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 World

This 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 PROJECT
The 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.com

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Thanks to TFresh Productions for our theme song

764: The Happiest Challenge That Ever Sailed: 10 Hours on “it’s a small world” 36:34 Share

Main Street Magic - A Walt Disney World Podcast

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