Jessie’s Roundup to Bring Live Entertainment Back to the Diamond Horseshoe for the First Time in 20 Years

Jessie’s Roundup to Bring Live Entertainment Back to the Diamond Horseshoe

The curtains are finally rising again in Frontierland! For the first time in over two decades, the Diamond Horseshoe at Magic Kingdom will host a full-scale stage production. Titled Jessie’s Roundup, this new western revue is set to debut as part of the “Cool Kids’ Summer” celebration in 2026.

A Rootin’ Tootin’ New Show

Starting May 26, 2026, the Diamond Horseshoe will transform into a high-energy activity center led by everyone’s favorite yodeling cowgirl. Guests can join Jessie, Woody, and their Toy Story pals for an interactive experience described as a mix of a “western revue” and a family play-along.

Related-Magic Kingdom’s Diamond Horseshoe opening in September

According to Disney, the experience will allow kids and families to:

• Craft custom western-themed souvenirs.
• Dance along with Toy Story characters to country-inspired tunes.
• Yodel their hearts out in a nod to Jessie’s signature talent.

This activation provides a much-needed air-conditioned retreat for families during the peak Florida summer heat. The event is scheduled to run through September 8, 2026.

Related-Toy Story Land Kiosk Nearing Completion at Hollywood Studios

Ending a 20-Year Hiatus

The announcement marks a historic moment for the Diamond Horseshoe, which has largely served as a seasonal dining hall or a quiet player-piano lounge for the last twenty years.

The last time the venue hosted a structured show was Goofy’s Country Dancin’ Jamboree, which ran from 2003 to 2005. Before that, the venue was home to the legendary Diamond Horseshoe Revue, an opening-day attraction that featured can-can dancers and variety acts from 1971 until its closure in early 2003.

Part of “Cool Kids’ Summer”

Jessie’s Roundup is just one piece of a massive summer campaign at Walt Disney World. Other highlights for the 2026 season include:

• Bluey and Bingo arriving at Disney’s Animal Kingdom.
• GoofyCore at EPCOT’s CommuniCore Hall.
• Mickey Mouse Clubhouse Live! at Disney’s Hollywood Studios.

While further details on showtimes and potential dining components for Jessie’s Roundup have yet to be revealed, fans are already celebrating the return of live performance to one of the park’s most historic stages.

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