Photos/Videos: Jessie's Roundup Takes Over the Diamond Horseshoe for Cool Kids' Summer

Toy Story has taken over 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 now experience 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.
• Laughing Place had the chance to check out Jessie’s Roundup as it debuted today, May 26th, for the kick off of Cool Kids’ Summer.
• Upon entering the Diamond Horseshoe, guests can get a nametag with their “deputy name” based on their favorite character. 

• The inside of the Frontierland location was decked out in adorable decor which was brought to life by character appearances, live music, and games! 

• Cast members also had some rootin’ tootin’ costumes for Jessie’s Roundup.

• Check out full performances of the two shows below:

• For those looking to head to the Most Magical Place on Earth, Laughing Place recommends Mouse Fan Travel.

Read More Walt Disney World:

• Photos: Fan-Favorite Characters Arrive at Walt Disney Studios Courtyard 
• Photos: New Walt Disney World X Bluey Merchandise Drops at Disney's Animal Kingdom 
• Photos/Video: Bluey's Wild World at Conservation Station Soft Opens at Disney's Animal Kingdom