Incorporated in 1883 and originally known as Allendale, Kissimmee was first settled by riverboat captain and former confederate major J.H. Allen. Located on the banks of Lake Tohopekaliga, the city emerged during the late 19th century as a brief hub for steamships and open range cattle ranching. While the steamship era quickly declined with the expansion of Henry B. Plant’s railroad through Central Florida, the city remained economically dependent on cattle ranching until the opening of Walt Disney World in 1971.

Since having a population of 7,119 residents in 1970, growth has engulfed the 20.82 square mile city. Today, with an estimated population of 73,597, Kissimmee is the second largest city in the Orlando-Kissimmee-Sanford Metropolitan Statistical Area. With the July 2018 completion of its 17.2-mile southern expansion, Kissimmee’s revitalized historic downtown has become another walkable destination along Central Florida’s SunRail commuter rail line.


Much of downtown falls within the Kissimmee Historic District. Added to the National Register of Historic Places in 1994, it contains 189 historic buildings.

For many years, Kissimmee was known as Florida’s Cow Capital due to an early 20th century law that made the city the only in the country to have grass streets, allowing cows to graze in them.

Built in 1912, this “flat iron” style building was originally occupied by the former Kissimmee Valley Gazette.

Opening its doors on May 6, 1890, the Osceola County Courthouse is listed on the National Register of Historic Places and is the state’s oldest operating courthouse in continuous use. It is also the site of the State’s last sanctioned hanging.

Dedicated in May 1886, the First Presbyterian Church is Kissimmee’s oldest church.