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Old Town Entertainment District: Timeless Fun
In Kissimmee's Old Town Entertainment District, every day (and night) is a throwback — complete with car shows, a classic Ferris wheel, and live music.
Experience the charm of Old Town Entertainment District, where classic car shows, family fun, and vintage vibes light up the night.
At a Glance
- Old Town Entertainment District is an open-air complex offering a mix of more than 70 retro-themed attractions, classic car shows, unique shops, diverse dining options, and weekly live entertainment.
Since opening in 1986, Old Town Entertainment District has been the hot spot for old Florida fun in Kissimmee. From classic cars to arcade games to international dining, Old Town serves up family-friendly fun with a side of nostalgia.
Captivating Car Shows
Calling all car lovers! Old Town Entertainment District's car shows are the talk of the town and a must-see for automobile enthusiasts. Each week, Old Town rolls out multiple car shows: a themed Wednesday-night show that changes weekly (think Corvettes one week, Jeeps the next), a Friday-night muscle car showcase, and a Saturday-night classic car show. In other words, there’s a good chance you’ll get to admire eye-catching vehicles no matter when you visit.
Experience the charm of Old Town Entertainment District, where classic car shows, family fun, and vintage vibes light up the night.
Live Music & Events
Entertainment-wise, there’s almost always something happening in Old Town Entertainment District. Enjoy live music from Central Florida artists several times each week. Listen to country to rock to pop, depending on the performer, as you eat, drink, and explore the area.
In addition to live music, Old Town hosts a full lineup of fun events. On the first Sunday of every month, there's Latin Fest, a lively (and delicious) celebration of Latin American music, food, and culture. And on the Fourth of July and New Year’s Eve, Old Town is one of the best places in Orlando to celebrate thanks to its iconic firework show.
It's not hard to find live music in Old Town
Kid-Friendly Rides & Entertainment
The old-school carnival rides are a classic feature of Old Town Entertainment District. Go for a spin on the 86-foot Ferris wheel and soak in views of Kissimmee and Orlando. Experience adrenaline-pumping thrills on the five-story Hurricane rollercoaster. Or take a turn on the picture-perfect carousel.
Old Town Entertainment District is also home to hands-on fun, like Happy Days Family Fun Center, an arcade with more than 50 exciting games. Test your racing skills, play a few rounds of Skee-Ball, and cash in your tickets for fun prizes!
Take your kids on the Ferris wheel at Old Town Entertainment District
Shopping for Souvenirs & Gifts
Souvenirs are a vacation must, and the more memorable, the better. Stop into Wound ‘N Around for movie and TV memorabilia from the 1940s, '50s, and '60s. Hit up Old Town Leather for high-quality leather goods. Pose for a faux-vintage photo at the Old Town Portrait Gallery or purchase hand-carved wood wares at Extreme Woodcrafts Gift Shop. And then there’s the Old Town General Store, with just about every time-honored souvenir you can think of.
In search of something with more modern vibes? Shops like Ocean Wave Surf Shop, Shades in the Sun, and Tiki Jim’s are filled with beach-themed goodies like comfy tees and trendy sunglasses.
Explore great shopping, dining and more in Old Town Entertainment District
Classic Fare
No trip to Old Town Entertainment District would be complete without all-American food favorites. Get a quick bite at Nathan’s Famous Old Town. This legendary brand got its start as a nickel hot dog stand in Coney Island in 1916. Today, locations across the U.S. serve up the same hot dogs and fries that have been delighting people for decades.
Head to Flippers Pizzeria for brick-oven pizza with all the classic topping combinations, plus a few outside-the-box recipes. Try the Pig & Pesto, the Hog & Honey, or the veggie pie.
For sweet treats, visit Sweet Dreams Ice Cream Cafe. This charming ice cream shop lets you take your favorite flavor and transform it into an entirely new ice cream creation. Milkshakes, malts, sundaes, and banana splits are just the beginning!
Grab a classic cone at Old Town Entertainment District
Explore more things to do Old Town Entertainment District.
Frequently Asked Questions
Old Town Entertainment District is an open-air attraction in Kissimmee designed as a classic Florida-style town with vintage charm. It features over 70 shops and restaurants, amusement rides, live entertainment, and weekly events such as car shows and live music, making it a popular destination for both families and visitors.
Visitors can enjoy shopping, dining, amusement rides, live music, and themed entertainment. Popular activities include browsing specialty shops, riding the Ferris wheel, watching classic car cruises, attending live concerts, and exploring seasonal events held throughout the week.
Old Town is known for its weekly car shows featuring themed nights, muscle cars, and classic vehicles. The most popular events include Wednesday themed shows, Friday muscle car cruises, and Saturday classic car cruises that showcase vintage and collectible automobiles.
Yes, Old Town is designed as a family-friendly entertainment district with amusement rides, arcade-style attractions, live music, restaurants, and safe walkable streets. It offers activities suitable for children, teens, and adults
Old Town features a mix of souvenir shops, clothing boutiques, surf shops, memorabilia stores, and specialty retailers. Visitors can find unique gifts, retro items, leather goods, jewelry, and themed merchandise throughout the district.
Yes, Old Town hosts live music several times a week, featuring local Central Florida musicians and bands. Performances include a variety of genres such as rock, country, pop, and Latin music, depending on the scheduled event.
Yes. Entry to Old Town Entertainment District is free, and visitors can walk through the district without an admission fee. However, rides, dining, shopping, and certain attractions have individual costs.