Jessie’s Roundup has officially opened at the Diamond Horseshoe in Magic Kingdom, arriving ahead of the official Cool Kids’ Summer start date of May 26, 2026. The Toy Story-themed activation runs through September 8, 2026, giving families a full summer of games, dancing, and yodeling alongside some of Andy’s favorite characters.
Jessie’s Roundup Brings Toy Story to Magic Kingdom’s Diamond Horseshoe for Summer 2026
In This Article
- What Jessie’s Roundup is and where to find it
- Characters and activities included in the experience
- When the activation runs and how long it lasts
- What the Diamond Horseshoe space looks like during the overlay
- Tips for visiting Jessie’s Roundup this summer
What Is Jessie’s Roundup?
Jessie’s Roundup is a limited-time interactive activation taking over the Diamond Horseshoe at Magic Kingdom. As we reported when Disney announced the experience, the tables have been cleared to make room for kids to run around in the air-conditioned space, surrounded by characters and theming from the Toy Story franchise.
The experience features games, dancing, and yodeling, described by Disney as a “high-spirited Western revue.” Jessie, Woody, and friends serve as the hosts for the rootin’ tootin’ fun.
When Does It Run?
Jessie’s Roundup was originally slated to begin May 26, 2026, as part of the broader Cool Kids’ Summer programming across Walt Disney World. The experience opened early today, May 24, running through September 8, 2026.
What’s Inside
The Diamond Horseshoe has received a light Toy Story overlay for the activation. The experience is built around two distinct show moments, each featuring characters and live performers in an interactive format designed for younger guests. Around the perimeter of the room, a handful of western-themed games keep kids busy between shows. The air-conditioned space makes it a welcome stop during the Florida summer heat.
Games
The games along the perimeter are first-come, first-served, with no tickets or reservations required. We spotted four options: upright horseshoes (a ring toss variation), a throwing game similar to cornhole, a visual maze to complete, and a spot-the-differences game featuring 10 differences to find.
Show Moment: Sing-Along with Dusty Strings and Bullseye
The first show moment centers on a sing-along led by Dusty Strings, a guitarist performer, joined by Bullseye. Guests are invited to participate alongside the beloved Toy Story horse in what sets up as a warm, musical kickoff to the experience.
Show Moment: Dancing and Yodeling Contest with Jessie and Woody
The second show moment brings Jessie and Woody to the stage for a dancing and yodeling contest. They’re joined by a jump rope crew, who perform a routine on stage before taking the action to the dance floor, jumping rope with young guests who’ve been deputized as Jr. Deputies for the occasion. It’s the high-energy centerpiece of the experience and the moment most kids will remember.
How It Works
Each show moment runs about 10 minutes, with roughly 10 minutes between them. There’s no queue to enter, guests simply walk in and out of the Diamond Horseshoe as they please. That makes it easy to pop in, catch a show moment, and move on, or stay for both if the kids are into it.
Part of Cool Kids’ Summer
Jessie’s Roundup is one of several new activations debuting across Walt Disney World as part of Cool Kids’ Summer. Other offerings opening May 26 include Bluey’s Wild World at Animal Kingdom, Soarin’ Across America at EPCOT, and a Muppets takeover of Rock ‘n’ Roller Coaster at Hollywood Studios. But at Magic Kingdom, Jessie’s Roundup is the headlining new experience for the season.
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