Walt Disney World® has announced an exciting addition to Magic Kingdom entertainment: Jessie’s Roundup, a brand-new live show debuting at the historic Diamond Horseshoe in Liberty Square. The interactive western revue will mark the first live show at the Diamond Horseshoe in more than 20 years, making it a major milestone for Disney fans.
The show will debut as part of Cool Kids’ Summer at Walt Disney World, featuring beloved characters from Toy Story, including Jessie and Woody. Additional details and performance times will be announced at a later date.
“The Diamond Horseshoe is one of Magic Kingdom’s most iconic venues,” said Natali Bohm, Owner of Axis Travel Group. “Bringing live entertainment back after two decades—especially with Toy Story characters—is a huge win for families visiting Walt Disney World.”
What Is Jessie’s Roundup at Magic Kingdom?
Jessie’s Roundup is an interactive, family-friendly western revue that invites guests to craft, dance, sing, and yodel along with Toy Story pals. Designed especially for younger guests, the show offers a break from traditional rides while still delivering Disney storytelling and fun.
Located in Liberty Square at Magic Kingdom, the Diamond Horseshoe provides an air-conditioned, indoor entertainment option—ideal for summer visits.
“Shows like this are incredibly valuable during peak travel seasons,” Bohm explained. “They give families a chance to cool off, recharge, and enjoy something different from rides.”
A Look at the Diamond Horseshoe’s History
The Diamond Horseshoe has been part of Magic Kingdom since opening day, originally debuting as the Diamond Horseshoe Revue. Its most recent live production, Goofy’s Country Dancin’ Jamboree, ran from 2003 to 2005.
Since the park’s reopening after COVID, the Diamond Horseshoe has primarily served as overflow seating for Liberty Tree Tavern, offering the same menu due to a shared kitchen. Prior to that, the location featured Frontierland-style barbecue, including brisket, pulled pork, sausage, and classic sides.
“The return of live entertainment could signal a bigger shift for this space,” Bohm noted. “Disney doesn’t revive a historic venue like this without long-term plans.”
Part of Cool Kids’ Summer at Walt Disney World
Jessie’s Roundup is one of several offerings debuting during Cool Kids’ Summer, Disney’s seasonal celebration featuring limited-time entertainment, activities, and experiences throughout Walt Disney World Resort.
“This kind of seasonal entertainment is exactly why timing matters when planning a Disney vacation,” Bohm said. “We help our clients travel when the parks are offering the most value and variety.”
Why Book Your Disney Vacation with Axis Travel Group?
Axis Travel Group specializes in Disney destinations and is proud to be a Disney EarMarked Gold Agency, a designation awarded by Disney to agencies with proven expertise and exceptional guest service.
“Disney vacations involve constant changes—from entertainment schedules to dining options,” said Bohm. “Our role is to make sure clients don’t miss new experiences like Jessie’s Roundup.”
Benefits of Booking with a Disney Travel Agent
When you book your Walt Disney World vacation with Axis Travel Group, you receive:
Expert Disney vacation planning
Personalized park strategies based on new shows and attractions
Monitoring of Disney announcements and seasonal offerings
One-on-one support before, during, and after travel
Planning a Walt Disney World Vacation in 2026?
With Jessie’s Roundup, Cool Kids’ Summer, and the return of live entertainment to the Diamond Horseshoe, summer 2026 is shaping up to be an exciting time to visit Magic Kingdom.
Don’t Wait—Book Your Disney Vacation Today!