Credit: DisneyMagic Kingdom’s Diamond Horseshoe is getting a complete transformation for summer 2026, and it’s bringing some unexpected character experiences to Liberty Square. Disney announced today that Jessie’s Roundup will take over the historic venue as part of the Cool Kids’ Summer activation running from May 26 through September 8, 2026.
This represents a significant shift for the Diamond Horseshoe space, which has seen various iterations over the years but hasn’t hosted a dedicated character experience like this before. For Toy Story fans and families with young children, this creates an entirely new reason to venture into the often-overlooked corner of Magic Kingdom where the Diamond Horseshoe resides.
The concept behind Jessie’s Roundup sounds like organized chaos in the best possible way. Disney is clearing out the tables from the Diamond Horseshoe’s interior, transforming the space into an activity center where kids can run around freely in an air-conditioned environment.
Jessie will lead the experience alongside Woody and other Toy Story characters, offering crafts, dancing, and yes, yodeling activities in what Disney is calling a “western revue.” The rootin’ tootin’ theme fits perfectly with the Diamond Horseshoe’s existing Old West saloon aesthetic, creating a natural connection between the venue’s historical theming and the Toy Story franchise’s frontier elements.
What makes this particularly interesting is that these Toy Story characters don’t typically meet at Magic Kingdom. While you can find Woody, Jessie, and Buzz Lightyear at Hollywood Studios in various locations, Magic Kingdom hasn’t been a regular home for Toy Story character interactions.
This activation brings them into the park specifically for the summer season, filling a character gap and giving families another air-conditioned activity option during Florida’s most intense heat. The limited-time nature of the experience through September 8 means this is truly a summer exclusive rather than a permanent addition to the park’s lineup.
What to Expect at Jessie’s Roundup
Based on Disney’s description, Jessie’s Roundup appears to be an interactive play experience rather than a traditional character dining meal or standard meet-and-greet. The emphasis on crafts, dancing, and yodeling suggests structured activities led by cast members with Toy Story characters making appearances throughout.
Think of it as a character dance party meets craft session meets Old West entertainment revue, all rolled into one energetic package designed to burn off kid energy while parents enjoy the air conditioning.
The clearing of tables from the Diamond Horseshoe is significant because it signals this isn’t a dining experience but rather a dedicated play space. Families won’t be sitting down for a meal with characters at their tables. Instead, kids will have room to move around, participate in activities, and interact with characters in a more free-form environment.
This approach differs from character dining experiences at other locations like Chef Mickey’s or Topolino’s Terrace, where the structure revolves around a meal service with character visits to each table.
The yodeling element is a fun callback to Jessie’s character in the Toy Story films, where her yodel has been a signature trait since Toy Story 2. Whether Disney will actually teach kids to yodel or simply incorporate yodeling into the entertainment remains to be seen, but it’s the kind of quirky detail that makes this feel like a genuine Toy Story experience rather than just throwing characters into a generic space.
The western revue description suggests some kind of show or performance element, possibly with Jessie and Woody leading line dances, teaching western-themed songs, or putting on short entertainment segments between craft activities. This combination of structured entertainment and hands-on activities should keep kids engaged for a reasonable amount of time while giving parents a break from the intensity of touring the parks in summer heat.
Part of Cool Kids’ Summer 2026
Jessie’s Roundup is just one component of Disney World’s broader Cool Kids’ Summer initiative, which runs from May 26 through September 8, 2026. This seasonal programming package includes multiple new experiences, enhanced character appearances, and various deals designed to attract families during the traditionally hot summer months when crowd levels can fluctuate.
The package offerings include some significant value propositions for families. Disney is offering two free room nights and theme park days when you purchase a 4-night, 4-day room and ticket package through Walt Disney Travel Company.
This essentially gives you six days at Disney World for the price of four, applying to stays most nights from May 26 through September 15, 2026. The booking window opens January 6, 2026 and runs through February 15, 2026.
Hotel discounts reach up to 30% on select Disney Resort hotels for stays most nights from May 1 through October 4, 2026. Florida Residents can save up to 35%, while Annual Passholders get up to 40% off rooms at select properties. These discounts make summer visits more affordable despite the heat and humidity that defines Florida summers.
A particularly appealing perk for resort guests is free water park access on check-in day. Guests staying at Disney Resorts Collection hotels between May 26 and September 8 receive complimentary admission to either Typhoon Lagoon or Blizzard Beach on their arrival day. Both water parks will operate during Cool Kids’ Summer, giving families an immediate option to cool off after checking in.
The free dining plan for children ages 3 to 9 when adults purchase a package with a dining plan adds another layer of value. This applies to packages that include a room at a Disney Resort hotel and a dining plan for guests ages 10 and up, potentially saving families hundreds of dollars on meals throughout their vacation.
Other Cool Kids’ Summer Experiences
Beyond Jessie’s Roundup, Cool Kids’ Summer brings several new character experiences and attraction updates across Walt Disney World.
Bluey and Bingo are coming to Animal Kingdom’s Conservation Station starting summer 2026. Guests can play games from Bluey episodes, take photos with the characters, and see animals native to Australia after riding the Wildlife Express Train. This marks a significant character addition for Animal Kingdom, which has fewer character experiences compared to Magic Kingdom and Hollywood Studios.
EPCOT’s CommuniCore Hall will host GoofyCore, where Goofy leads activities including Goofy’s Game Machine with games like Goofy Says, Balloon Bonanza, and Parachutes ‘n’ Pipsqueaks. DJ Dance Pants and other Goof Troop characters will appear, giving EPCOT a more robust character presence during the summer months.
Hollywood Studios debuts a new Mickey Mouse Clubhouse Live stage show where Mickey and Minnie search for their friends in an interactive production with original songs. This gives younger Disney Jr. fans a dedicated show experience at the park.
Several attractions are receiving updates or overlays for summer 2026. Buzz Lightyear’s Space Ranger Spin at Magic Kingdom gets new handheld blasters and updated ride vehicles. Millennium Falcon: Smugglers Run at Hollywood Studios introduces a new mission featuring Din Djarin and Grogu starting May 22, marking the first time guests choose which planets their ship visits during the ride. Rock ‘n’ Roller Coaster reopens with The Muppets and Electric Mayhem replacing Aerosmith. EPCOT’s Soarin’ debuts Soarin’ Across America celebrating the nation’s 250th birthday, opening by Memorial Day.
Disney Resorts Collection hotel guests receive 30-minute early theme park entry, and during Cool Kids’ Summer, characters will appear across all four parks during this early entry period. Select resorts including Pop Century, Art of Animation, Caribbean Beach, and Port Orleans Riverside will offer additional family experiences with scheduled character visits during summer 2026.
Planning Your Visit
If Jessie’s Roundup and the broader Cool Kids’ Summer programming appeal to your family, booking during the January 6 through February 15 window makes sense to lock in the package deals. The combination of free nights, free dining for kids, and free water park access on check-in day creates substantial value, potentially offsetting some of the challenges that come with visiting Disney World during peak summer heat.
The Diamond Horseshoe location in Liberty Square means Jessie’s Roundup provides an air-conditioned break option in an area of Magic Kingdom that doesn’t have many indoor attractions. Families can escape the afternoon heat, let kids burn energy in a controlled environment, and experience character interactions that aren’t available elsewhere in the park.
Whether Jessie’s Roundup becomes a permanent addition after summer 2026 or remains a seasonal offering depends on guest response and Disney’s plans for the Diamond Horseshoe space going forward. For now, it represents a creative use of an underutilized venue and brings Toy Story characters to Magic Kingdom in a meaningful way.
What do you think about Disney bringing Toy Story characters to Magic Kingdom’s Diamond Horseshoe? Are you planning to check out Jessie’s Roundup during your summer visit, or are you more interested in some of the other Cool Kids’ Summer offerings like Bluey at Animal Kingdom or the Muppets on Rock ‘n’ Roller Coaster? Drop a comment and let us know which summer experience you’re most excited about!