2026 is shaping up to be an interesting year at Walt Disney World. Construction projects, refurbishments, and new takes on old favorites abound. However, perhaps the most interesting may be the resurrection of one of the Magic Kingdom’s oldest restaurants in a stunning way.
As part of Disney’s Cool Kids Summer promotion, a new Toy Story-themed character experience is coming to the Magic Kingdom’s Frontierland. According to Disney, Jessie’s Roundup will be led by “everyone’s favorite yodelin’ cowgirl” Jessie, who will help guests “craft, dance and yodel their day away” with Woody and friends in a “high-spirited Western revue!” The most notable aspect of the show to longtime Disney fans, however, is where it’s being staged: The Diamond Horseshoe, a legendary — and for the last few decades legendarily underutilized — space at Disney World.
The Diamond Horseshoe Review was an opening day attraction at Walt Disney World, serving as the East Coast counterpart to Disneyland’s legendary Golden Horseshoe Saloon Review. Iconic Disneyland performer Wally Boag helped develop the show, which featured live music, sing-along songs, and appearances from Slue Foot Sue and Pecos Bill, along with a table service meal.
The show ran for 15 years before being significantly reworked in 1986. The new version — the Diamond Horseshoe Jamboree — was notable for being the first Disney World dining experience that required advanced reservations, which could be booked on Main Street after rope drop each morning.
The Jamboree version of the shoe ran for about a decade until the mid-90s, when the shoe was once again reworked, and — arguably more importantly — the restaurant changed to a quick service menu, and guests could simply waltz in and out as the show was performed. This change was notably intertwined with a period of cost-cutting across Disney’s parks following the initial financial failure of EuroDisney AKA Disneyland Paris.
This version existed until 2003, when the show ended and was replaced by Goofy’s Country Dancin’ Jamboree. That show was, um, not well received, and ran for just about a year before being replaced by… nothing.
The Diamond Horseshoe sat unused for the rest of the decade before being transitioned back into a quick-service dining location, though this time lacking any entertainment outside of a player piano.
Later in the decade, the restaurant transitioned once again, this time to its current form as a table service restaurant serving the same all-you-care-to-enjoy menu as its neighbor, The Liberty Tree Tavern.
All of which brings us back to Jessie’s Roundup. Disney has yet to confirm exactly if the offering is going to be a character meal, a show, or simply a character experience, though given the complicated history of the Diamond Horseshoe, we wouldn’t be surprised at any of those outcomes. Stay tuned to AllEars for more on Disney World’s history.
The Ridiculously Detailed History of Disney World’s Frontierland
Which version or versions of the Diamond horseshoe have you experienced? Let us know in the comments below.
Leave it to modern Day Disney to make a literally Toy Story themed restaurant at Hollywood Studios and have it NOT be character dining. Only to take a restaurant that most seem to just walk right by in Magic Kingdom and make it a…wait for it… TOY STORY CHARACTER DINING restaurant. LOL!