Magic Kingdom is bringing the Wild West back to the Diamond Horseshoe stage. Woody and Jessie have debuted fresh new accessories tied to Toy Story 5, which hits theaters on June 19, 2026. The new looks are part of Walt Disney World’s Cool Kids’ Summer initiative and are now live at the park.
New Character Accessories Tied To Toy Story 5
The cowboy duo’s updated looks are the first major character refresh for the Toy Story trio in years. Jessie now proudly wears the sheriff’s badge that Woody gave her at the end of Toy Story 4. Woody sports a red bandana poncho. Buzz Lightyear has also joined the accessories update, with a shiny star sticker on his spacesuit. These additions connect the park experience directly to the upcoming film’s storyline.
Jessie’s Roundup Returns Live Entertainment To The Diamond Horseshoe
Jessie’s Roundup: A Rip-Roarin’ Revue debuted on May 26, 2026, at the Diamond Horseshoe in Frontierland. It marks the venue’s return to live entertainment for the first time in over two decades. The interactive experience transforms the historic space into a high-energy western celebration. Families can craft, dance, and yodel alongside Jessie, Woody, and Bullseye. A live cast member with a guitar leads the musical festivities, and both Jessie and Woody have speaking roles throughout the show.
What This Means For Disney Parks Fans
Jessie’s Roundup runs through September 8, 2026. The Diamond Horseshoe temporarily paused its table-service dining on May 16 to prepare for the activation. Regular dining service is expected to return in fall 2026. The show is part of Disney’s broader push toward more interactive, immersive character experiences. Cool Kids’ Summer also includes GoofyCore at EPCOT, Bluey’s Wild World at Animal Kingdom, and Mickey Mouse Clubhouse Live at Hollywood Studios.
For Toy Story fans, the timing could not be better. Toy Story 5 explores what happens when Bonnie becomes obsessed with a tablet named Lilypad, and the park experience gives families a chance to engage with these characters in a setting that celebrates their classic Western roots. For more on what is new at Walt Disney World this summer, check out our guide to everything new at Hollywood Studios. For official details on Jessie’s Roundup, visit the Walt Disney World website.
