I previewed “Jessie’s Roundup” coming to Magic Kingdom and it feels built for summer crowds
Disney previewed the new “Jessie’s Roundup” show coming to Frontierland as part of “Cool Kids’ Summer” at Magic Kingdom Park, and after getting an early look during a media preview at World Showplace in Epcot, it feels purpose-built for busy summer days at Magic Kingdom.
Originally scheduled to debut May 26, 2026, inside Diamond Horseshoe, the interactive entertainment offering opened ahead of schedule this weekend and brings live energy back to a space that hasn’t regularly hosted this type of entertainment experience in years.

The media preview gave us a sample of what to expect from the full production of ‘Jessie’s Roundup: A Rip-Roarin’ Revue!’ (what a mouthful). And before we even had a chance to compile our thoughts and get an article together, Disney quietly premiered the experience today at Magic Kingdom, two days ahead of schedule.
“Jessie’s roundup” features a brand-new original song
According to show director Matthew Hamel, the new show was designed to combine music, gameplay, rope tricks, and audience interaction inside the historic Frontierland venue.
“We’re gonna see rope tricks and music and gameplay, all that kind of stuff,” Hamel said. “We’re actually also premiering a brand new song.” The show also includes a rendition of “You’ve Got a Friend in Me” performed by Woody and Jessie.
New “Toy Story 5” details appear in the show
The experience also includes updated character details tied to the upcoming “Toy Story 5.” Woody appears wearing his new bandana cape, while Jessie sports her sheriff’s badge from the upcoming film. The show also includes a playful joke about Woody’s age, which aligns with some of the jokes shown in trailers for the movie.
This new interactive show adds to the lineup of Toy Story experiences at Walt Disney World.

Photo by Dani Meyering
Disney wanted families to interact with each other, not just the characters
Hamel said one of the biggest creative goals behind “Jessie’s Roundup” was finding the right balance between live character interaction and family participation.
“It’s been a really fun process, actually,” Hamel said. “The team has been putting together, trying to find the perfect formula of how much our guests get to interact with the characters, but also get to interact with each other and play and sing as a family.”
Hamel said those shared experiences are a major part of what Disney Live Entertainment hopes families take away from the show.
“Those types of things are kind of what the core memories that we like to build off of,” he said.

That interactive element continues one of the biggest strengths of Disney’s “Cool Kids’ Summer” initiative — giving children opportunities to move, dance, and engage directly with characters during a part of the day when many families are looking for a break from the Florida heat and long attraction waits.
WATCH: Our video below shows the new “Horseshoe Stomp” song as performed by the ‘Jessie’s Roundup’ crew, and a short interview with the show director.
Diamond Horseshoe finally feels alive again
One of the smartest parts of “Jessie’s Roundup” may simply be where Disney chose to put it. In the middle of a Florida summer, an indoor interactive show inside Frontierland’s Diamond Horeshoe gives families a chance to cool off without slowing down the energy level for younger kids.
It also gives children an opportunity to move their bodies, sing, dance, and actively participate instead of standing in long queues during one of the busiest times of the year.

Photo by Dani Meyering
I’ll be visiting Magic Kingdom later this week to experience the offering in its full in-park setting, but based on this preview alone, “Jessie’s Roundup” already feels like a natural fit for Frontierland and a meaningful way to breathe new life into Diamond Horseshoe.
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