This summer, Magic Kingdom will introduce a new limited-time experience called Jessie’s Roundup at the Diamond Horseshoe in Frontierland. As part of the Cool Kids’ Summer activation, this event will bring Toy Story characters and interactive fun to guests of all ages. Here’s what you can expect from this new summertime addition.
What is Jessie’s Roundup?
Jessie’s Roundup is a western-themed event featuring beloved characters from Disney and Pixar’s Toy Story franchise, including Jessie and Woody. Guests will have the opportunity to participate in activities such as crafting, dancing, and yodeling in a lively, air-conditioned setting. The Diamond Horseshoe will transform into a vibrant space where families can enjoy energetic entertainment and character interactions.
Event Dates and Details
Begins
May 26, 2026
Ends
September 8, 2026
Jessie’s Roundup will run from May 26 to September 8, 2026, making it a perfect summer activity for guests visiting Magic Kingdom. The event is part of the Cool Kids’ Summer initiative, which aims to provide unique and engaging experiences for younger visitors and their families. Also, in these date ranges Disney World is extending their Free Water Park admission promotion for check-in days between the same May 26 to September 8 date range.
What to Expect at the Diamond Horseshoe
Just for Cool KIDS’ SUMMER, pals from Toy Story are ready for a rootin’ tootin’ good time at the Diamond Horseshoe at Magic Kingdom. Join Jessie, Woody, and friends for some energetic fun at Jessie’s Roundup, where you’ll craft, dance, and yodel your hearts out in this western revue.
Walt Disney WorldDuring Jessie’s Roundup, the Diamond Horseshoe will clear its tables to create an open space for interactive activities. Guests can look forward to:
- Character Meet-and-Greets: Spend time with Jessie, Woody, and other Toy Story friends.
- Interactive Activities: Participate in crafts, dance along to western tunes, and try your hand at yodeling.
- Family-Friendly Fun: The event is designed to be inclusive and enjoyable for guests of all ages.
Conclusion
Jessie’s Roundup at the Diamond Horseshoe promises to be a fun and interactive addition to Magic Kingdom this summer. With its engaging activities and beloved characters, it’s sure to be a hit with families and Toy Story fans alike. Be sure to include this limited-time event in your summer plans at Walt Disney World!
Written by
Rachel Van Norman
Contributing Writer
Rachel fell deeply in love with all things Disney as a little girl. Now as a wife and a mother herself, she shares this Disney obsession with her son and everyone around her. From her love of princesses to eating all the Disney food, Rachel spends her time radiating Disney magic and keeping everyone up to date on Disney news.
