August 29, 2021

Kissimmee, Florida Things To Do, Lodging, Dining, & Real Estate At End Of Article

Kissimmee, Florida is 22 miles south of Orlando and 12 miles southeast of Walt Disney World. The correct way to pronounce its name is kiss-IM-mee

Its 2020 population is 77,000, and it is the County Seat of Osceola County.

Colorful Historic Downtown KissimmeeColorful Historic Downtown Kissimmee

A couple of lakes in the area are Lake Tohopekaliga and East Lake Tohopekaliga.  Locals simplify things by calling them "Toho", as in Lake Toho.

Until recent years the main route to reach Kissimmee from Orlando was on US-441, known in Orlando as Orange Blossom Trail and in Kissimmee as Main Street.

Wizard Gift Shop On US-192 in KissimmeeWizard Gift Shop On US-192 in Kissimmee

Much of the traffic originally focused on the combined US-441 and US-17 through old downtown Kissimmee has been bypassed by the construction of John Young Parkway that passes west of downtown and carries traffic south into US-17.

There are now many roads leading to Kissimmee and you can consult the Google map at the bottom of this page for more information.

The city limits extend along US-192 westerly to State Road 535 and beyond to several main routes to the Disney resort area. 


The original name of the city was Allendale, named after Confederate Major J. H. Allen.  He operated the first cargo steamboat along the Kissimmee, named Mary Belle

This boat is mentioned in the classic Florida historical novel, "A Land Remembered" by author Patrick Smith.

Broadway Avenue, Kissimmee, About 1912Broadway Avenue, Kissimmee, About 1912

The name changed when the city was incorporated in 1883.

Kissimmee had a strategic location during the early days of Central and South Florida economic development. 

It is located on the north shore of Lake Tohopekaliga, one of a a group of lakes that form the headwaters of the Kissimmee River.

The actual headwater is in nearby East Lake Tohopekaliga. The river flows south through Lake Cypress, Lake Hatchineha, and Lake Kissimmee.  From there it flows down to Lake Okeechobee.

The river was originally 134 miles long, and 103 miles were between Lake Kissimmee and Lake Okeechobee.

Kissimmee began to boom shortly after Hamilton Disston of Philadelphia based his 4,000,000 acre drainage project in the city.

Disston had contracted with the financially strapped State of Florida to drain the acreage.  In return, he would receive half of all lands he successfully drained.

Disston's large dredging and land speculation efforts created a demand for a shipping industry to transport people and goods down the Kissimmee River system to Lake Okeechobee.

Kissimmee even had a shipyard and built some of the steamers that plied the river.

This boom period didn't last long.  The railroads began to come into the area and steamship operations couldn't compete. 

To top it all off the Panic of 1893 created a huge depression and the giant freezes of 1894 and 1895 wiped out the citrus industry.

Bulls on DisplayBulls on Display

By the turn of the century, Kissimmee and Osceola County began to focus more on open range cattle operations.

Raising cattle is still an important factor in the life of Kissimmee, St. Cloud, and southern Osceola County.  This fact can be observed in the annual Silver Spurs Rodeo held in Kissimmee.

It was at one time one of the largest rodeos in the United States and still bills itself as the largest rodeo east of the Mississippi River.



Like many other Florida locations, Kissimmee is a "tale of two cities." The way it is, and the way it was.   

I call these two entirely different cities Touristy Kissimmee and Historic Kissimmee.


When you head south from US-192 through the welcome gate into historic Kissimmee, things begin to quiet down.  There are many historic buildings and attractive old trees.

Looking South from US-192 Into Historic Downtown KissimmeeLooking South from US-192 Into Historic Downtown Kissimmee

Main Street merges into Broadway, and both thoroughfares have landscaped boulevard medians. 

The busy John Young Parkway bypasses the historic downtown area which means it is a quiet place to visit.

One of the oldest businesses on Broadway is Makinson Hardware.  It was established in 1884 and is reported to be the oldest retail hardware store in Florida still in operation.

One of my favorite places to visit in historic Kissimmee is the Monument of States.  It is unlike anything I've seen before. 

I have been awed by it since first seeing it in the 1960s.

Monument of States, Kissimmee, FloridaMonument of States, Kissimmee, Florida

It was inspired by the Japanese attack on Pearl Harbor on December 7, 1941. 

A retired doctor (Charles W. Bressler-Pettis) was president of the Kissimmee All States Tourist Club.  This club's membership was mostly retired senior citizens.

He and a friend got together and designed a monument whose construction was to include at least one rock from each of the states in the United States of America.  

The mission of the monument was to demonstrate the unity of America. 

It was built mostly by volunteers, including many older people from the tourist club and was dedicated in 1943 by U.S. Senator Claude Pepper of Florida.

Historic Osceola County Courthouse, photo by EbyabeHistoric Osceola County Courthouse, photo by Ebyabe

Another favorite downtown spot is the historic Osceola County courthouse.

Kissimmee has done a good job of creating open space and parks along the shoreline of Lake Tohopekaliga. 

There are plenty of walkways, green spaces, and good opportunities for just relaxing.

Kissimmee Lakefront Park on Lake TohoKissimmee Lakefront Park on Lake Toho

Kissimmee Lakefront Park is the showcase of historic downtown Kissimmee.  This park has a fishing pier, walking paths, picnic pavilions, a playground, and lots of shade trees.

An annual event that has taken place since 1950 is usually begun in Lake Toho. 

Named the Kissimmee Boat A Cade, it is a small boat event where a large group of boats takes a trip somewhere in Florida or even beyond.

Kissimmee Boat A CadeKissimmee Boat A Cade

Hundreds of boats travel together and go to a wide variety of places.  They stop at marinas and campgrounds along the way and enjoy fellowship and good food and drink.



Kissimmee was affected more by the opening of Walt Disney World in 1971 than any other Central Florida city.

The population has exploded from 7,100 to 77,000 in the years since the theme park opened.

Touristy Kissimmee is generally the stretch east and west of town along US-192 that extends through Kissimmee from St. Cloud and west to the Disney resorts. 

This is the route that is heavily traveled by tourists who enjoy more reasonable dining and lodging prices than what they can get at the Disney resorts.

What was once empty pastureland and woods for miles along US-192, US-441, and State Road 535 is now a never ending parade of neon lighted tourist gift shops, motels, restaurants, smaller tourist attractions, and other businesses.

These ventures are designed to serve the needs of tourists visiting central Florida's theme parks.

Old Town in KissimmeeOld Town in Kissimmee

One of the more interesting venues is Old Town. 

This is an open-air walking district and entertainment center with more than 70 different shops, restaurants, bars, and amusement park rides.

The complex is a good imitation of a  classic Old Florida town with a lot of period architecture and unique storefronts. 

One of the more popular rides here is the 86 foot tall Ferris Wheel.

Homes in a Celebration NeighborhoodHomes in a Celebration Neighborhood

Another nearby point of interest is the town of Celebration.  This is an actual master planned community created by Disney. 

Citizens of Celebration live and work in a pleasing architectural environment that captures the spirit of classic old Florida and American neighborhoods.

Downtown CelebrationDowntown Celebration

Although the master planned community of Celebration is not in Kissimmee, it is close enough to deserve a visit.

Learn more about Celebration, Florida.


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Mike Miller of has written 25 books on Florida.  

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