A Local’s Guide to Historic Downtown Kissimmee

See Downtown Kissimmee's top historical buildings and sites during your visit.

Girl in yellow dress takes photo in front of Monument of States in Downtown Kissimmee.

Capture the moment at the Monument of States in Downtown Kissimmee

Downtown Kissimmee is nearing 150 years of existence and has changed from a small agriculture town to a bustling cultural hub. Despite these changes, you can still see the historical charm of the town by simply walking down the street. For the history buffs, we’ve gathered a list of all the historical buildings and sites courtesy of some locals that you’ll want to explore in Downtown Kissimmee during your trip.

Kissimmee Main Street Welcome Center

Once a filling station, the Kissimmee Main Street Welcome Center should be the first stop on your tour of Downtown Kissimmee. Located at the corner of Broadway and Neptune Road, this information center has artifacts from Kissimmee’s early years and provides guests an in-depth description of other historic buildings and stories on the downtown area. They even have a map you can pick up to visit each historic site and learn about what it used to be and what it is today.

Broadway Pizza Bar

As you walk down Broadway, you’ll pass by Broadway Pizza Bar, a local favorite serving up cheesy pizza and tasty calzones. This building was actually an old Coca-Cola Bottling Company, and then a local bicycle shop until the owner purchased it in 2008. While the interior has completely changed, you can clearly make out where the old signage used to be and see some historic photos of Kissimmee while you wait for your crispy crust to arrive. They’re very allergy friendly with gluten-free and vegan options, too!

Kissimmee Train Station

The Kissimmee station was originally built as a South Florida railroad depot in 1883 by Henry Plant and was eventually acquired by the Atlantic Coast Line Railroad in 1910. Initially, this railroad transported residents and visitors from Downtown Kissimmee to other Central Florida cities like Tampa and Sanford. You can still take the Amtrak to those destinations today in addition to the commuter rail locations added in 2018 via SunRail. You and your family can use it to visit various local cities across Osceola, Orange, Seminole, and Volusia Counties via the SunRail Kissimmee Station. Fun Fact: The far patio of the train station shows an old wagon cart from the early railroad days.

Fun Fact: The far patio of the train station shows an old wagon cart from the early railroad days.

The Monument of States

Just down the street on East Monument Avenue and Lakeview Drive, you’ll find one of Downtown Kissimmee’s oldest and most significant local landmarks. This marker was initially constructed after the attack on Pearl Harbor to inspire American solidarity by incorporating a rock sent from each state. When the monument was built in 1943, it took many donors from all over the community to make it happen, and their names are in the concrete surrounding this city icon. Its architects were big on generating tourism for the town, so when you visit, be sure to find your state in the monument, and let the world know where you’re visiting from using #MyKissimmee on social media.

Old Kissimmee Gazette Building

As you make your way back to Broadway, continue on to N. Stewart Avenue to see one of Downtown Kissimmee’s most eye-capturing architectural treasures. Built in 1912 as the Kissimmee Valley Gazette, the design of this two-story, brick beauty was inspired by the famous Flatiron building in New York City. While the newspaper, now known as the Osceola News-Gazette, has moved just down the street, this triangle-shaped landmark is still recognized by the American Institute of Architects for its link to pioneer Florida newspapers. It currently serves as a coworking space for small businesses and remote workers.

The Osceola County Courthouse

Continuing down Broadway Avenue toward John Young Parkway, you’ll start to notice some iconic red bricks and Rocky-like steps to an old courthouse. The county’s original courthouse opened on May 6, 1890 and is actually the state of Florida’s oldest working courthouse. While it’s still actively hearing cases, this site can serve as a beautiful backdrop to any family photos you want to take! The old courtroom is on the third floor, and if you drive by at night, you can see the light in the old jail cell room that cannot be turned off to this day! Can you find the switch?

This local guide represents just a few things you can explore while visiting Downtown Kissimmee. To discover more, follow us on our social channels to squeeze in a few extra things while you’re here. And if you want to know even more about all the things you can do in Kissimmee, be sure to sign up for our newsletter.