Destination Main Streets

Kissimmee, Florida

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Kissimmee, Florida has a vibrant downtown that also successfully incorporates its storied past. Kissimmee got its start as a center of transportation. Trains ran north to south in Florida, straight through Kissimmee. From there goods could be shipped by steamboat down the Kissimmee River by way of Lake Tohopekaliga or Lake Toho as the locals call it. Today, trains still travel through Kissimmee whether it's the Sunrail commuter train that takes passengers to downtown Orlando and other points in Central Florida or Amtrak which can whisk travellers across the country. Also, just a few blocks from downtown Kissimmee is Lakefront Park right on the banks of Lake Toho and includes walking trails, pavillions, and even a lighthouse. Today, the shipping industry has long dried up, but many of the cattle ranches that make Kissimmee famous still exist. Signs of Kissimmee's ranching past abound throughout the area, including murals and signs featuring cowboys. The main industry in the area today is tourism as nearby Walt Disney World is just next door.

Downtown Kissimmee features historic buildings along with antique shops and a wide variety of restaurants. Broadway forms the Main Street in Kissimmee. In fact, a road through Kissimmee called Main Street turns into Broadway just as you enter the historic district. Most of the activity can be found on Broadway between Neptune Road and Stewart Avenue. Kissimmee is located in Osceola County, Florida. The city is about 18 miles south of downtown Orlando and 73 miles northeast of Tampa Florida. The Kissimmee Welcome Center is at 421 Broadway so if you set your GPS for that, you should find the area easily. Another nearby Main Street worth checking out is Celebration, Florida.

Photo Gallery Tour

We'll start our tour of Historic Downtown Kissimmee at the corner of Broadway and Neptune Road and from there work our way south. This is the Kissimmee Welcome Station. It was once a filling station but has been restored with artwork and a replica gas pump.
We'll start our tour of Historic Downtown Kissimmee at the corner of Broadway and Neptune Road and from there work our way south. This is the Kissimmee Welcome Station. It was once a filling station but has been restored with artwork and a replica gas pump.
As we make our way south to the intersection of Broadway and Sproule Avenue, we see shops and restaurants. Kissimmee was once known as Cow Town due the importance of the cattle industry in the area. In fact, at one time, Kissimmee was the only city in the U.S. to have grass streets. They were maintained by cattle that would eat the grass.
As we make our way south to the intersection of Broadway and Sproule Avenue, we see shops and restaurants. Kissimmee was once known as Cow Town due the importance of the cattle industry in the area. In fact, at one time, Kissimmee was the only city in the U.S. to have grass streets. They were maintained by cattle that would eat the grass.
Here is a BBQ place with some artwork out front, celebrating Kissimmee's cattle industry, and of course the cuisine inside. A large amount of cattle land was sold off to form nearby Disney World. Cattle ranches still exist in the area to the south of Kissimmee. Today, one of Kissimmee's leading industries is tourism due to the nearby theme parks.
Here is a BBQ place with some artwork out front, celebrating Kissimmee's cattle industry, and of course the cuisine inside. A large amount of cattle land was sold off to form nearby Disney World. Cattle ranches still exist in the area to the south of Kissimmee. Today, one of Kissimmee's leading industries is tourism due to the nearby theme parks.
If we head down a little ways and make a detour on Dakin Avenue, we come across the Kissimmee City Hall.
If we head down a little ways and make a detour on Dakin Avenue, we come across the Kissimmee City Hall.
Back on Broadway at the intersection of Broadway and Dakin Avenue, we have Makinson Hardware Store. Started in 1881, it is Florida's oldest hardware store and Kissimmee's oldest business. Although founded in 1881, it relocated to Broadway in 1900.
Back on Broadway at the intersection of Broadway and Dakin Avenue, we have Makinson Hardware Store. Started in 1881, it is Florida's oldest hardware store and Kissimmee's oldest business. Although founded in 1881, it relocated to Broadway in 1900.
Across the street we see some more businesses along with directional markers that help visitors reach various points of interest throughout downtown Kissimmee.
Across the street we see some more businesses along with directional markers that help visitors reach various points of interest throughout downtown Kissimmee.
Also on the corner of Dakin Avenue and Broadway is Kissimmee City Centre, a mixed-use development, featuring offices, retail, residential, and restaurant space. This site was once home to the Tropical Hotel, built in 1881. It hosted President Chester A. Arthur, the Vanderbilt family, and Thomas Edison before burning down in 1896.
Also on the corner of Dakin Avenue and Broadway is Kissimmee City Centre, a mixed-use development, featuring offices, retail, residential, and restaurant space. This site was once home to the Tropical Hotel, built in 1881. It hosted President Chester A. Arthur, the Vanderbilt family, and Thomas Edison before burning down in 1896.
If we head south on Dakin Avenue, we can see some of the businesses and cafes inside the Kissimmee City Centre that front Dakin Avenue. After the Tropical Hotel on this site burned down, it was replaced by the Graystone Hotel & Casino and Brandow Opera House.
If we head south on Dakin Avenue, we can see some of the businesses and cafes inside the Kissimmee City Centre that front Dakin Avenue. After the Tropical Hotel on this site burned down, it was replaced by the Graystone Hotel & Casino and Brandow Opera House.
Next we find some more historic buildings housing various businesses along Dakin Avenue.
Next we find some more historic buildings housing various businesses along Dakin Avenue.
Just two short blocks south of Broadway, we reach the Kissimmee SunRail Station. The SunRail commuter line takes folks from Poinciana to downtown Orlando and all the way to DeBary, Florida. Amtrak also serves this station.
Just two short blocks south of Broadway, we reach the Kissimmee SunRail Station. The SunRail commuter line takes folks from Poinciana to downtown Orlando and all the way to DeBary, Florida. Amtrak also serves this station.
Next door to the station is the historic Train Depot. This station dates all the way back to 1883. Kissimmee was once a vital transportation hub due to its access to rail and to the waterfront from which steamboats would ship merchandise up and down the Kissimmee River.
Next door to the station is the historic Train Depot. This station dates all the way back to 1883. Kissimmee was once a vital transportation hub due to its access to rail and to the waterfront from which steamboats would ship merchandise up and down the Kissimmee River.
We head back to Broadway. Here on another corner of Dakin Avenue and Broadway is Mach Brothers' Livery Stable built in 1911. The large archway on the left is original and was used for the horses and carriages and eventually Ford Model Ts.
We head back to Broadway. Here on another corner of Dakin Avenue and Broadway is Mach Brothers' Livery Stable built in 1911. The large archway on the left is original and was used for the horses and carriages and eventually Ford Model Ts.
Here we find a row of shops, restaurants, and other businesses along Broadway in Kissimmee, Florida.
Here we find a row of shops, restaurants, and other businesses along Broadway in Kissimmee, Florida.
As we continue down Broadway, we pass more boutiques, salons, and other businesses. Like a lot of towns in Florida, it's not uncommon to have covered walkways to help keep off the sun and rain.
As we continue down Broadway, we pass more boutiques, salons, and other businesses. Like a lot of towns in Florida, it's not uncommon to have covered walkways to help keep off the sun and rain.
Here is another view of the building we were looking at previously. We can see the covered walkway. Also notice the stone street sign on the corner. We're on the corner of Broadway and Monument Avenue.
Here is another view of the building we were looking at previously. We can see the covered walkway. Also notice the stone street sign on the corner. We're on the corner of Broadway and Monument Avenue.
Across the street, also on the corner of Monument Avenue and Broadway is an office plaza with a mid-rise residential tower in the background.
Across the street, also on the corner of Monument Avenue and Broadway is an office plaza with a mid-rise residential tower in the background.
If we walk inside the small office plaza, we find a courtyard with what seems like a unique place for a historical marker. The theme is "The Great Endurance Run," an event where automobiles drove cross-state from Jacksonville to Tampa in a four-day grueling race in 1909. They stopped at the Graystone Hotel on this site.
If we walk inside the small office plaza, we find a courtyard with what seems like a unique place for a historical marker. The theme is "The Great Endurance Run," an event where automobiles drove cross-state from Jacksonville to Tampa in a four-day grueling race in 1909. They stopped at the Graystone Hotel on this site.
We'll head down Monument Avenue now towards the waterfront. Along the way, we see some more retail space on the ground floor of this residential block.
We'll head down Monument Avenue now towards the waterfront. Along the way, we see some more retail space on the ground floor of this residential block.
First, we pass by this park with a small lake in the middle, where we meet Sunrise and Sunset. One horse represents Kissimmee's past while the other represents the city's future. They are part of an overall sculpture experience that features other horse sculptures throughout the city.
First, we pass by this park with a small lake in the middle, where we meet Sunrise and Sunset. One horse represents Kissimmee's past while the other represents the city's future. They are part of an overall sculpture experience that features other horse sculptures throughout the city.
This is the Monument of States, first conceived after the attack on Pearl Harbor. It includes pieces from all over the world, including the 48 states that were part of the U.S. at the time. Construction was completed in 1943.
This is the Monument of States, first conceived after the attack on Pearl Harbor. It includes pieces from all over the world, including the 48 states that were part of the U.S. at the time. Construction was completed in 1943.
Now we reach Kissimmee Lakefront Park, a beautiful city park on the banks of Lake Tohopekaliga or Lake Toho for short. The park includes pavillions, and trails around the lake.
Now we reach Kissimmee Lakefront Park, a beautiful city park on the banks of Lake Tohopekaliga or Lake Toho for short. The park includes pavillions, and trails around the lake.
Here at Lakefront Park, we see a lighthouse. Much of Kissimmee's early growth was tied to the shipping industry. From Kissimmee, steamboats would travel south on Lake Toho to the Kissimmee River and from there to Lake Okeechobee in South Florida.
Here at Lakefront Park, we see a lighthouse. Much of Kissimmee's early growth was tied to the shipping industry. From Kissimmee, steamboats would travel south on Lake Toho to the Kissimmee River and from there to Lake Okeechobee in South Florida.
We head back to Broadway. Here at the corner of Broadway and Monument Avenue we have this office building with a beautiful mural painted along the side of it.
We head back to Broadway. Here at the corner of Broadway and Monument Avenue we have this office building with a beautiful mural painted along the side of it.
This is another view of the office building from the previous photo. Here we can see the cafes along the ground floor.
This is another view of the office building from the previous photo. Here we can see the cafes along the ground floor.
If we zoom in, we find the Kissimmee Diner, one of the many restaurants throughout downtown Kissimmee.
If we zoom in, we find the Kissimmee Diner, one of the many restaurants throughout downtown Kissimmee.
Across the street we find colorful buildings with colorful directional signs as well. The building in the foreground is the Rivers Building, built in 1915.
Across the street we find colorful buildings with colorful directional signs as well. The building in the foreground is the Rivers Building, built in 1915.
As we continue heading down Broadway, we find a large variety of restaurants. There's something for everyone here along Broadway.
As we continue heading down Broadway, we find a large variety of restaurants. There's something for everyone here along Broadway.
This is a pretty cool historic building and something typical of Florida with the covered sidewalks. It houses salons and a music store.
This is a pretty cool historic building and something typical of Florida with the covered sidewalks. It houses salons and a music store.
This is a close-up shot of the building we saw in the previous picture. Here, we can see the businesses along with benches out front and in the shade.
This is a close-up shot of the building we saw in the previous picture. Here, we can see the businesses along with benches out front and in the shade.
We continue down Broadway and find one of the several antique stores in Kissimmee. A cowboy and cowgirl stand out front and are illustrative of Kissimmee's past.
We continue down Broadway and find one of the several antique stores in Kissimmee. A cowboy and cowgirl stand out front and are illustrative of Kissimmee's past.
Here is a long view of Broadway, showing some of the shops, restaurants, businesses, and historical architecture in the area.
Here is a long view of Broadway, showing some of the shops, restaurants, businesses, and historical architecture in the area.
Just across the street is this huge antique shop, Lanier's Historic Downtown Marketplace, with merchandise pouring out on the sidewalks.
Just across the street is this huge antique shop, Lanier's Historic Downtown Marketplace, with merchandise pouring out on the sidewalks.
Inside, Lanier's Historic Downtown Marketplace is filled with all kinds of antiques and other unique finds.
Inside, Lanier's Historic Downtown Marketplace is filled with all kinds of antiques and other unique finds.
Continuing down Broadway we see some more shops, including a jewelry store and a bridal shop.
Continuing down Broadway we see some more shops, including a jewelry store and a bridal shop.
We come to the intersection of Broadway and Darlington Avenue. Here we see a row of colorfully painted historic buildings filled with shops and other businesses.
We come to the intersection of Broadway and Darlington Avenue. Here we see a row of colorfully painted historic buildings filled with shops and other businesses.
Across the street, we find more businesses, salons, and shops in historic buildings.
Across the street, we find more businesses, salons, and shops in historic buildings.
One block down Darlington Avenue is this conveniently located parking garage serving the downtown area.
One block down Darlington Avenue is this conveniently located parking garage serving the downtown area.
Back on Broadway and past Darlington, we find some more colorfully painted shops. The brick building on the right is Dann's Department Store. The ground floor was built in 1909 and the top floors were built in 1912. The store is home to one of the first elevators in Florida, and if you visit the inside, you can still see the old-fashioned elevator.
Back on Broadway and past Darlington, we find some more colorfully painted shops. The brick building on the right is Dann's Department Store. The ground floor was built in 1909 and the top floors were built in 1912. The store is home to one of the first elevators in Florida, and if you visit the inside, you can still see the old-fashioned elevator.
Across the street, we have more businesses, and we see another one of those directional signs that guide folks throughout the downtown area.
Across the street, we have more businesses, and we see another one of those directional signs that guide folks throughout the downtown area.
Here is another view along Broadway. The signage is interesting. The light posts feature various symbols of Kissimmee's heritage. Here we see a tree, but others include cowboy boots and cowboys on horseback.
Here is another view along Broadway. The signage is interesting. The light posts feature various symbols of Kissimmee's heritage. Here we see a tree, but others include cowboy boots and cowboys on horseback.
A lot of the shops in downtown Kissimmee have some pretty interesting storefronts.
A lot of the shops in downtown Kissimmee have some pretty interesting storefronts.
Here at the corner of Stewart Avenue and Broadway, we come to the far southern end of Kissimmee's historic downtown district. This is a view looking northbound on Broadway as if we were entering the distict, hence the Welcome to Kissimmee sign. Pretty cool mural on the right. Kissimmee is known for its cowboy heritage, but that scene looks like something out of Westworld.
Here at the corner of Stewart Avenue and Broadway, we come to the far southern end of Kissimmee's historic downtown district. This is a view looking northbound on Broadway as if we were entering the distict, hence the Welcome to Kissimmee sign. Pretty cool mural on the right. Kissimmee is known for its cowboy heritage, but that scene looks like something out of Westworld.
As we head further down Broadway, the road turns into Emmett Street and we start to find more government buildings. This is the Kissimmee Police Department.
As we head further down Broadway, the road turns into Emmett Street and we start to find more government buildings. This is the Kissimmee Police Department.
Here we have the Osceola County Courthouse, and yes, Kissimmee is the Osceola County Seat. This is a more modern building compared to the older historic Osceola County Courthouse.
Here we have the Osceola County Courthouse, and yes, Kissimmee is the Osceola County Seat. This is a more modern building compared to the older historic Osceola County Courthouse.
And this is the historic Osceola County Courthouse. Built in 1890, it is Florida's oldest working courthouse.
And this is the historic Osceola County Courthouse. Built in 1890, it is Florida's oldest working courthouse.
This concludes our tour of Kissimmee. This is an example of one of the many historic homes that surround the downtown area.
This concludes our tour of Kissimmee. This is an example of one of the many historic homes that surround the downtown area.

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