Yee Haw! Get a First Look at Jessie’s Roundup Coming to Walt Disney World’s Cool Kids' Summer

We have our first look at the Toy Story takeover of the Diamond Horseshoe as Jessie’s Roundup gets ready to join Walt Disney World’s 2026 Cool Kids' Summer.

What’s Happening:

• Following the popularity of last year’s Cool Kids' Summer celebration at Walt Disney World, the event is officially making a comeback for summer 2026.
• Alongside the return of several fan-favorite experiences, guests can also expect brand-new entertainment offerings this year, including an exciting update coming to Liberty Square at Magic Kingdom.

• As part of the Cool Kids’ Summer festivities, Toy Story characters will take over the Diamond Horseshoe for a lively western-themed party. 
• Guests can team up with Woody, Jessie, and their pals during Jessie’s Roundup, an interactive show filled with dancing, crafts, music, and plenty of high-energy fun.
• Just ahead of the event's return, Disney shared a first look at the fun coming to the inside of Diamond Horseshoe. 

• Decked out with Jessie’s Roundup decor, you’ll be able to meet your favorite characters in their updated costumes that were also revealed today!
• The party will include tons of games and dancing, so don’t miss out on Jessie’s Roundup!

• The new experience will join several returning and debuting entertainment options across the parks, including the comeback of GoofyCore at EPCOT, the arrival of Bluey at Disney’s Animal Kingdom’s Conservation Station, and Disney Jr. Mickey Mouse Clubhouse Live! at Disney’s Hollywood Studios.
• Cool Kids' Summer will run at Walt Disney World from May 26 through September 8, 2026.
• For those looking for help planning their next magical adventure, Laughing Place recommends Mouse Fan Travel.
• Plus, don’t miss Toy Story 5 when it hits theaters June 19th!

Read More Walt Disney World:

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• Exceeding Expectations: Do Dual Short-Turnaround Successes Mark a New Direction for Imagineering? 
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