On July 21, 1821, there were two counties formed in Florida – Escambia to the west and St. Johns to the east. More than 60 counties were later formed from these two counties.

In 1824, the area to the south of St. Johns County became Mosquito County, and Enterprise was named the county seat. The name was changed to Orange County in 1845 when Florida became a state.

A year before, in 1844, Brevard County was also carved out of Mosquito County. On May 12, 1887, Osceola was named a county, having been created from both Orange and Brevard Counties. At that time Osceola extended all the way down to Lake Okeechobee, and did so until 1917.

Osceola County became Florida’s 40th county and was named after the famed Seminole leader. This area was a transportation hub in the late 19th century for riverboats and railroad and readily began a cattle, sugar, and lumber-based economy.

A vintage postcard featuring the Osceola County Courthouse
Kissimmee Broadway
Broadway, Downtown Kissimmee
St Cloud
New York Avenue, Downtown St Cloud

Osceola County’s 1,506 square miles include the cities of Kissimmee (incorporated in 1883) and St. Cloud (incorporated in 1911), as well as numerous communities.

  • The city of Kissimmee has always had a strong historical association with the Florida cattle frontier.
  • The City of St. Cloud has roots that trace back to a northern land baron who began a sugar plantation in 1881.

Some of Osceola County’s other communities include Narcoossee and Kenansville.

  • Narcoossee is one of Osceola County’s oldest settlements and was home to numerous British immigrants who brought with them a love for the sport of polo. In fact, a team was created in 1888 and grew to more than 100 members just two years later.
  • Kenansville is located in southeast Osceola County and was named for railroad mogul Henry Flagler’s third wife, Mary Lily Kenan Flagler, once he donated five acres and $6,000 to build a school house in 1911.

Source: Osceola County website, www.osceola.org

Osceola History Facts

  • Makinson Hardware in downtown Kissimmee, founded in 1884, was the oldest hardware store in the state until their closure in 2021.
  • The Silver Spurs Rodeo, now the largest east of the Mississippi River, started in 1943, when the riding club members built their rodeo arena on land donated by Henry O. Partin.
  • According to a Kissimmee Gazette article, dated May 17, 1957, the Grissom Funeral Home began painting their ambulances a San Marquis Blue color around 1928. They did this so their clientele would be able to distinguish between funeral coaches and the ambulances. The color is now known throughout the state as the Grissom color.
  • The Monument of States was built by local tourism booster, Dr. Charles Bressler-Pettis. The monument contains 1,500 stones including meteors, stalagmites, petrified wood, teeth and bones.
  • M Bryant, in the early 1920s, cleared a few acres for a campground near the swamp on Old Tampa Highway west of Shingle Creek. Bryant decided to leave the oak trees and opened Bryant’s Auto Camp. He offered campers a shady site, a store, a filling (gas) station and well water.
  • In 1881, Hamilton Disston paid $1 million for 4 million acres of land in Florida. He drained much of the swamps and dredged a river highway from Lake Tohopekaliga to Fort Myers.
  • The first hotel was the Lake House at Kissimmee’s Bryan and Orlando streets, built in the 1880s when Kissimmee was home to a thriving shipyard that built steamboats.
Makinson Hardware Kissimmee
Makinson Hardware, Kissimmee
Silver Spurs rodeo
Silver Spurs Rodeo, Kissimmee
Monument of States
Monument of States, Kissimmee
Bryants Auto Camp, Kissimmee
Bryant’s Auto Camp, Kissimmee
Disston dredge, St Cloud
Disston dredge, St Cloud
Lake House, Kissimmee
Lake House, Kissimmee
Roseada steamboat edited
Narcoossee-Runnymede Hotel
The Runnymede Hotel (near where Chisholm Park is today), early 1920s-1930s.
GAR Hall St Cloud
GAR Hall, St Cloud
Blog posts: Osceola County