Mary Poppins and Bert Stroll Main Street USA in Jolly Holiday Fashion

It’s always a jolly holiday to see Mary Poppins and Bert during a visit to Magic Kingdom or any of the theme parks, for that matter. The pair has been a staple at Walt Disney World for as long as I can remember. When we first started covering characters back in 2019, you could find them regularly greeting guests along Main Street USA. They would usually be available off and on until about 10:00 a.m. After that, Mary would move to the Liberty Square gazebo, which at the time was her regular meet-and-greet spot. If you got there early enough, you might catch Bert meeting with her.

Then in 2020, when character meet-and-greets became sightings, we would find both Mary and Bert in a few of the calvacades. They eventually became pretty regular characters in the Adventure Friends cavalcade, which is still (as of publication) offered daily. The only other regular place to meet Mary Poppins was in the United Kingdom Pavilion at Epcot. That meet-and-greet location ended in 2023. We do still see her from time to time as part of character training at Epcot and Disney’s Hollywood Studios. Those occasions are, however, more random, surprise-and-delight offerings.

So on a recent visit to Magic Kingdom, we were delighted to run into both Mary Poppins and Bert in their jolly holiday costumes. You may remember that these outfits are from a scene in the original Mary Poppins, where the characters jumped into a chalk drawing and went on a jolly holiday. The lyrics, It’s a Jolly Holiday with Mary, come to mind, written by the Sherman brothers.

Of course, this was only a surprise and delight sighting. But it’s a good reminder that it’s okay to take your time and linger on Main Street, U.S.A., a little longer than everyone else. You never know who you might see. Timing is everything. Here are a few more photos.

We’ll have a few more character updates in the near future, including:

• Where to Look for Raya at Magic Kingdom
• Minnie’s New Look at Red Carpet Dreams

Mary Poppins and Bert are part of our historical character index. We have the following character spotlights available: Mary Poppins, Bert

We’ve also recently updated our guide to meeting characters at the 2025 Mickey’s Halloween Party. Some of our favorites this year included:

• Lady Tremaine and the Evil Stepsisters at Mickey’s Halloween Party
• See Maleficent and the Evil Queen at Princess Fairytale Hall
• Meeting Mickey and Minnie Mouse Together at the 2025 Halloween Party
• Where to Find Gaston at Mickey’s Not So Scary Halloween Party

More Planning

Resorts Gal specializes in Disney World Resorts, Characters, and Dining. Explore our resources, including our Disney World Resorts Guide. It provides an overview of everything you need to know about the Disney Resort Hotels. For dining, our Disney World Dining Guide is an excellent place to start. Our Disney World Transportation Guide is a wonderful resource for planning your routes. It’s one of our most popular resources. If you plan to meet characters in the parks, we have an updated list of Disney World Characters. It includes every available character meet-and-greet in the parks, as well as where to find rare characters throughout the year. Lastly, our Disney Parks Guide provides a complete overview of all four theme parks and water parks.

In the Comments

Have you ever seen Mary Poppins and Bert in their Jolly Holiday costumes? Let us know in the comments section below.