Slingshot is a three-wheeled, two-seat vehicle that allows you to feel the rush of the road while sitting barely 5 inches above the ground! Experience something brand-new and exciting in the Old Town Entertainment District by renting a Polaris Slingshot and exploring Central Florida in an incredible open-air ride. Central Florida Slingshots is now located at the front of Old Town with its brand new 2026 fleet with unlimited miles. Explore Central Florida on your own or choo

Old Town Entertainment District in Kissimmee is hosting the 7th Annual Fourth of July Celebration with free fun and fireworks for the whole family. Celebrating the Fourth of July is an all-day affair at the Old Town Entertainment District. Old Town’s 7th Annual All-American Fourth of July Celebration ignites with a high-energy showcase of American horsepower, live entertainment and a patriotic fireworks spectacular presented by Old Town and Fun Spot America. The All-America

Once a month, Old Town turns the entertainment district into a full import takeover. This weekend, Old Town Kissimmee transforms into the heartbeat of the import world for one electrifying night! Old Town Import Nights takes place on the first Sunday of each month, returning on Sunday, June 7, 2026, from 4 - 9 pm, bringing together the most jaw-dropping builds, die-hard enthusiasts, and an atmosphere unlike anything else in the area. This is the night the import community has

Hamburger Mary's has rolled into Old Town on the 192, and all your favorite shows are back, and more. American bar and grill chain Hamburger Mary's know for its diner classics and cocktails, served with a side of quirky entertainment, announced in May 2024 that it was to close its downtown Orlando location in the historic Bumby Building after 16 years. The much loved location at 110 W. Church St. closed its doors for the last time on Sunday June 2, 2024, with regular live ent

Old Town is turning the district into a full import takeover with a live high energy performance from DJ Sequoia setting the tone all night long Old Town Kissimmee transforms into the heartbeat of the import world for one electrifying night! Old Town Import Nights returns on Sunday, May 3, 2026, from 4 - 9 pm, bringing together the most jaw-dropping builds, die-hard enthusiasts, and an atmosphere unlike anything else in the area. This is the night the import community has bee

Hamburger Mary's search for a new home is over, rolling into Old Town on the 192. American bar and grill chain Hamburger Mary's know for its diner classics and cocktails, served with a side of quirky entertainment, announced in May 2024 that it was to close its downtown Orlando location in the historic Bumby Building after 16 years. The much loved location at 110 W. Church St. closed its doors for the last time on Sunday June 2, 2024with regular live entertainment includin

As Old Town celebrates 36 years of the Saturday Night Classic Car Show and Cruise, the event continues to attract locals and visitors from all over the world to enjoy a weekly dose of nostalgia and excitement. Located on Highway192 in Kissimmee, Old Town is a unique and iconic entertainment district featuring over 70 unique shops, restaurants, bars, rides, family-friendly attractions, and of course it's famous car shows!. Old Town is an iconic tourist attraction that is still

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, Th

Something big is brewing at Old Town for 2026, with Waggin' Weekend Festival bringing championship-level fun, and touchdown-worthy memories with your four-legged quarterback. Calling all dog lovers! Get ready for the ultimate Super Bowl celebration at Waggin' Weekend Festival, Super Bowl Edition on February 1, 2026 from 10 am - 2 pm at Old Town Entertainment District! This fun event promises to be an epic event featuring live entertainment that'll have you on your feet, plus

Osceola Chamber hosting Three Kings Day 2026 at Old Town Kissimmee on Sunday January 11 The Osceola Chamber will once again host their annual Three King’s Day at Old Town in Kissimmee, with this year's event taking place on Sunday, January 11, 2026, from 10 am - 2 pm. The Feast of the Three Kings is a cherished tradition and a beautiful part of Latin folklore, celebrating the Epiphany and the spirit of giving. This special day holds deep meaning—especially for children—as it

New Year's Eve Celebration at Old Town will feature Free Car Show, Live Music, and Drone Show. Old Town in Kissimmee, the iconic walking district of shops, food, entertainment and events for 40 years, will ring in the New Year with a brand-new drone show by Aerial Illuminations, to light up the sky at midnight. The free New Year’s Eve celebration begins at 6 pm with live music and entertainment, featuring the band DRAW 4 . Plus, Old Town’s signature car show will happen thro

Looking for plans this New Year's Eve? Join Fun Spot America at their Orlando park for fireworks at Midnight, and a spectacular drone show at the Kissimmee park in conjunction with Old Town. Ring in 20265 with a choice of two spectacular celebrations at Fun Spot America in Orlando, and Kissimmee. On December 31, say goodbye to 2025 and r ing in the new year with a classic countdown moment at Fun Spot America Orlando! On New Year’s Eve, the park comes alive with high-energy fu

The cruisers will dressed up to accept toy donation from the public and other cruisers, plus enjoy photos with Santa, and a holiday golf cart parade on the Saturday. Old Town, an iconic walking district of shops, food, entertainment and events for 40 years, will hold its 35th Annual Cruiser Toy Drive this year on Friday, Dec. 5 from 3 to 8 pm and Saturday, Dec. 6, from 1 to 8 pm for both cruisers and the public to donate unwrapped toys. All of the collected toys will be gi

Celebrate the spookiest of holidays at Old Town in Kissimmee with a night of good old fashioned family fun. Grab your little ghoul or goblin for a night of frightful fun at Old Town on Friday, October 31, 2025. Celebrate the spookiest of holidays with free Trunk or Treat, thrilling Halloween entertainment, and a fang-tastic Costume Contest. Collect sweet treats at candy stations throughout Old Town during free Trunk or Treat from 5 pm to 7 pm, while supplies last. Show off yo

Gather your crew and celebrate freedom at Old Town. Groove into the night with live tunes, then gaze up as the sky lights up with...