‘Toy Story’ coming to Frontierland in Magic Kingdom
Jessie’s Roundup will open in Frontierland at Magic Kingdom just in time for “Toy Story 5.”
Photo by Blake Taylor
Jessie’s Roundup will take place inside the Diamond Horseshoe venue from May 26 – Sept. 8, 2026, as part of Walt Disney World’s Cool Kids’ Summer campaign.
Originally published December 2025, updated April 2026 by Dani Meyering
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!)
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.
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.
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.
New: Disney Pixar’s Toy Story Western Collection merchandise
Arriving at Magic Kingdom is a new merchandise collection featuring Woody and Jessie with a detailed Western motif.
At the center of the lineup is a denim vest featuring embroidered patches of Woody and Jessie, stitched onto a soft, medium-wash fabric. The vest has a slightly structured fit with button-front detailing, giving it that classic frontier look while still feeling lightweight enough for a theme park day. Underneath, it’s styled with a cream-colored graphic tee covered in sketch-style western scenes with cacti, desert landscapes, and subtle character line art.
The standout tee in the collection is the “Dry Gulch Rodeo” ringer shirt, designed to look like a vintage event poster. It features bold, retro typography and artwork of Woody riding Bullseye, with smaller nods to Jessie, Stinky Pete, and Bullseye written into the “starring” lineup. Red trim at the collar and sleeves completes the throwback aesthetic.
Accessories continue the rodeo theme, including a pair of Jessie-inspired Minnie ears made with mixed materials—soft fabric ears, cow-print accents, rope detailing, and a miniature red cowgirl hat perched on top.
Additional items in the collection include graphic mugs with western-style illustrations, a quilted throw featuring patchwork panels with character embroidery (notably Jessie and Bullseye), and a sleeveless denim shirt with a subtle embroidered character patch.
Photos by Matt Roseboom
Overall, this collection feels like a wearable extension of “Woody’s Roundup,” which is exactly what we expect from the ‘Jessie’s Roundup’ experience coming to Frontierland this summer.
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