Diamond Horseshoe Closing for Jessie’s Roundup: What You Need to Know

The Diamond Horseshoe at Magic Kingdom is closing its table service dining on May 16, 2026 — and it’s being transformed into Jessie’s Roundup, a Toy Story character experience running during Cool Kids’ Summer. If you want to eat at the Diamond Horseshoe before the switch, your window is closing. Here’s everything you need to know about the transition.

The Timeline

Table service dining at the Diamond Horseshoe ends May 16, 2026. Cool Kids’ Summer runs May 26 through September 8, so the restaurant closes nearly two weeks before the event starts — giving Disney time to fully transform the space. Dining is expected to resume in fall 2026 once Cool Kids’ Summer wraps. That’s roughly a four-month pause on the current restaurant experience.

What Is Jessie’s Roundup?

Jessie’s Roundup is a western-themed Toy Story character experience featuring Jessie, Woody, and other Toy Story characters. The experience includes crafts, dancing, and yodeling — it’s built as an interactive, family-friendly event that fits the western aesthetic of the Diamond Horseshoe’s Liberty Square location. For families with young Toy Story fans, this is a character experience worth knowing about for summer planning.

Current Diamond Horseshoe Dining: Book Before May 16

The Diamond Horseshoe currently serves an all-you-care-to-enjoy lunch at $45 per adult and $24 per child (ages 3–9), plus tax and gratuity. If the existing buffet-style lunch is on your Magic Kingdom dining wish list, make reservations before May 16. Once it closes for the Jessie’s Roundup transition, the restaurant won’t reopen until fall. The Diamond Horseshoe has been operating in Liberty Square since Magic Kingdom opened in 1971 — it’s a piece of park history worth experiencing.

Planning for Cool Kids’ Summer

If you’re visiting Magic Kingdom during Cool Kids’ Summer (May 26–September 8) and you have young Toy Story fans, Jessie’s Roundup is a natural addition to the itinerary. Character experiences that include interactive activities — crafts, dancing — tend to be more engaging for kids than a standard meet-and-greet. Watch for ticket and reservation details as they become available.

The Diamond Horseshoe’s temporary transformation into Jessie’s Roundup is a smart use of a large, western-themed space during summer season. If you want the current dining experience, book now — May 16 comes faster than you think. And if you’re visiting with Toy Story-loving kids this summer, Jessie’s Roundup looks like a genuine highlight of Cool Kids’ Summer 2026.

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Meet the Author: Nate Bishop

I’m a die-hard Disney fan with 38 years of visits under my belt, having stepped into Disney World 120+ times. Proud to be a Disney Annual Passholder, a Vacation Club member since ’92, a Castaway Club Member, and a runDisney enthusiast. Oh, and I’ve graduated from the Disney College of Knowledge. Need Disney insights or planning tips? I’m your guy!