We spent 40 minutes at Jessie’s Roundup in Magic Kingdom and it was a hit
Jessie’s Roundup has officially joined Walt Disney World’s Cool Kid Summer lineup, bringing live entertainment, Toy Story characters, interactive games, and indoor activities to Magic Kingdom.
Jessie’s Roundup has rolled into the Diamond Horseshoe venue from May 26 – Sept. 8, 2026, as part of Walt Disney World’s Cool Kids’ Summer campaign.
While Disney initially promoted the live entertainment component, my son and I found the interactive games and play opportunities to be just as much of the draw during a recent visit.
Originally published in January 2026 by Blake Taylor, most recently updated by Dani Meyering on May 30, 2026.
Jessie arrives in Magic Kingdom
Disney announced Jessie’s Roundup on Jan. 5 by saying:
Just for Cool Kids’ Summer, pals from “Toy Story” are ready for a rootin’ tootin’ good time at the Diamond Horseshoe at Magic Kingdom. Join Jessie, Woody, and friends for some energetic fun at ‘Jessie’s Roundup,’ where you’ll craft, dance, and yodel your hearts out in this western revue.
Photo by Blake Taylor
Disney debuted the Cool Kids’ Summer initiative in 2025 with character-based activations at all four parks.
The Jessie’s Roundup experience coincides with the release of “Toy Story 5,” which debuts in theaters on June 19. (We got to see the first five minutes of “Toy Story 5”; read our previous coverage for our description of what we saw!)
Jessie’s Roundup is open daily 9:30 a.m. – 6 p.m.
Diamond Horseshoe has been utilized as a flex space for dining and entertainment over the decades. For years, it was home to the old-fashioned Diamond Horseshoe Revue. The space currently functions as a table-service restaurant with all-you-care-to-enjoy American meals, sharing a menu with Liberty Tree Tavern next door.
Photo courtesy of Disney
In other character-related news, Disney friends will greet guests during Early Theme Park Entry at all four Walt Disney World theme parks as part of Cool Kids’ Summer. (This aligns with the roaming characters experiments we observed last summer.) Characters will also appear at Disney’s Pop Century Resort, Disney’s Art of Animation Resort, Disney’s Caribbean Beach Resort, and Disney’s Port Orleans Resort – Riverside for Cool Kids’ Summer celebrations.
Additionally, Cool Kids’ Summer includes Bluey arriving at Animal Kingdom, “Mickey Mouse Clubhouse Live!” opening at Hollywood Studios, and a slate of discounts.
Photo by Dani Meyering
Live entertainment featuring Woody, Jessie and Bullseye
During our visit, we arrived around 2:30 p.m. and caught the final few minutes of a performance featuring Woody and Jessie. The pair wrapped up a dance number called the “Horseshoe Stomp,” an original song created for the experience that feels especially fitting inside Diamond Horseshoe.
Photo by Dani Meyering
I had the pleasure of speaking with Michael Hamel, show director for Disney Live Entertainment, about this new song during a media preview of ‘Jessie’s Roundup.’
Later, at precisely 3:20 p.m., musician Dusty Strings took the stage with his guitar, opening the next set with “Hey Howdy Hey.” Bullseye soon joined the performance, followed by another round of the Horseshoe Stomp.
The show then expanded beyond the stage as performers entered the audience area and encouraged children to participate. Guests were invited to dance along as Dusty Strings performed “A Cowboy Needs a Horse,” the classic song from Disney’s 1956 animated short of the same name.
Photo by Dani Meyering
Quick note: Strollers are not allowed inside Diamond Horseshoe.
The games were the biggest surprise
The performances may get top billing, but the activity stations ended up being the highlight of our visit. Spread throughout Diamond Horseshoe were multiple Toy Story-themed games, including a horseshoe toss game, a spot-the-difference activity and other western-inspired activities designed for youngsters.
Photo by Dani Meyering
Having attended Cool Kids’ Summer offerings during the program’s inaugural year in 2025, I was surprised by how much more elaborate these activities felt compared to some of last year’s offerings at Storybook Circus.
The stations were thoughtfully themed, easy for kids to understand, and offered enough variety to keep children engaged between performances. Kids need activities like this to break up the demands of a busy theme park day.
A welcome break from the Florida heat
One of the most practical benefits of Jessie’s Roundup may be something Disney hasn’t emphasized very much: it’s indoors. Shortly after we arrived, Festival of Fantasy Parade stepped off just outside. Rather than heading out into the crowds, we stayed inside Diamond Horseshoe and continued exploring the activity stations.
The air-conditioned venue offered plenty of room for families to spread out, with seating available throughout the space and enough open floor area for children to move.
Photo by Dani Meyering
During a long day at Magic Kingdom, the combination of air conditioning, seating, entertainment, and relatively low-pressure activities creates an appealing break.
Jessie’s Roundup | The bigger picture for Frontierland
Jessie’s Roundup in summer 2026 won’t be the first time the “Toy Story” crew has found a home in Frontierland, or in the Diamond Horseshoe. In 2003, Jessie, Woody, and Bullseye co-starred in “Goofy’s Country Dancin’ Jamboree,” a live show inside the venue. A few years later, the characters led crowds outside in “Woody’s Cowboy Camp,” an audience participation show in the Frontierland street.
Although Diamond Horseshoe is technically located in Liberty Square, the Old West setting feels right at home alongside neighboring Frontierland attractions, especially when Woody and Jessie take over.
Photo by Dani Meyering
Frontierland at Magic Kingdom is in the middle of a sweeping transformation. Completed projects include ‘Tiana’s Bayou Adventure’ replacing Splash Mountain, as well as ‘Country Bear Musical Jamboree’ infusing modern Disney songs into the long-running animatronic bear show.
In-progress efforts include a major refurbishment of Big Thunder Mountain Railroad (which will reopen this spring after being closed for over a year) and ongoing construction for two “Cars”-themed rides, which replace the now-demolished Tom Sawyer Island and the Rivers of America.
Last summer, we spoke with Imagineers about their guiding principles for Frontierland’s transformation.
For families with younger children, especially those looking for a place to cool off and slow down for a little while, Jessie’s Roundup may end up being one of the most successful parts of Cool Kid Summer at Magic Kingdom.
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