Downtown Kissimmee: Where Kissimmee Cowboy Legends Come Alive

Step into the heart of Florida cowboy country by visiting Historic Downtown Kissimmee, a destination steeped in rich ranching history. You'll become a modern-day cowboy as you explore this vibrant community, where the legacy of the American frontier lives on. Every year on the fourth Saturday of July, the National Day of the Cowboy celebrates the cowboy way of life across the United States. But in Kissimmee, the spirit of the cowboy can be felt year-round. So, put on your boots, grab your hat, and get ready for a wild ride through Kissimmee’s cowboy culture!

Kissimmee’s Ranching and Cowboy Heritage

Before the theme parks and roller coasters, Kissimmee was known for its sprawling cattle industry. Spanish explorers would lay the foundation for the region’s cattle ranching fame by being the first to bring horses and cattle to Florida. 

By the 19th century, the cattle industry drove economic growth in the area with Kissimmee becoming the “Cow Capital” of the state. It's no wonder the city came to be called “Kowtown,” a nickname honored every year at the Kowtown Festival hosted at Lakefront Park to celebrate Kissimmee’s birthday.

At the heart of Kowtown's history were the cowboys who drove cattle and performed in rodeos. Among the most famous Kissimmee cowboys was Otis “Pete” Clemons, a fourth-generation Floridian and member of a pioneer cattle family. Clemons enjoyed a stellar rodeo career spanning over twenty years, during which he earned the Best All Around Cowboy title eight times at our local Silver Spurs Rodeo. 

You can still find his legacy present today, having inspired Osceola High School’s mascot, Kowboy Jake (yes, spelled with a K!). Kowboy Jake was originally drawn by Florida Artist Hall of Famer E.L. “Buster” Kenton, who found inspiration in cattlemen and bull riders of Kissimmee to create his western-themed artwork. 

Historic Cowboy Landmarks 

From the moment you drive into Downtown, you’ll notice cowboy influence everywhere you go. The intricate arches on Main Street that welcome you to Historic Downtown Kissimmee feature a cowboy riding a bucking horse. Along Broadway, you’ll find more cowboy symbols on street lamps and sidewalks, embracing the city’s ranching legacy. 

As you continue your stroll through Kissimmee, you’ll also notice that the city has a flair for the arts. Several murals tell the story of the city's rich cowboy heritage. These Instagram-worthy murals are part of Osceola Arts' ARTisNOW project, commemorating local culture and community. They make for beautiful photos that capture the essence of Kissimmee’s unique history and creativity. So, get your hat, strike a pose, and become a modern-day cowboy in front of these beautiful murals. Don’t forget to use #MyKissimmee!

One mural noted for its ode to Osceola is the Iron Horse. Located right before the intersection of Broadway and North Stewart Avenue, this stunning mural captures a common scene from Kissimmee's past but with a modern twist: a mechanical cowboy lassoing a wild metal horse. This dynamic scene and artistic style create a rootin' tootin' backdrop for all your picture needs! 

Just a five-minute walk north on Broadway, nestled between East Dakin Avenue and East Sprouts Avenue, is another must-see art piece called Kowtown, honoring Kissimmee’s nickname. This captivating mural showcases a cowboy and cow against a scenic frontier sunset. Located on the side of ScooterVille of Central Florida, Kowtown vividly highlights the cattle industry’s importance to the local area. The eye-catching colors and impressive steer make a perfect photo memory of your cowboy trip to Historic Downtown Kissimmee.

Cowboy Dining Experiences

Once you’ve visited the murals, eat like a modern-day cowboy with some of Kissimmee’s most loved restaurants! For those who crave authentic barbecue, Big John’s Rockin’ BBQ - By the Lake is owned by an Osceola Kowboy alum! 

Known for its mouth-watering smoked meats and unique BBQ blend, Big John’s offers a true cowboy dining experience. The laid-back setting is perfect for enjoying generous portions of savory brisket, ribs, and pulled pork. And of course, any real Kissimmee Cowboy loves Big John’s Biscuits and Gravy for breakfast!

Step back in time by visiting Makinson Hardware. As you stroll down Broadway in Downtown Kissimmee, a large horse statue standing proudly outside a historic brick building signals your arrival at Makinson Hardware — a true landmark in the community for an impressive 137 years. Originally a local go-to destination for hardware supplies, nails, lawnmowers, and more, Makinson Hardware has seamlessly transformed into a lively watering hole where locals gather for happy hour and delicious food.

Today, the interior is decorated with historic Kissimmee photos and memorabilia, including receipts with names and signatures from the pioneer families, offering a unique dining experience that combines the city’s rich culture with classic American bar food. Enjoy Kissimmee-raised beef with their delicious steak or burger while surrounded by the stories and images that shaped this community.