Old Town Entertainment District in Kissimmee celebrates 40 Years of Quirky Cool!

Join the celebrations as Old Town, the home to the longest running car show and car cruise in America celebrates its 40th Anniversary.

Old Town in Kissimmee is celebrating 40 incredible years of its Quirky Cool brand of fun and entertainment and invites you along for the ride.

With 47 shops, 23 restaurants and bars, seven rides and attractions, there’s no mistake that Old Town has something for everyone.  Add to that, free weekly events, including Wednesday’s Bike Night, Thursday Night Karaoke, Friday Night Muscle Car Show & Cruise, Saturday Night Classic Car Show & Cruise and free live music every Sunday, Wednesday, Friday, and Saturday. 

Visitors can’t miss Old Town’s giant 42-feet-high Neon Jukebox Signs, Italian-made Signature Ferris Wheel with 6,260 lights and 18 gondolas that took 15 days to install, and charming Clock Tower imported from Europe.  The Saturday Classic Car Show and Car Cruise, taking place at Old Town for the last 36 years, is the longest running car cruise in America.  And the Old Town stage hosts hundreds of local bands each year.

For seven of the 40 years, from 1986 to 1992, Little Darlin’s Rock & Roll Palace was the “in” place to go at Old Town, featuring super stars from the 50s and 60s like The Platters, The Coasters, The Van-Dells, Gary U.S. Bonds, Frankie Avalon, Fabian, Peter Noone, Joe Walsh, Jim Stafford and Micky Dolenz.  In 1989, the name was changed to Wolfman Jack’s Rock N’ Roll Palace. The popular three-floor venue was featured in syndicated televised shows of Rock N’ Roll Palace, hosted by Wolfman Jack.

Through the years, Old Town has been dedicated to giving back to the community through signature events such as its annual Cruiser Toy Drive benefiting Osceola County and hosting the Osceola Chamber’s annual Three King’s Day event.

“Old Town means so many different things to so many people,” says Thearon Scurlock, Vice President and General Manager of Old Town.  “Lots of locals and visitors remember seeing their favorite performer at Little Darlin’s.  Others come every single week to our Classic Car Show and Car Cruise, our Bike Night or to listen to free live music while visiting all our shops and restaurants. We are continually adding new experiences and new events like our brand-new Drone Show for New Year’s Eve and Fourth of July.  So be on the lookout for what we have coming next!”

About Old Town

Built in 1986, Old Town is the recreation of a classic Florida town at the turn of the century featuring historical architecture and distinctive storefronts.  Located on U.S. 192 in Kissimmee,

Old Town boasts over 70 unique shops, themed restaurants and bars, rides, weekly car shows, and family-friendly attractions. 

Celebrating its 40th anniversary in 2026, Old Town has been a favorite destination for locals and tourists alike looking for the simple pleasures of classic American fun. 

For the full schedule of weekly and monthly events at Old Town, go to www.myoldtownusa.com.

Never miss anything happening in Orlando again, we've got you covered with the latest and best things to see and do throughout Central Florida. Get the Latest Orlando News now!

Contact Us:

You can contact us here. To advertise with us, click here. To list your upcoming event, submit it here.

Newsletter:

Sign up for our newsletter and stay in the loop with all the latest news from Central Florida delivered daily to your mailbox.

Social Media:

Join the local conversation on X, Facebook, and Instagram, plus, for extended coverage, catch the latest on our YouTube channel.