Disney recently announced that Jessie’s Roundup will take over the Diamond Horseshoe in Magic Kingdom this summer. This new experience anchors the “Cool Kids’ Summer” activation across the resort. It marks a significant shift for the Liberty Square venue, which typically serves as an overflow dining hall. Fans of Toy Story can enjoy this high-energy “western revue” starting May 26, 2026.
What to Expect at Jessie’s Roundup
The experience features Jessie, Woody, and other favorite pals from the Toy Story franchise. Disney describes the event as a “rootin’ tootin’ good time” filled with interactive crafting, dancing, and yodeling. Unlike traditional character dining, this functions as an interactive play experience. Reports indicate Disney will clear out the dining tables to transform the interior into an activity center.
This “western revue” allows children to burn off energy in a fully air-conditioned environment. The Old West saloon aesthetic of the Diamond Horseshoe provides a natural fit for the Toy Story frontier theme. While a player piano currently occupies the stage, the new show brings live entertainment back to the space for the first time in years.
Important Dates and Planning Details
Jessie’s Roundup will run for a limited time from May 26 through September 8, 2026. The experience remains included with regular park admission and does not require a separate ticket. This summer activation also coincides with major vacation deals launching on January 6, 2026. These offers include a “4-night, 4-day” package that provides two additional free nights and park days.
It remains unclear if the Diamond Horseshoe will continue its traditional Thanksgiving-style dining service during the summer. Currently, the restaurant acts as an overflow for the neighboring Liberty Tree Tavern. However, reservations for the venue are only available through March 2026. This gap suggests a total transformation of the space will occur before the summer kickoff.
Cool Kids’ Summer Highlights
Jessie’s Roundup joins a wider lineup of seasonal entertainment across Walt Disney World. Other highlights include the debut of Bluey and Bingo at Animal Kingdom and GoofyCore at EPCOT. Families staying at select Disney resorts also enjoy enhanced character appearances during Early Theme Park Entry.
The “Cool Kids’ Summer” initiative provides extra value for families visiting during the hotter months. Between free water park admission on check-in day and new character experiences, summer 2026 is a major season for the resort.
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