What to do at Old Town Kissimmee

Famous for its unique blend of historic charm and modern attractions, Old Town Kissimmee, Florida, is a must-visit destination for anyone looking to explore some really cool places of Central Florida.

5770 W Irlo Bronson Memorial Hwy, Kissimmee, FL 34746

In over 30 years, not much has changed in Old Town.  At least, I like the fact that this place never changes. For me, it’s like returning to my childhood home.  Soon we will be letting out sighs when we’ll see photos of a place that once existed thirty years ago. At the rate Orlando is growing, out with the old, in with the new. But not at Old Town. This place it’s pretty much the same way I saw it 4 years ago and thrity years ago too. Every time I visit Old Town, I can’t help but remember 1993 when I was 16 and I was working in a restaurant here, and yup, not much has changed.

From the shops and restaurants of Old Town Square to the iconic attractions and performances at Fun Spot, Old Town has something for everyone. In this blog post, we’ll take a look at some of the best places to visit in Old Town and what you can do while you’re there. So get ready to explore some of Florida’s really cool places!

A bit of history: Located in Kissimmee, Florida, Old Town is a unique and charming shopping, dining, and entertainment destination that has been a beloved staple in the Central Florida area since 1986.

This nostalgic stretch of road is home to numerous buildings and attractions that evoke a feeling of days gone by. But did you know that Old Town actually has an incredibly fascinating past? ( well, not really) but, it all began in 1883 when Revolutionary War veteran John Moses purchased land in what was then known as Allendale.  Well according to the archives,  the first building constructed on the property was a two-story house for Moses’ family! Over the years, the surrounding land was developed and soon became home to numerous businesses, such as grocery stores, service stations, churches, and more.

What began as a small community has grown into a bustling downtown area known for its friendly atmosphere and diverse selection of shops.  Unfortunately, after many successful years, the area fell into disrepair and was eventually abandoned in the early 1980s. Thankfully, a group of visionary entrepreneurs purchased the property and brought Old Town back to life. Since then, Old Town has become an iconic landmark with something for everyone!

The buildings: Old Town Kissimmee is a bustling hub of activity, especially when it comes to its buildings!

The architecture in Old Town is quite unique; it’s a mix of classic and modern styles, so you’re sure to find something that suits your aesthetic. From the iconic clock tower to the old-fashioned gas station, each building has its own unique charm. And if you’re feeling brave, why not step inside one of the haunted houses? Nothing like getting a little spooked while exploring the town!

The shops: Old Town Kissimmee, Florida, is known for its fun shopping experience.

The shops are filled with unique finds, from souvenirs to clothing and more. It’s a great place to find something special to take home or add to your collection.
Fun fact: Old Town has the largest flea market in Central Florida! There are more than 70 shops and restaurants in Old Town Kissimmee

Unique Gifts, Extreme Woodcrafts Gift Shop, CSTM TGS Show the world who you are. Wild Billie’s Gifts sells something for everyone. 

The shops range from antique stores, boutiques, and gift shops to specialty shops selling products like art, cigars, and jewelry. There are also many one-of-a-kind collections like the Classic Car Museum, the Train Museum, the Kissimmee Gun Show, and the Disneyana Collection, which features items related to Disney and other characters. There is also the Harry Potter Store, where you can find wands, cloaks, and books inspired by the famous series. Whether you’re looking for something unique or just something to take home as a souvenir, Old Town has something for everyone.

The restaurants:Old Town is home to a great variety of restaurants offering all kinds of cuisine.

From Mexican, Italian, and Asian to American classics and more, there’s something for everyone. Some of the restaurants you can find in Old Town include Tijuana Flats, a popular Tex-Mex joint; Havana Café, offering up authentic Cuban eats; and Pizzeria Delfino, serving up delicious Italian food. .

What to expect and prices:

Most restaurants offer dine-in or takeout options.  Prices vary depending on the restaurant, but you can generally find dishes for $10–$15. At Tijuana Flats, you can get burritos, tacos, and quesadillas at a reasonable price. Havana Cafe offers an array of traditional Cuban dishes such as ropa vieja and mariquitas. And Pizzeria Delfino serves up delicious pizzas with unique toppings like fig and goat cheese or sausage and fennel.

Tiki Jim’s is in business to tickle your funny bone.

The attractions: Old Town Kissimmee, Florida, is renowned for its many attractions and sights.

One of the biggest attractions is the antique car show. Old Town hosts America’s longest running weekly car show and cruise every Saturday

Every Saturday night, Old Town holds a car show featuring classic cars from all over the state and country. The show features live music and vendors selling food, drinks, and car memorabilia.

For those looking to take some amazing photos, Old Town offers an Antique Photo Shop. With a variety of props from different eras, visitors can get their photos taken in old-fashioned clothing and pose for an authentic old-timey photo.

Additionally, Old Town provides great spots for photographers of all levels. There are beautiful cobblestone streets, colorful street signs, old-fashioned storefronts, and interesting architecture that are perfect for capturing that classic Old Town charm.

So, if you are looking for a place to have a great time, Old Town Kissimmee, Florida, is the place for you! This historic district has been around for centuries and offers something for everyone. From quaint shops, delicious restaurants, and unique attractions, Old Town truly has it all. Whether you are looking for an afternoon of shopping or a night of entertainment, Old Town is the perfect destination. So what are you waiting for? Pack your bags and head to Kissimmee for an unforgettable experience. We give Old Town a 5-star rating!