Pioneer Village in Kissimmee: Step Back in Time Just Minutes From Disney

For Orlando locals, we know that the stretch of 192 in Kissimmee is a treasure trove of old-school activities for families, from Medieval Times to Old Town and Fun Spot, but just minutes off that main drag of kitschy, touristy fun, step back into Central Florida’s past at Osceola County’s Pioneer Village.

Browse the authentic homesteads and the living conditions of the old Florida Cracker homes, including a reconstructed town complete with a General Store, Schoolhouse, Church, and more. 

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If you’re looking for activities for kids in Orlando, Pioneer Village is a low-key experience near Walt Disney World, but uniquely historic. Here’s what to expect.

What to Expect

Pioneer Village is one of the most interesting outdoor activities in Orlando.

Showcasing the spirit of the early Florida settlers, the late 1800s village boasts both replica and authentic structures that once stood on Osceola County lands. Relocated to preserve and highlight our Central Florida past, visitors will get to enjoy a stroll in the country, without leaving the Shingle Creek area of Kissimmee. 

Enjoy the stroll as you pop in and out of varying buildings, including the general store, where an old printing press can be seen or even put on demonstration during Pioneer Day (more on that below), a schoolhouse complete with the old furniture, where you will learn that up to 25 children of varying ages and grade levels used to study.

The church, now doubles as an event rental for weddings, is a beautiful example of the town’s place of worship for the pioneers. On my recent visit, I enjoyed seeing the citrus packing plant and the old homes – the kids were fascinated by how a whole family would live and sleep in a one-room house. 

Pioneer Village is just steps from one of our favorite free museums in Orlando, the Welcome Center & History Museum of Osceola County. So while Pioneer Village does have a small admission fee, the indoor museum located at 4155 W. Vine St. Kissimmee is free.

Annual Pioneer Day Event

On Pioneer Day, an annual event heralding the life and times of these pioneers, see the whole village light up with excitement as demonstrations and other activities bring everything to life.

A free, family-friendly event, Pioneer Day kicks off Florida Fall (typically just after Halloween), for a day full of fun for everyone. When I visited with my family this year, everyone found something interesting to do!

We got to witness a blacksmith workshop, the kids got to create their own ropes with antique equipment, and they even got to pump water from an old well.

The highlight, I think, was the yard games, including an actual game of cricket! We all took a stab at manning the ‘outfield’ and hitting some balls around. I don’t think I’ve fully grasped the game yet, but it was a very fun and educational experience!

In addition to the Pioneer Day demonstrations, discover local handicrafts and sweets at the market vendors, including old wooden toys and on-the-nose gifts and souvenirs like beeswax candles or freshly forged iron ware.

Live music set the tone of the day with old country favorites.

We saw many families entering the Pioneer Day event in period outfits – girls in bonnets and the like. It was adorable, but of course not necessary. I did wear my widebrimmed farm hat, though – there’s not a ton of shade!

Location and Info

Pioneer Village is located at 2491 Babb Rd., Kissimmee FL
407-396-8644
Tickets: $8 adult, $4 child

• On a regular day, admission costs $4-8, which does not include a guided tour. If you want a guided tour, you have to arrange that in advance. Kids under age 4 are free.
• Parking is easy on a large grass lot, even on Pioneer Day, but you may want to wear proper sneakers or even cowgirl boots to set the mood and not sink into the grass (or muddy bits if it rains).
• Professional photography is allowed at Pioneer Village for a fee. Please email venues@osceolahistory.org to inquire.

All in all Pioneer Village in Osceola County makes for a great visit if you are interested in the history of Florida settlers. 

If you like these sorts of places, be sure to also check out Fort Christmas, which is always free of charge. They also have the best Florida Cracker Christmas market every holiday season!