares decades of experience working to transform historic rail corridors, trolley lines, and aqueduct routes into modern shared-use trails. From his early exposure to the Illinois Prairie Path to championing trail networks in Massachusetts, Don explains the challenges of navigating utilities, working with state agencies, and convincing communities and developers to support trail connectivity. This conversation explores why trails should be designed as networks—not isolated paths—and how persistence, community engagement, and long-term vision can turn ambitious ideas into lasting public infrastructure.🎧 Hosted by: Craig Della Penna👤 Guest:🏡 Don Burn – Rail Trail Advocate & Retired Computer ConsultantDon Burn is a retired computer consultant and early supporter of the rail-to-trail movement. As a child, he explored the abandoned Chicago Aurora & Elgin electric rail line that later became the Illinois Prairie Path, where he met May Watts, the trail’s original proposer. After moving to Massachusetts, Don settled along the former Boston & Worcester Air Line Trolley corridor and began advocating in the early 1990s for its conversion into a shared-use trail. Over the years, he has worked with state agencies, businesses, and municipalities to advance trail projects, contributing concept plans, feasibility studies, and advocacy papers that continue to shape local trail development.💡 What You’ll Learn:✔️ How to develop trails on incomplete or complex rights-of-way✔️ Why trail systems should be designed as networks, not isolated routes✔️ Strategies for working with utilities, municipalities, and developers✔️ How advocacy, planning studies, and community education drive trail projects✔️ Lessons learned from decades of rail-trail development and activism🎵 Whether you're an investor, agent, or homebuyer, this episode offers valuable insights!💼 Connect with Don Burn:🌐 Email → [email protected]🎧 Follow Craig Della Penna:🌐 Website → https://www.greenwaysolutions.org/🌐 Website → https://www.northamptonrealtor.com/🌐 Website →https://www.sugar-maple-inn.com/📷 Instagram → https://www.instagram.com/craigdp413/🔗 LinkedIn → https://www.linkedin.com/in/craigdp/📌 Don’t Forget to LIKE 👍, SUBSCRIBE 🔔 & COMMENT 💬 Below! ⭐ Produced by Icons of Real Estate - https://iconsofrealestate.com/

  25. 9

    The Evolution of Rail Trail Advocacy in Natick - EP 16

    🚀 In this episode, longtime trail advocate George Eckert shares the story behind the development of the Natick rail trail in Massachusetts. From childhood memories walking old railroad tracks to decades of community advocacy, George discusses how local partnerships, grassroots efforts, and persistence helped turn a dormant rail corridor into a thriving community trail. The conversation explores the challenges of negotiating with rail companies, the role of friends groups and corporate partners, and how trails can transform transportation, recreation, and local economies.🎧 Hosted by: Craig Della Penna👤 Guest:🏡 George Eckert – Rail Trail Advocate & Community LeaderGeorge Eckert is a Vermont-based professional with a multifaceted career encompassing real estate, bed and breakfast operations, and rail trail development. He has been actively involved in discussions about accommodations near the Lamoille Valley Rail Trail, particularly in the context of planning cycling trips with bed and breakfast stops along the route. Eckert has also contributed to community engagement efforts related to the rail trail, including discussions about trail repairs and access improvements.💡 What You’ll Learn:✔️ How George’s early experiences with railroad corridors sparked a lifelong passion for trails✔️ The behind-the-scenes process of converting dormant rail lines into community trails✔️ The importance of advocacy groups, partnerships, and community engagement✔️ Creative initiatives like New Year’s celebrations and early “rustic trail” openings✔️ How rail trails evolve from recreation paths into vital transportation networks🎵 Whether you're an investor, agent, or homebuyer, this episode offers valuable insights!💼 Connect with George Eckert:📸 Facebook → https://www.facebook.com/george.eckert.1238🎧 Follow Craig Della Penna:🌐 Website → https://www.greenwaysolutions.org/🌐 Website → https://www.northamptonrealtor.com/🌐 Website →https://www.sugar-maple-inn.com/📷 Instagram → https://www.instagram.com/craigdp413/🔗 LinkedIn → https://www.linkedin.com/in/craigdp/📌 Don’t Forget to LIKE 👍, SUBSCRIBE 🔔 & COMMENT 💬 Below! ⭐ Produced by Icons of Real Estate - https://iconsofrealestate.com/

  26. 8

    Competitive Markets and Mortgage Strategies Unveiled - EP 15

    🚀 In this episode, host Craig Della Penna sits down with Lindsay Barron Labonte, a top-ranked mortgage professional with over 19 years of experience and Branch Manager of the Applied Mortgage Team at HMA Mortgage in Northampton, Massachusetts.Lindsay shares insights into why Western Massachusetts has become a desirable lifestyle destination for homebuyers, how today’s competitive housing market has transformed mortgage strategies, and the innovative programs lenders are using to help buyers compete against cash offers.The conversation also explores the rise of renovation loans, accessory dwelling units (ADUs), and how strong community involvement, local businesses, and rail trails shape the regional housing market. Lindsay explains how her team goes beyond traditional lending by building long-term relationships and supporting local nonprofits, businesses, and economic development.🎧 Hosted by: Craig Della Penna👤 Guest:🏡 Lindsay Barron Labonte – Mortgage Professional & Branch ManagerLindsay Barron LaBonte is a top-ranked mortgage professional with over 19 years of experience. As Branch Manager of the Applied Mortgage Team at HMA Mortgage in Northampton, MA, she has helped thousands achieve homeownership. Recognized as a Scotsman Guide Top 1% Woman Originator and featured in Mortgage Banking Magazine’s “Powerful Women in Mortgage Banking,” Lindsay also hosts the Real People, Real Estate podcast and serves on the board of the United Way of Franklin and Hampshire County.💡 What You’ll Learn:✔️ Why Western Massachusetts is attracting more homebuyers and relocations✔️ How buyers can compete in today’s competitive seller’s market✔️ The role of rail trails, local businesses, and culture in shaping housing demand✔️ Innovative mortgage strategies like platinum pre-approvals and cash buyer programs✔️ How community involvement strengthens both housing stability and local economies🎵 Whether you're an investor, agent, or homebuyer, this episode offers valuable insights!💼 Connect with Lindsay Barron Labonte:🌐 Website → https://www.hmamortgage.com/🎧 Follow Craig Della Penna:🌐 Website → https://www.greenwaysolutions.org/🌐 Website → https://www.northamptonrealtor.com/🌐 Website →https://www.sugar-maple-inn.com/📷 Instagram → https://www.instagram.com/craigdp413/🔗 LinkedIn → https://www.linkedin.com/in/craigdp/📌 Don’t Forget to LIKE 👍, SUBSCRIBE 🔔 & COMMENT 💬 Below! ⭐ Produced by Icons of Real Estate - https://iconsofrealestate.com/

  27. 7

    From Railways to Rail Trails: Belchertown's Journey - EP 14

    🚀 In this powerful and deeply personal episode, we sit down with longtime civic leader Dan Fitzpatrick, whose decades of service helped shape modern Belchertown. From transforming the school system and managing explosive population growth to leading one of Massachusetts’ most controversial rail trail battles, Dan shares behind-the-scenes stories of leadership, resistance, and perseverance.🎧 Hosted by: Craig Della Penna👤 Guest:🏡 Dan Fitzpatrick – Educator & Civic LeaderDan Fitzpatrick is a seasoned public administrator with extensive experience in local government leadership. He served as the Town Manager of Needham, Massachusetts, where he was recognized for his innovative approaches, including the implementation of outdoor Town Meetings during the COVID-19 pandemic. Fitzpatrick has been actively involved in professional organizations, serving on the leadership advisory board and credentialing advisory board of the International City/County Management Association (ICMA). He also co-founded Massachusetts Women Leading Government and served as president of the Massachusetts Municipal Management Association from 2009 to 2010. His contributions to local governance have been acknowledged through various awards and recognitions.💡 What You’ll Learn:✔️ How Belchertown grew from 4,500 to 15,000 residents✔️ The inside story of building three new schools✔️ Why the rail trail vote narrowly failed — and what happened next✔️ The challenges of leading during community division✔️ How long-term vision transforms rural towns🎵 Whether you're an investor, agent, or community leader, this episode offers valuable insights into vision-driven development and local governance.💼 Connect with Dan Fitzpatrick:🌐 Website → https://www.facebook.com/daniel.fitzpatrick.733/🎧 Follow Craig Della Penna:🌐 Website → https://www.greenwaysolutions.org/🌐 Website → https://www.northamptonrealtor.com/🌐 Website →https://www.sugar-maple-inn.com/📷 Instagram → https://www.instagram.com/craigdp413/🔗 LinkedIn → https://www.linkedin.com/in/craigdp/📌 Don’t Forget to LIKE 👍, SUBSCRIBE 🔔 & COMMENT 💬 Below! ⭐ Produced by Icons of Real Estate - https://iconsofrealestate.com/

  28. 6

    Revitalizing Ware: Community Development and Healthcare Visions - EP 13

    🚀 In this powerful episode, host Craig Della Penna sits down with longtime community leader Cynthia Allen Bourcier to discuss the future of Ware, Massachusetts. From rural healthcare reform and the repurposing vision for the former Mary Lane Hospital site to the expansion of the Mass Central Rail Trail, Cindy shares how volunteers shape the destiny of small towns. With over 40 years of nonprofit leadership experience, she reveals why stepping up matters, how persistence drives change, and what’s next for Ware’s renaissance.🎧 Hosted by: Craig Della Penna👤 Guest:🏡 Cynthia Allen Bourcier – Nonprofit Leader & Community Development AdvocateCynthia Allen Bourcier has over 40 years of experience in nonprofit leadership and community development. She has volunteered with organizations focused on parks and recreation, elder care, food access, and downtown revitalization in Ware, Massachusetts. Cynthia has served on multiple boards, helped lead Main Street business renewal efforts, and supported local initiatives such as the Friends of Mary Lane Hospital. She holds a B.A. in Management Science and has a professional background in operations project management.💡 What You’ll Learn:✔️ Why volunteer leadership is essential for small town survival✔️ The vision for redeveloping the former Mary Lane Hospital site✔️ How rural healthcare funding could transform Central Massachusetts✔️ The next steps for the Mass Central Rail Trail expansion in Ware✔️ How persistence and community advocacy shape long-term success🎵 Whether you're an investor, agent, or homebuyer, this episode offers valuable insights!💼 Connect with Cynthia Allen Bourcier:🌐 Website → https://www.facebook.com/p/Friends-of-the-Mary-Lane-Hospital-61557358145959/🎧 Follow Craig Della Penna:🌐 Website → https://www.greenwaysolutions.org/🌐 Website → https://www.northamptonrealtor.com/🌐 Website →https://www.sugar-maple-inn.com/📷 Instagram → https://www.instagram.com/craigdp413/🔗 LinkedIn → https://www.linkedin.com/in/craigdp/📌 Don’t Forget to LIKE 👍, SUBSCRIBE 🔔 & COMMENT 💬 Below! ⭐ Produced by Icons of Real Estate - https://iconsofrealestate.com/

  29. 5

    Building Massachusetts’ Trail Network: Inside MassDOT’s Vision - EP 12

    🚀 In this energizing episode, Craig Della Penna sits down with Peter Sutton, Bicycle and Pedestrian Program Coordinator at MassDOT, to explore the future of rail trails, active transportation, and statewide collaboration. From the 25th Annual Moving Together Conference to the ambitious expansion of the Mass Central Rail Trail, Peter shares how Massachusetts is transforming infrastructure to support biking, walking, and transit. We dive into funding breakthroughs, interagency partnerships, economic impact, cross-state trail connections, and what it will take to complete the most complex trail gaps left in the Commonwealth.🎧 Hosted by: Craig Della Penna👤 Guest:🏡 Peter Sutton – Bicycle & Pedestrian Program Coordinator, MassDOTPeter Sutton is the Bicycle and Pedestrian Program Coordinator at the Massachusetts Department of Transportation (MassDOT), based in Boston. In this role, he leads statewide initiatives to enhance walking and biking infrastructure, aiming to create a safer and more equitable transportation network. Sutton co-chairs the Massachusetts Bicycle and Pedestrian Advisory Board and chairs the "Moving Together" conference, which focuses on advancing non-motorized transportation. He has been instrumental in expanding shared-use paths across the state, contributing to the addition of 15 miles of such paths in 2024 alone. Sutton is also actively involved in community engagement, volunteering with walking and biking groups, and has cycled nearly every greenway from Provincetown to Williamstown. 💡 What You’ll Learn:✔️ Key takeaways from the 25th Annual Moving Together Conference✔️ How the Mass Trails Team breaks down silos between state agencies✔️ The economic impact and future of the Mass Central Rail Trail✔️ Why “Complete Streets” policy is reshaping Massachusetts infrastructure✔️ How advocates and residents can influence trail projects through public engagement🎵 Whether you're an investor, agent, advocate, or community leader, this episode offers powerful insight into the economic and cultural transformation happening along Massachusetts’ trail corridors.💼 Connect with Peter Sutton:🌐 Website → https://www.mass.gov/orgs/massachusetts-department-of-transportation📸 Instagram → https://www.instagram.com/massdotinfo💼 LinkedIn → https://www.linkedin.com/company/massachusetts-department-of-transportation🎧 Follow Craig Della Penna:🌐 Website → https://www.greenwaysolutions.org/🌐 Website → https://www.northamptonrealtor.com/🌐 Website →https://www.sugar-maple-inn.com/📷 Instagram → https://www.instagram.com/craigdp413/🔗 LinkedIn → https://www.linkedin.com/in/craigdp/📌 Don’t Forget to LIKE 👍, SUBSCRIBE 🔔 & COMMENT 💬 Below! ⭐ Produced by Icons of Real Estate - https://iconsofrealestate.com/

  30. 4

    Cross-Country Cycling and Community Trails Impact - EP 11

    🚀 In this inspiring episode, we sit down with Brian Sutton—former emergency physician, medical director, and founder of his own occupational health clinic—to explore his remarkable journey from hospital medicine to cycling across America on the Great American Rail Trail. From riding through Yellowstone and battling headwinds in Montana to launching his FAA aviation medical examiner practice in Westfield, Brian shares powerful insights on resilience, reinvention, and the life-changing impact of active living.🎧 Hosted by: Craig Della Penna👤 Guest:🏡 Brian Sutton – Emergency Physician & Founder of Westfield Occupational Health ClinicDr. Brian Sutton is a lifelong Western Massachusetts resident and graduate of Fairfield University and the University of Massachusetts Medical School. He spent 22 years as an emergency physician at Noble Hospital before serving five years as Medical Director for Baystate Health Urgent Care. Now the founder of his own occupational health clinic in Westfield, Dr. Sutton continues to blend his medical expertise with a passion for wellness and active living. An avid cyclist, he completed a cross-country ride along the Great American Rail Trail in 2023.💡 What You’ll Learn:✔️ Why emergency medicine is “a young person’s game” and how Brian transitioned careers at 55✔️ The logistics, challenges, and realities of biking 50–60 miles a day across 14 states✔️ The health science behind daily exercise and cardiovascular longevity✔️ How rail trails revitalize communities and drive economic development✔️ Lessons from Yellowstone wildlife encounters, RV support crews, and gravel road survival🎵 Whether you're an investor, agent, or homebuyer, this episode offers valuable insights!💼 Connect with Brian Sutton:🔗 LinkedIn → https://www.linkedin.com/in/brian-p-sutton-md-facep-148b2284/🎧 Follow Craig Della Penna:🌐 Website → https://www.greenwaysolutions.org/🌐 Website → https://www.northamptonrealtor.com/🌐 Website →https://www.sugar-maple-inn.com/📷 Instagram → https://www.instagram.com/craigdp413/🔗 LinkedIn → https://www.linkedin.com/in/craigdp/📌 Don’t Forget to LIKE 👍, SUBSCRIBE 🔔 & COMMENT 💬 Below! ⭐ Produced by Icons of Real Estate - https://iconsofrealestate.com/

  31. 3

    Innovation on the Move: Videography and Biking Paths - EP 10

    🚀 In this episode, Craig Della Penna sits down with filmmaker Tom Adam, founder of  Reelife  Documentary Productions, to explore the intersection of storytelling, rail trails, biking culture, and community transformation. From analog tape decks to digital filmmaking, and from grassroots trail advocacy to cross-country bike adventures, this conversation highlights how media and movement shape thriving communities.🎧 Hosted by: Craig Della Penna👤 Guest:🏡 Tom Adams – Founder & Director,  Reelife Documentary ProductionsTom Adams is the Founder and Director of Reelife Documentary Productions, creating educational and socially impactful media since 1996. A three-time Telly Award winner with over 30 years of experience, he has produced films for PBS, museums, and nonprofits, and directed more than 300 TV commercials. Based in Williamsburg, Massachusetts, Tom holds a B.A. in Communications from UMass Amherst.💡 What You’ll Learn:✔️ How to align creative passion with paying clients✔️ The evolution from analog videotape to modern digital production✔️ The economic and cultural impact of rail trails in Massachusetts✔️ Lessons from town meeting controversies and community votes✔️ The rise of bike tourism and long-distance trail adventures🎵 Whether you're an investor, agent, or homebuyer, this episode offers valuable insights!💼 Connect with Tom Adams:🌐 Website → https://www.reelifeproductions.com/📘 Facebook →https://www.facebook.com/reelife📷 Instagram → https://www.instagram.com/reelife_productions/🔗 LinkedIn → https://www.linkedin.com/in/tomadams2/🎧 Follow Craig Della Penna:🌐 Website → https://www.greenwaysolutions.org/🌐 Website → https://www.northamptonrealtor.com/🌐 Website →https://www.sugar-maple-inn.com/📷 Instagram → https://www.instagram.com/craigdp413/🔗 LinkedIn → https://www.linkedin.com/in/craigdp/📌 Don’t Forget to LIKE 👍, SUBSCRIBE 🔔 & COMMENT 💬 Below! ⭐ Produced by Icons of Real Estate - https://iconsofrealestate.com/

  32. 2

    Championing Access for All: Rail Trail Innovations - EP 9

    🚀 In this powerful and inspiring episode, host Craig Della Penna sits down with Steven Hawk, a wheelchair user and passionate rail trail advocate from Ware, Massachusetts. Steven shares how accessible trail design has transformed his independence, mobility, and connection to community. Together, they explore why ADA-compliant public spaces matter, how residents can advocate for inclusion, and how rail trails can spark downtown revitalization, economic growth, and a stronger sense of belonging for everyone.🎧 Hosted by: Craig Della Penna👤 Guest:🏡 Steven Hawk – Community Advocate & Accessible Trail LeaderSteven Hawk is a resident of Ware, Massachusetts, and an active user of the local Rail Trail. As a wheelchair user, Steven relies on the trail several times a week for transportation, grocery shopping, visiting family and friends, and enjoying time outdoors. His experience highlights the importance of accessible community spaces that support independence, connection, and mobility for people of all abilities.💡 What You’ll Learn:✔️ How accessible design supports independence and mobility✔️ Why ADA-compliant trails benefit all ages and abilities✔️ Common accessibility challenges in rail trail development✔️ How residents can advocate effectively with local leaders✔️ How rail trails strengthen communities and local economies🎵 Whether you're a planner, advocate, or community leader, this episode offers valuable insights!💼 Connect with Steven Hawk:🌐 Email → [email protected]🎧 Follow Craig Della Pena:🌐 Website → https://www.greenwaysolutions.org/🌐 Website → https://www.northamptonrealtor.com/🌐 Website →https://www.sugar-maple-inn.com/📷 Instagram → https://www.instagram.com/craigdp413/🔗 LinkedIn → https://www.linkedin.com/in/craigdp/📌 Don’t Forget to LIKE 👍, SUBSCRIBE 🔔 & COMMENT 💬 Below! ⭐ Produced by Icons of Real Estate - https://iconsofrealestate.com/

  33. 1

    Exploring Conservation: Farming, Biking, and Community Ties - EP 8

    🚀 In this episode, host Craig Della Penna sits down with conservationist and organic farmer Kristen Sykes to explore the powerful connection between local recreation, sustainable land use, and vibrant communities. Kristen shares firsthand stories from her organic farm, discusses the importance of bike and pedestrian infrastructure, and explains how accessible trails, local farms, and small businesses strengthen public health, economic resilience, and community bonds.🎧 Hosted by: Craig Della Penna👤 Guest:🏡 Kristen Sykes – Conservationist, Organic Farmer & Active Transportation AdvocateKristen Sykes is a conservationist, organic farmer, and advocate for biking and pedestrian infrastructure. She has been actively involved in advancing sustainable land use, active transportation, and community-based environmental initiatives. Through her work in conservation and agriculture, Kristen promotes healthier ecosystems and resilient local communities, while championing safe, accessible mobility options for all.💡 What You’ll Learn:✔️ Why close-to-home recreation is vital for community health and connection✔️ How local farms and trails strengthen local economies✔️ The benefits of bike and pedestrian infrastructure for all road users✔️ Challenges and opportunities in expanding safe, accessible pathways✔️ How conservation and mobility help communities adapt for the future🎵 Whether you're a planner, advocate, or community-minded resident, this episode offers valuable insights!💼 Connect with Kristen Sykes:📘 Facebook → https://www.facebook.com/kristen.sykes2/📸 Instagram → https://www.instagram.com/super.syked🔗 LinkedIn → https://www.linkedin.com/in/kristen-m-sykes/🎧 Follow Craig Della Pena:🌐 Website → https://www.greenwaysolutions.org/🌐 Website → https://www.northamptonrealtor.com/🌐 Website →https://www.sugar-maple-inn.com/📷 Instagram → https://www.instagram.com/craigdp413/🔗 LinkedIn → https://www.linkedin.com/in/craigdp/📌 Don’t Forget to LIKE 👍, SUBSCRIBE 🔔 & COMMENT 💬 Below! ⭐ Produced by Icons of Real Estate - https://iconsofrealestate.com/

  34. 0

    Exploring Community Life in Northampton and Beyond - EP 7

    🚀 In this thoughtful episode, host Craig Della Penna speaks with community advocate and former communications executive David Hallerman about the future of Northampton, Massachusetts. The conversation explores bike trails and e-bike regulation, eminent domain and downtown revitalization, community-building beyond screens, sustainable transportation ideas, and how culture, history, and even time itself shape thriving places.🎧 Hosted by: Craig Della Penna👤 Guest:🏡 David Hallerman – Community Advocate & Former Communications ExecutiveDavid Hallerman is a retired communications professional now based in Western Massachusetts. He previously served as Chief Marketing Officer at In Place ReDesign Architecture, a firm specializing in aging-in-place design and planning. Before that, he worked as a principal analyst at eMarketer, focusing on U.S. advertising and digital media trends. Active in his community, David participates in events such as the “Will Bike 4 Food” charity ride for the Food Bank of Western Massachusetts, does photography for Grow Food Northampton, and volunteers with Northampton Neighbors. He is an avid cyclist, photographer, and astrologer, and resides in Florence, Massachusetts.💡 What You’ll Learn:✔️ The debate around e-bikes and motorized vehicles on shared-use trails✔️ How rail trails function as modern community connectors✔️ The role of eminent domain and incentives in downtown revitalization✔️ Ways communities can encourage real human connection beyond screens✔️ Sustainable, people-centered ideas shaping Northampton’s future🎵 Whether you're a planner, resident, or community leader, this episode offers valuable insights!💼 Connect with David Hallerman:🔗 LinkedIn → https://www.linkedin.com/in/hallerman/🎧 Follow Craig Della Pena:🌐 Website → https://www.greenwaysolutions.org/🌐 Website → https://www.northamptonrealtor.com/🌐 Website →https://www.sugar-maple-inn.com/📷 Instagram → https://www.instagram.com/craigdp413/🔗 LinkedIn → https://www.linkedin.com/in/craigdp/📌 Don’t Forget to LIKE 👍, SUBSCRIBE 🔔 & COMMENT 💬 Below! ⭐ Produced by Icons of Real Estate - https://iconsofrealestate.com/

  35. -1

    From Railways to Pathways: A Journey in Trails - EP 1 - Part 3

    🚀  In Part 3 of this special episode of Roads Less Traveled, the mic is turned toward the show’s own host, Craig Della Penna. Craig shares the remarkable journey that shaped his life’s work, from growing up alongside railroads to becoming one of North America’s leading advocates for rail trails and a real estate professional who proves that living near a trail is not a liability, but a lifestyle advantage. Through history, advocacy, books, speaking, and real estate, Craig reveals how purpose, persistence, and community connection can redefine places long overlooked.🎧 Hosted by: Craig Della Penna💡 What You’ll Learn:✔️ How railroads and rail trails shaped Craig’s life and career✔️ Why rail trails act as powerful “third places” for communities✔️ How trails can revive underinvested gateway cities✔️ Why living near a trail enhances property value and lifestyle✔️ How purpose-driven work can evolve across careers and decades🎵 Whether you're passionate about community, real estate, or place-based living, this episode offers powerful insights!🎧 Follow Craig Della Pena:🌐 Website → https://www.greenwaysolutions.org/🌐 Website → https://www.northamptonrealtor.com/🌐 Website →https://www.sugar-maple-inn.com/📷 Instagram → https://www.instagram.com/craigdp413/🔗 LinkedIn → https://www.linkedin.com/in/craigdp/📌 Don’t Forget to LIKE 👍, SUBSCRIBE 🔔 & COMMENT 💬 Below! ⭐ Produced by Icons of Real Estate - https://iconsofrealestate.com/

  36. -2

    From Railways to Pathways: A Journey in Trails - EP 1 - Part 2

    🚀 In Part 2 of this special episode of Roads Less Traveled, the mic is turned toward the show’s own host, Craig Della Penna, as he shares the deeper chapters of his life’s work. From fierce rail-trail battles and community resistance to rebuilding abandoned rail corridors across Massachusetts and the Northeast, Craig reflects on advocacy, history, resilience, and why trails are not a liability—but a lifestyle and community advantage. This episode weaves together real estate, preservation, personal history, and the long arc of social change.🎧 Hosted by: Craig Della Penna💡 What You’ll Learn:✔️ The “three stages of truth” and how new ideas gain acceptance over time✔️ Why rail trails faced fierce opposition—and how that changed✔️ How Craig helped resurrect projects once voted down✔️ The strategy behind rebranding trails as greenways✔️ Why trails enhance real estate value and community identity🎵 Whether you're a real estate professional, advocate, or community builder, this episode offers powerful perspective and inspiration!🎧 Follow Craig Della Pena:🌐 Website → https://www.greenwaysolutions.org/🌐 Website → https://www.northamptonrealtor.com/🌐 Website →https://www.sugar-maple-inn.com/📷 Instagram → https://www.instagram.com/craigdp413/🔗 LinkedIn → https://www.linkedin.com/in/craigdp/📌 Don’t Forget to LIKE 👍, SUBSCRIBE 🔔 & COMMENT 💬 Below! ⭐ Produced by Icons of Real Estate - https://iconsofrealestate.com/

  37. -3

    From Railways to Pathways: A Journey in Trails - EP 1 - Part 1

    🚀 In this special “Flip the Script” episode, host Craig Della Penna steps out from behind the mic to share the remarkable journey that shaped his life’s mission. He opens up about his early fascination with transportation, life in trolley-built neighborhoods, dramatic shifts in New England’s mill towns, and how abandoned rail corridors became the backbone of modern linear parks. Craig also reveals how one second-grade moment ignited a lifelong commitment to truth, advocacy, and “getting places to YES.” This episode blends history, humor, advocacy, and real estate insight into one deeply personal narrative.🎧 Hosted by: Craig Della Penna💡 What You’ll Learn:✔️ How growing up in a trolley neighborhood shaped Craig’s worldview✔️ Why New England has the densest dead-rail corridor network in the country✔️ How industrial decline led to today’s vibrant rail trail renaissance✔️ The origin of Craig’s passion for truth and community advocacy✔️ How one book, one publisher, and one donor launched his rail trail career🎵 Whether you're an investor, agent, trail lover, or community builder, this episode offers valuable insights!🎧 Follow Craig Della Pena:🌐 Website → https://www.greenwaysolutions.org/🌐 Website → https://www.northamptonrealtor.com/🌐 Website →https://www.sugar-maple-inn.com/📷 Instagram → https://www.instagram.com/craigdp413/🔗 LinkedIn → https://www.linkedin.com/in/craigdp/📌 Don’t Forget to LIKE 👍, SUBSCRIBE 🔔 & COMMENT 💬 Below! ⭐ Produced by Icons of Real Estate - https://iconsofrealestate.com/

  38. -4

    Trailblazing the East Coast: A Journey of Greenways - EP 6

    🚀 In this episode of Trails, Transit & Transformation, host Craig Della Penna sits down with Bill O’Neill, retired engineer, principal at Fuss & O’Neill, and one of the early champions behind the East Coast Greenway. Often called the Father of the East Coast Greenway, Bill reflects on his decades of work connecting communities through trails, family involvement in multi-use path planning, and the powerful economic and cultural ripple effects of greenway development across New England and beyond. From the inaugural Boston-to-D.C. ride to cross-border collaboration with Canada, and even the creation of Connecticut’s Greenway license plate program, this conversation captures the passion and persistence behind a movement that redefined how America connects its people and places.🎧 Hosted by: Craig Della Penna 👤 Guest: 🏡 Bill O’Neill – Retired Engineer, Founding Advocate of the East Coast GreenwayBill O’Neill is a seasoned advocate for multi-use trails in Connecticut and Rhode Island, with a focus on the East Coast Greenway. He served as the former chair of the Connecticut Greenways Council and has been instrumental in advancing the Charter Oak Greenway in Manchester, Connecticut. O’Neill has also been involved in the development of the William C. O’Neill Bike Path in Rhode Island, previously known as the South County Bike Path, which repurposes a former railroad corridor into a recreational trail. His contributions to trail development have been recognized in various local media outlets.💡 What You’ll Learn: ✔️ How Bill O’Neill’s family helped shape the East Coast Greenway’s early years ✔️ Behind-the-scenes stories from the inaugural Boston-to-D.C. Greenway ride ✔️ The evolution of cross-border cooperation with Canada’s trail network ✔️ How Connecticut’s trail census and ROI studies influence funding decisions ✔️ Why trails drive local economies and revitalize small towns🎵 Whether you’re a trail builder, planner, or cyclist, this episode will leave you inspired by the persistence and creativity behind America’s greenway movement.💼 Connect with Bill O’Neill:🌐 East Coast Greenway → https://greenway.org🎧 Follow Craig Della Penna:🌐 Website → https://www.greenwaysolutions.org/🌐 Website → https://www.northamptonrealtor.com/🌐 Website →https://www.sugar-maple-inn.com/📷 Instagram → https://www.instagram.com/craigdp413/🔗 LinkedIn → https://www.linkedin.com/in/craigdp/⭐ Produced by Icons of Real Estate - https://iconsofrealestate.com/

  39. -5

    Exploring New England's Trail Magic and Rail History - EP 5

    🚀 In this inspiring episode, host Craig Della Penna sits down with engineer and lifelong rail trail enthusiast Michael Akrep to discuss the magic of New England’s historic rail trails. From abandoned railway routes to vibrant biking corridors, Michael shares stories of adventure, preservation, and the communities thriving along these trails. They explore the Lamoille Valley and Mass Central Rail Trails, the growing rail-to-trail movement, and how cycling tourism is reviving local economies across Massachusetts and Vermont.🎧 Hosted by: Craig Della Penna 👤 Guest: 🏡 Michael Akrep – Engineer, Rail Trail Enthusiast & Former Bike Tour GuideMichael Akrep is an engineer and lifelong rail trail enthusiast who grew up in Eastern Massachusetts and now calls Western Massachusetts home. With a passion for exploring both abandoned railroad grades and developed trails, he has combined his love of cycling with professional experience as a bike tour guide, leading tours across Massachusetts, Rhode Island, Connecticut, New Hampshire, and Vermont.💡 What You’ll Learn: ✔️ The hidden beauty and history behind New England’s rail trails ✔️ How rail-to-trail projects are revitalizing local communities ✔️ Michael’s most memorable cycling adventures and A-to-B ride philosophy ✔️ The tools and maps every rail trail explorer should know ✔️ How rail trails connect people, history, and health across the region🎵 Whether you're an investor, agent, or outdoor enthusiast, this episode offers valuable insights into the intersection of recreation, history, and community.💼 Connect with Michael Akrep:🌐 Website → https://www.polarfocus.com/📘 Facebook → https://www.facebook.com/michael.akrep🔗 LinkedIn → https://www.linkedin.com/in/mike-akrep-40945431🏡 Sharing → https://ridewithgps.com/routes/16359696 — Michael’s go-to loop ride, a beautiful 20+ mile route packed with views and great flow.🏡 Sharing → https://lnk.ink/pd0Gi — A folder of stunning photos from the places we talk about — perfect visuals to bring the stories to life!🎧 Follow Craig Della Penna:🌐 Website → https://www.greenwaysolutions.org/🌐 Website → https://www.northamptonrealtor.com/🌐 Website →https://www.sugar-maple-inn.com/📷 Instagram → https://www.instagram.com/craigdp413/🔗 LinkedIn → https://www.linkedin.com/in/craigdp/⭐ Produced by Icons of Real Estate - https://iconsofrealestate.com/

  40. -6

    Connecting Communities: The Future of Trail Infrastructure - EP 4

    🚀 In this insightful episode, host Craig Della Penna sits down with Bruce Donald, Southern New England Manager for the East Coast Greenway Alliance, to explore how regional trail systems are transforming communities. From the challenges of long-term rail-to-trail projects to the power of data-driven advocacy, Bruce shares decades of experience in trail planning, funding, and community partnerships. Together, they uncover how sustainable mobility links cities, boosts local economies, and improves quality of life across New England.🎧 Hosted by: Craig Della Penna👤 Guest: 🏡 Bruce Donald – Southern New England Manager, East Coast Greenway AllianceBruce Donald is the Southern New England Manager for the East Coast Greenway Alliance, based in Farmington, Connecticut, overseeing greenway development, advocacy, and volunteer coordination across Connecticut, Rhode Island, and eastern Massachusetts. He served as president of the Farmington Valley Trails Council for 12 years and was appointed chair of the Connecticut Greenways Council in 2014. In recognition of his trail advocacy, the Connecticut General Assembly issued an official citation honoring his contributions in 2016. Bruce also brings deep financial and consulting expertise from nearly two decades in investment, management, and banking across Boston, New York, Hartford, and Beijing. An avid cyclist and published historian, he authored a Civil War–era book based on his great-great-grandfather’s letters.💡 What You’ll Learn: ✔️ Why regional trail connections matter for mobility, recreation, and community health ✔️ The vision and progress of the 3,000-mile East Coast Greenway ✔️ Overcoming funding challenges and securing state and federal support ✔️ The importance of local advocacy, data collection, and “trail census” initiatives ✔️ Stories of trail opponents turned advocates — and the power of persistence in community change🎵 Whether you're an investor, planner, or outdoor enthusiast, this episode delivers lessons in leadership, patience, and purpose.💼 Connect with Bruce Donald:🌐 Website → https://greenway.org/📘 Facebook→ https://www.facebook.com/bruce.donald.758🎧 Follow Craig Della Penna:🌐 Website → https://www.greenwaysolutions.org/🌐 Website → https://www.northamptonrealtor.com/🌐 Website →https://www.sugar-maple-inn.com/📷 Instagram → https://www.instagram.com/craigdp413/🔗 LinkedIn → https://www.linkedin.com/in/craigdp/⭐ Produced by Icons of Real Estate - https://iconsofrealestate.com/

  41. -7

    The Impact of Trails on Local Real Estate - EP 3

    🚀 Host Craig Della Penna talks with Kristin Vevon, realtor with Murphy’s Realtors and founder of The Real Estate Book of Western Massachusetts, about the growing connection between real estate, lifestyle, and greenway development. They explore how properties near bike trails are reshaping communities, the impact of print-to-digital transitions in real estate marketing, and the economic revival brought by trail-based developments.🎧 Hosted by: Craig Della Penna👤 Guest: 🏡 Kristin Vevon – Realtor & Former Publisher, Murphy’s RealtorsKristin Vevon is a trusted real estate agent with The Murphys REALTORS® in Western Massachusetts, licensed since 1992 and serving communities across the Pioneer Valley. A Whately resident since 1982, she founded The Real Estate Book of Western Massachusetts in 1988 to help local buyers and sellers connect—with the goal of making home ownership both informative and enjoyable. Over the past five years, Kristin has closed numerous transactions totaling over $7 million in sales, demonstrating a consistent track record of success in markets like Florence, Northampton, and beyond.💡 What You’ll Learn: ✔️ Why trail-based housing is in high demand ✔️ How greenways drive community and economic growth ✔️ The transition from print to digital real estate marketing ✔️ Insights into the Trails Edge Commons project in Northampton ✔️ How lifestyle and sustainability shape modern homebuyers’ choices🎵 Discover how real estate, nature, and community come together along New England’s rail trails.💼 Connect with Kristin Vevon:🌐 Website → https://pioneervalleyhome.com/🎧 Follow Craig Della Penna:🌐 Website → https://www.greenwaysolutions.org/🌐 Website → https://www.northamptonrealtor.com/🌐 Website →https://www.sugar-maple-inn.com/📷 Instagram → https://www.instagram.com/craigdp413/🔗 LinkedIn → https://www.linkedin.com/in/craigdp/⭐ Produced by Icons of Real Estate - https://iconsofrealestate.com/

  42. -8

    Community Partnerships: Building a Thriving Local Economy - EP 2

    🚀 In this episode, host Craig Della Penna sits down with Tara Brewster, VP of Business Development at Greenfield Savings Bank, to explore the power of community banking, social entrepreneurship, and kindness in local development. Tara shares her journey from entrepreneur to banker, her passion for giving back, and her vision for Western Massachusetts’ future. From partnerships between nonprofits and businesses, to the impact of kindness and collaboration, this episode shines a light on building stronger communities together.🎧 Hosted by: Craig Della Penna👤 Guest: 🏡 Tara Brewster – VP of Business Development, Greenfield Savings Bank & Community LeaderTara Brewster is the Vice President of Business Development and Director of Philanthropy at Greenfield Savings Bank, where she leverages her entrepreneurial experience and strong community ties to foster partnerships and philanthropic initiatives across Western Massachusetts. A respected community leader, she’s been honored as a BusinessWest 40 Under Forty alum and recognized as a Difference Maker in 2022 for her tireless work raising funds and awareness for area nonprofits. In addition, she was recently appointed as a trustee for the Community Foundation of Western Massachusetts, reinforcing her influence in helping drive equity and opportunity in the region.💡 What You’ll Learn: ✔️ The difference between community mutual banks and “too big to fail” stock banks ✔️ How social entrepreneurship drives innovation and community impact ✔️ Real-world examples of nonprofits and businesses partnering for change ✔️ The importance of kindness, relationships, and helping others ✔️ Why Western Massachusetts is a unique and thriving place to live ✔️ Tara’s vision for the region’s growth and collaboration in the next decade🎵 Whether you’re a business owner, nonprofit leader, or simply passionate about community, this episode will inspire you to see how kindness and collaboration can transform local life.💼 Connect with Tara Brewster:🌐 Website → https://www.greenfieldsavings.com/💼 LinkedIn → https://www.linkedin.com/in/taratbrewster/🎧 Follow Craig Della Penna:🌐 Website → https://www.greenwaysolutions.org/🌐 Website → https://www.northamptonrealtor.com/🌐 Website →https://www.sugar-maple-inn.com/📷 Instagram → https://www.instagram.com/craigdp413/🔗 LinkedIn → https://www.linkedin.com/in/craigdp/⭐ Produced by Icons of Real Estate - https://iconsofrealestate.com/

  43. -9

    Intro

    Passionate about real estate, rail trails, and the lifestyle they inspire? Join Craig Della Penna—Realtor and trail advocate—as he shares insights on buying homes near green corridors, bike tourism, and B&B opportunities. With decades of experience turning historic railroads into thriving assets, Craig offers inspiring stories, tips, and insider knowledge. Whether you’re a homebuyer, investor, or trail enthusiast, Roads Less Travelled releases new episodes every two weeks.

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ABOUT THIS SHOW

Passionate about real estate, rail trails, and the lifestyle they inspire? Join Craig Della Penna—Realtor and trail advocate—as he shares insights on buying homes near green corridors, bike tourism, and B&B opportunities. With decades of experience turning historic railroads into thriving assets, Craig offers inspiring stories, tips, and insider knowledge. Whether you’re a homebuyer, investor, or trail enthusiast, Roads Less Travelled releases new episodes every two weeks.

HOSTED BY

Craig Della Pena

CATEGORIES

Frequently Asked Questions

How many episodes does Roads Less Travelled have?

Roads Less Travelled currently has 43 episodes available on PodParley. New episodes are automatically indexed when they're published to the podcast feed.

What is Roads Less Travelled about?

Passionate about real estate, rail trails, and the lifestyle they inspire? Join Craig Della Penna—Realtor and trail advocate—as he shares insights on buying homes near green corridors, bike tourism, and B&B opportunities. With decades of experience turning historic railroads into thriving assets,...

How often does Roads Less Travelled release new episodes?

Roads Less Travelled has 43 episodes. Check the episode list to see recent publication dates and frequency.

Where can I listen to Roads Less Travelled?

You can listen to Roads Less Travelled on PodParley by clicking any episode. We provide an embedded audio player for direct listening, and you can also subscribe via your preferred podcast app using the RSS feed.

Who hosts Roads Less Travelled?

Roads Less Travelled is created and hosted by Craig Della Pena.
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