May 31, 2026 · News & Updates, Theme Parks

Rounding Up the Fun: Our Guide to Jessie’s Roundup at Magic Kingdom

A New Summer Tradition in Frontierland

Magic Kingdom has a brand new way to beat the heat this season. As part of the Cool Kids’ Summer campaign, the Diamond Horseshoe has been transformed into Jessie’s Roundup. This interactive experience officially kicked off on May 26 and is scheduled to run through September 8, 2026. If you are looking for a spot where your little ones can burn off energy in the air conditioning, this is it.

Our take? This is a brilliant use of the Diamond Horseshoe space. While the venue often serves as overflow seating for Liberty Tree Tavern, turning it into a dedicated play and performance zone gives families a much-needed sanctuary in the middle of a hot park day. With Toy Story 5 hitting theaters on June 19, the timing for this western-themed celebration couldn’t be better.

Live Music and Character Moments

The heart of the experience is the live entertainment. A musician named Dusty Strings takes the stage to lead the crowd in classic western tunes. You can expect to hear favorites like “A Cowboy Needs a Horse” and the brand new “Horseshoe Stomp.” The latter is an original song written specifically for this event, and it really captures that high-energy, rootin’ tootin’ spirit.

Characters like Woody, Jessie, and Bullseye make regular appearances to lead the dance numbers. Unlike a traditional meet-and-greet where you stand in a long line for a single photo, this is a more fluid, atmosphere-style interaction. The performers move through the audience, encouraging kids to yodel and dance along. It feels more like a neighborhood block party than a formal show.

Interactive Games and Activities

While the music is great, the real surprise is the collection of activity stations spread throughout the hall. Disney has set up several low-tech, high-fun games that are perfect for the younger crowd. Here is what you can find:

The quality of these stations is a step up from previous years. They are sturdy, well-themed, and easy for toddlers to jump into without complicated instructions.

Planning Your Visit

If you want to add Jessie’s Roundup to your itinerary, keep these logistical tips in mind. The experience runs daily from 9:30 a.m. to 6:00 p.m. This makes it a perfect mid-day break when the sun is at its strongest. Just remember that strollers are not allowed inside the Diamond Horseshoe. You will need to park them in the designated Frontierland or Liberty Square stroller parking areas before heading in.

Also, keep an eye out for other Cool Kids’ Summer offerings across the resort. This year is packed with additions, including Bluey at Disney’s Animal Kingdom and the new Mickey Mouse Clubhouse Live! at Disney’s Hollywood Studios. It is a great summer to be a young fan at Walt Disney World.

Disclaimer: This information is gathered from various online sources and news outlets. While we strive for accuracy, Disney plans and policies can change rapidly. We recommend double-checking official Disney sources for the most up-to-date information before making final travel plans.

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