Kissimmee has a rich and colorful history highlighted by cattle raising and steamboats that dates back to the 1800s and can still be found to some degree today.

In 19th Century Kissimmee, the livelihood of the town's early pioneers depended on wild cows that roamed the Kissimmee River Valley. Descendants of the cattle left behind by Spanish explorers in the 1500s, the abundance of these wild herds led to Florida later becoming one of the nation’s largest cattle producing states. Before Walt Disney came to town to build his theme park, Kissimmee’s cattle industry was so large that the city was recognized statewide as “Cow Town.” A law passed by Mayor Col. Aderhold around 1885 allowed cows to graze on the city’s grass streets helping to start the “cow town” reputation, and instead of property taxes, residents paid according to the number of cows they owned.

Steamboats came on the scene after Hamilton Disston’s newly dredged canals made the Kissimmee Chain of Lakes navigable to the Gulf of Mexico around 1883.  The shores of Lake Tohopekaliga, which border the city, became a major shipping port.  Ranchers from across the state brought livestock to Kissimmee for shipment to Cuba and elsewhere. Steamboats continued to navigate the Kissimmee Chain for about 40 years, until major highways were built and steamboats were no longer needed. History buffs can learn more about Kissimmee’s steamboat era by visiting the Osceola County Historical Museum and Pioneer Center.

Kissimmee’s cattle ranching heritage can be experienced today at rodeos and working cattle ranches.   Kissimmee is the proud home of the largest rodeo east of the Mississippi River – the PRCA sanctioned Silver Spurs Rodeo. Florida Eco-Safaris at Forever Florida offer half-day round-ups and "City Slicker's Weekend" experiences on Crescent J Ranch.