Businesses on Broadway Avenue in Historic Downtown Kissimmee.

Kissimmee

Long before European settlers came to Central Florida, the land was inhabited by a Native American tribe called the Jororo. It is from this tribe’s language that the name Kissimmee, or “long water” can be traced. 

At the time, Central Florida was swampland and the headwaters of the Everglades extended as far north as Lake Tohopekaliga (Lake Toho for short), the largest lake in Osceola County and one of the country’s most famous lakes for bass fishing.

But it wasn’t until the end of the Civil War that this area began to be developed. Among the war veterans and industrialists who headed to Central Florida in hopes of making their fortunes was Hamilton Disston, who purchased four million acres of land from the State of Florida in 1881 for 25 cents an acre. Disston dredged a canal, drained the swamplands and opened the area’s waterways, creating a port city named Allendale, later renamed Kissimmee City and incorporated in 1884.

The following years would see the creation of Osceola County, and Kissimmee as its county seat. Its main thoroughfare was Broadway Avenue, which today is still an important street in Kissimmee’s Historic Downtown. Learn more about Kissimmee’s early days and pick up a map at the Kissimmee Main Street Welcome Center at Broadway Avenue and Neptune Road, right as you approach downtown. The map details each historic site, telling what it was once used for and what it is today.

The Monument of States was constructed after the attack on Pearl Harbor in 1941 and is a a symbol of American unity.

Living History

In addition to being a port city, Kissimmee also became a rail city, starting in its earliest days. Henry Plant built his railroad depot in 1883 to connect Downtown Kissimmee to Sanford and Tampa, which are now served by Amtrak (and additional locations via SunRail).

One of Florida’s most iconic monuments is found in Downtown Kissimmee. Constructed in 1943 after the attack on Pearl Harbor, the Monument of States is meant to inspire American solidarity by incorporating a rock from each state. A true testament to community, Kissimmee’s generous donors made the monument a reality. If you bring back one selfie from your time in Kissimmee, this should be it. 

OK, maybe you want a second selfie. How about the Osceola County Courthouse, with its red bricks and its steps reminiscent of a scene in “Rocky” (be sure to have water with you should you decide to run up it, though). It’s the county’s original courthouse, opening in 1890, and today is the oldest working courthouse in the state of Florida. 

Kissimmee has a large Hispanic population, reflected in events such as the Viva Osceola festival at Lakefront Park.

The Latin American Connection

Kissimmee’s population is 70 percent Hispanic, reflected in Downtown’s fabric. Cuban, Puerto Rican and Spanish restaurants are plentiful and range from corner nooks to larger concepts. Try Buchito for Cuban coffee done right, plus sandwiches, smoothies and decadent desserts. Sabor del Caribe gets high marks for Spanish cuisine and is a popular spot for karaoke. Matador Tacos and Tapas Bar is an unassuming breakfast and lunch spot, but gets spicy as the night progresses. And one of Downtown Kissimmee’s newer restaurants, Pa’l Callejon, delights diners with its Puerto Rican dishes and live music. 

Never miss a beat when you head for the dance floor—visit Salsa Heat. It’s the largest Latin dance studio in Central Florida. Whether you’re a beginner or on the competitive dance circuit level, no one will be able to tell after the professionally trained instructors are through with you! 

Runners at sunset on Valencia College’s Osceola campus in Kissimmee.

Antiques Please 

Downtown Kissimmee has not one but two antique malls, across the street from each other on Broadway Avenue. Lanier’s Historic Downtown Marketplace is a 10,000-square-foot antique mall full of Disneyana and other collectibles, a great selection of furniture, dishes, items for the garden and so much more—be sure to explore every nook and cranny. Great deals can be had here and there’s almost always sale merchandise. Echoes of Yesterday is another must-stop, with a stunning selection of rare and vintage clocks, cameras, artwork, vases and other décor, plus collectibles as far as the eye can see.

A fisherman starts his journey at Kissimmee Marina.

From Wetlands to Resort Corridor

Kissimmee is known at the gateway to Orlando’s resort corridor, but did you know it’s located in the center of the Great Florida Birding Trail, which runs 800 miles across the state? The Kissimmee Lakefront Park affords great birding opportunities for Snail Kites, Limpkins, Wood Storks, Fulvous Whistling-Ducks, Boat-tailed Grackles, Snowy Egrets, Purple Martins and Ospreys. Sightings of our country’s national bird are also plentiful; the area is home to the largest nesting population of Bald Eagles in the 48 contiguous states. 

Main Street Orlando