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The Kingdom Insider

Orlando and Family Travel News Lifestyle and Information

Disney News, Magic Kingdom, WDW News · June 4, 2026

Honest Review: Jessie’s Roundup at Magic Kingdom

If you’re visiting Walt Disney World Resort this summer, there’s a brand-new experience that families won’t want to miss—Jessie’s Roundup: A Rip-Roarin’ Revue! at Magic Kingdom.

Source: Kingdom Media

This limited-time offering, part of Cool Kids Summer, happening now through September 8, brings extra entertainment, character experiences, and family-friendly fun to the parks and resorts.

What is Cool Kids Summer?

Cool Kids Summer is a seasonal celebration across Walt Disney World focused on creating unforgettable moments for families.

From interactive shows to character experiences and resort activities, it’s all about giving kids (and parents!) even more reasons to enjoy a summer Disney vacation.

What is Jessie’s Roundup?

Located inside The Diamond Horseshoe, Jessie’s Roundup has taken over the space for the summer—temporarily replacing its usual dining service to make room for this interactive experience.

Source: Kingdom Media

The show features:

  • Music and live entertainment
  • Toy Story characters like Jessie, Woody, and Bullseye
  • Interactive games and dancing
  • Audience participation moments
Source: Kingdom Media

What to Expect

Going into it, expectations might be unclear—but this experience truly surprises in the best way.

There are two rotating sets:

  • One featuring Jessie and Woody
  • One featuring Bullseye
Source: Kingdom Media

Throughout the show, guests will also enjoy live performers, including a singing cowboy, dancers, and a group of jump ropers known as The Roundup Ropers—a unique and fun addition that adds a western twist.

Interactive Fun for Kids

Between sets, the room is filled with Toy Story and western-themed games for kids to explore and play at their own pace.

During the show, the characters come right into the audience, making it feel personal and engaging.

Some standout moments include:

  • Jessie and Woody teach a group dance
  • A hilarious yodel competition
  • “Bullseye Says” (a Toy Story spin on Simon Says), hosted by Bullseye and the singing cowboy

These interactive elements were a huge hit with younger guests.

The Perfect Break from the Heat

One of the biggest perks of Jessie’s Roundup is that it takes place indoors, under air conditioning, making it a great midday break from the Florida heat. It’s the perfect combination of entertainment and relaxation, especially for families needing a reset during a busy park day.

Jessie’s Roundup: A Rip-Roarin’ Revue! is easily one of the standout offerings of Cool Kids Summer. With its mix of live entertainment, character interactions, and hands-on fun, it delivers an experience that feels both high-energy and memorable.

For families visiting this summer, it’s a must-do, and one of the best ways to enjoy Disney magic while staying cool. Catch it now through September 8 at Magic Kingdom before Cool Kids Summer comes to an end!

Are you ready to book your Disney vacation? Leave all the details to our friends at Academy Travel Agency & let one of their Disney experts take it from here! Just click here to select your Disney destination of choice, fill out the quick & easy questionnaire, and your personalized, free agent will be in touch soon! Take a look around our website in the meantime, and read all about resorts, cruises, dining, entertainment & more! Be sure to follow us @thekingdominsider on Instagram & The Kingdom Insider on Facebook for updates & Insider info on what’s not to be missed! Get excited; the countdown to your vacation is ON!

Posted By: Brooke Bohannan · In: Disney News, Magic Kingdom, WDW News

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