764: The Happiest Challenge That Ever Sailed: 10 Hours on “it’s a small world” episode artwork

EPISODE · Apr 18, 2025 · 36 MIN

764: The Happiest Challenge That Ever Sailed: 10 Hours on “it’s a small world”

from Main Street Magic - A Walt Disney World Podcast · host Jeremy Stein

We take you behind the scenes of one of the most unique — and heartwarming — challenges we’ve ever taken on: riding “it’s a small world” at Magic Kingdom for 10 straight hours to raise money for the Dream Team Project, which supports Make-A-Wish. That’s right — boat after boat, loop after loop, song after song — all for a cause that’s close to our hearts.We share what inspired us to take on this seemingly never-ending voyage, how the idea came to life, and why giving back through the Main Street 16 Challenge Weekend has become such an important part of what we do. You’ll hear the highs, the unexpected moments of hilarity, the not-so-magical parts, and the emotional impact of seeing our community come together to support something bigger than all of us.Throughout the day, we were joined by incredible friends, fellow Disney fans, and Main Street Magic listeners who hopped into boats with us — whether for one loop or several — and helped turn this challenge into a celebration of connection, kindness, and of course… a little bit of madness. We also cover how this event ties into the larger Main Street 16 Challenge Weekend, including race day fun, the scavenger hunt through Disney Springs, and our continued mission to support the Dream Team Project.Whether you love the ride or dread the tune, this episode is packed with magic, meaning, and memories. Tune in for the full recap and find out just how many loops we survived (spoiler: a lot).Main Street 16 Challenge Weekend is coming! May 15th – May 18th, 2025 in Walt Disney WorldThis event is a way to bring our community together and rally to raise money for a great cause. Part social gathering, part scavenger hunt, part ride challenge, Main Street 16 is a combination of all the things we love about the Disney Parks—The rides, the details, and most importantly, the people. And this event is about giving back to extraordinary people.BENEFITING THE DREAM TEAM PROJECTThe funds raised during the Main Street 16 Challenge Weekend benefit the Dream Team Project, an initiative founded by Lou Mongello of WDW Radio. This project collaborates with the Make-A-Wish Foundation to grant Disney-related wishes to children with life-threatening medical conditions, providing them and their families with memorable experiences at Walt Disney World.   Learn more and donate at MainStreet16.comMEI-Travel – Expertise. Ease. Value.No matter where you want to go, our trusted partner MEI-Travel, will handle the planning so you can focus on the memories. They offer free vacation planning services and have nearly 20 years of experience creating memorable vacations. Visit MEI-Travel for a fee-free, no-obligation quote today!Follow Us on Social MediaFacebook GroupFacebook: @MainStMagicTwitter: @MainStMagicTikTok: @MSMPodcastInstagram: @MainStMagicVisit Us Onlinewww.MainStMagic.comwww.MainStreetShirts.comGet Dining Alerts!Find last-minute and hard-to-find Disney dining reservations with MouseDining.com! Get text and email alerts when popular theme park dining reservations open up. Get last-minute seating! Get the next table! Set your alerts now! Get the next reservation!Visit our Partnerswww.MSMFriends.comThanks to TFresh Productions for our theme song 🎉 Plan Your Next Adventure with MEI-TravelLet the magic start before your trip even begins! Our trusted partner, MEI-Travel, takes the stress out of planning with nearly 20 years of expert service and completely free vacation planning. Whether it’s Walt Disney World, Disneyland, a cruise, or beyond—they’ve got you covered. Get your fee-free, no-obligation quote at MainStMagic.com/Travel and let the memories begin!📱 Stay Connected with Main Street MagicJoin the conversation and follow along for park tips, laughs, and magic:Facebook Group – Main Street Magic CommunityFacebook: @MainStMagicInstagram: @MainStMagicTikTok: @MSMPodcastX (formerly Twitter): @MainStMagic🌐 Visit Us OnlinePodcast & Blog: www.MainStMagic.comDisney-Inspired Apparel: www.MainStreetShirts.com🍽️ Snag That Hard-to-Get Disney Dining ReservationNever miss your dream meal again! Set up free alerts at MouseDining.com and get text or email notifications when reservations open up. Be the first to the table—literally!🤝 Support & Discover Our FriendsExplore more of our favorite resources, creators, and small businesses at www.mainstmagic.com/msm-friends/🎵 Theme Music Provided by TFresh ProductionsBecause every great show deserves a great beat.

We take you behind the scenes of one of the most unique — and heartwarming — challenges we’ve ever taken on: riding “it’s a small world” at Magic Kingdom for 10 straight hours to raise money for the Dream Team Project, which supports Make-A-Wish. That’s right — boat after boat, loop after loop, song after song — all for a cause that’s close to our hearts. We share what inspired us to take on this seemingly never-ending voyage, how the idea came to life, and why giving back through the Main Street 16 Challenge Weekend has become such an important part of what we do. You’ll hear the highs, the unexpected moments of hilarity, the not-so-magical parts, and the emotional impact of seeing our community come together to support something bigger than all of us. Throughout the day, we were joined by incredible friends, fellow Disney fans, and Main Street Magic listeners who hopped into boats with us — whether for one loop or several — and helped turn this challenge into a celebration of connection, kindness, and of course… a little bit of madness. We also cover how this event ties into the larger Main Street 16 Challenge Weekend, including race day fun, the scavenger hunt through Disney Springs, and our continued mission to support the Dream Team Project. Whether you love the ride or dread the tune, this episode is packed with magic, meaning, and memories. Tune in for the full recap and find out just how many loops we survived (spoiler: a lot).

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764: The Happiest Challenge That Ever Sailed: 10 Hours on “it’s a small world”

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This episode is 36 minutes long.

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This episode was published on April 18, 2025.

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We take you behind the scenes of one of the most unique — and heartwarming — challenges we’ve ever taken on: riding “it’s a small world” at Magic Kingdom for 10 straight hours to raise money for the Dream Team Project, which supports Make-A-Wish....

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