Diamond Horseshoe hasn’t had a show in over 20 years, but that has changed with Jessie’s Roundup. It’s part of Cool Kids’ Summer at Walt Disney World to promote the release of Toy Story 5. The experience is set to officially debut on May 26, 2026, but we caught a preview on May 24th. There was no permanent signage outside of The Diamond Horseshoe for the show, just a...

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