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.

Signage out front indicates the show is for Cool Kids’ Summer and is presented by Babybel. Hours are 9:30 a.m. to 6:00 p.m. daily.

Jessie’s Roundup

This summer, mosey over to the Diamond Horseshoe in Magic Kingdom park for a Toy Story-inspired hoedown full of family fun. Join Jessie, Woody, Bullseye and their pals for a rip-roarin’ roundup packed with singing, dancing, games and other playful activities!

The last show at the Diamond Horseshoe was over 20 years ago, which was Goofy’s Country Dancin’ Jamboree. It ran from 2003 to 2005 after the Diamond Horseshoe Revue closed on February 1, 2003. The Diamond Horseshoe Revue was an opening day attraction at the Magic Kingdom.

Jessie’s Roundup Decor & Activities

The interior of the Diamond Horseshoe is decked out in Toy Story decor, most of which references the Woody’s Roundup television show introduced in Toy Story 2 as the origin for Woody, Jessie, and Bullseye.

The roundup now belongs to Jessie as Woody gave her the sheriff’s badge in Toy Story 4.

Just off-stage, there is a sign for the various performers guests will find at Jessie’s Roundup, namely The Roundup Ropers and Dusty Strings.

Around the stage, guests will find cutouts of various critters from the fake television show, most of which Disney Parks guests would be familiar with as the virtual prized in the Toy Story Mania ride.

The critters can also be found at the base of the stage.

Guests can get their deputy name at this station, personalizing a sticker with an approved nickname based on their choice of a Toy Story character.

The deputy badge is a large sticker guests can wear.

A new character in Toy Story 5 named Blaze is a horse girl, and she owns a horse named Daffodil that the toys will interact with in the film.

Other decor pieces include activities and games for the younger guests, including this activity where they can rope a horseshoe.

Guests can also spot the difference between two Toy Story images of Forky’s wedding to Karen Beverly, or “Knifey”. The sign above features Snappy from Toy Story 5. She is a small purple camera owned by Blaze.

There’s even a small maze activity with Atlas on the sign. Atlas is a talking toy hippopotamus designed to look like a GPS navigation device. Atlas is voiced by comedian and actor Craig Robinson in Toy Story 5.

Jessie’s Roundup Show

The show portion of Jessie’s Roundup has two distinct portions: one with a live singer on guitar featuring Bullseye, and another with dancing and a jumprope act starring Jessie and Woody.

At the beginning of the show, Jessie says that “we may all be strangers now, but when we’re done we’ll be friends, each and every one!” This is a very cute nod to the old Golden and Diamond Horseshoe Saloon Revue shows at Disneyland and Walt Disney World, which featured the song “Hello Everybody”. In the original song, the lyrics are “if you are a stranger, just say howdy stranger, we will soon be friends that way”.

This section has the characters and performers dancing to songs from the Toy Story film series, while interacting with guests during crowd participation portions. Jessie and Woody also come down into the crowd.

The Roundup Ropers come out a few minutes in to take the stage and perform an impressive jumprope routine. They also come out to the floor so children (and the young at heart) can join in on the jumprope fun.

Woody and Jessie return to teach guests the Horseshoe Stomp. The show ends with the pair inviting guests to sing-along to “You’ve Got a Friend in Me”.

The other 15-minute show features Dusty Strings singing and playing the guitar. He also teaches the guests a dance, eventually joined by Bullseye.

Jessie’s Roundup POV Video

You can enjoy the full show experience from Jessie’s Roundup below:

Jessie’s Roundup will be offered through September 8, 2026 for Cool KIDS’ Summer at the Magic Kingdom, following that the Diamond Horseshoe will return to being a table service dining venue.

Will you be checking out Jessie’s Roundup this summer? Let us know on social media.

For the latest Disney Parks news and info, follow WDW News Today on Twitter, Facebook, and Instagram.