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Old Town in Kissimmee, FL: Good Old Fashioned Fun is Never Outdated!

Once upon a time, “crowds were a little smaller, lines a little shorter, and the fun a little simpler.”1 While much of the world has moved on since those halcyon days, opting for all things new and flashy, Old Town amusement park in Kissimmee, Florida, continues to espouse the old ways. Specifically midways.

A rare gem in a vein of Big Entertainment (read: nestled within minutes of Disney World and Universal), Old Town Kissimmee offers affordable, traditional family fun which, once mainstream, now makes for a truly unique getaway. With classic rides, games, shops, snacks, and weekly events, Old Town will transport you to the heyday of American childhood.

With American Graffiti type nostalgia, Old Town Kissimmee seems to have cryogenically frozen time in order to preserve the best of lazy summers from the 50s and 60s. You’ll feel as if you’ve recaptured years gone by, or maybe find yourself nostalgic for an era you never personally experienced.

If you are wondering what to do in Old Town Kissimmee, we have you covered. Whether it’s a trip down memory lane or a completely new experience, Old Town is a delightful stop in the Orlando area for a date, family outing, or friendly get-together!

Happy Days Are Here Again

If you visit Old Town at dusk, you’ll be greeted by the glow of neon lights. Everything is veiled in vivid shades of pink, green, and blue.

The rides are the most spectacularly lit, like beacons of fun, beckoning everyone to come to have a good time. The Ferris Wheel is the brightest of all, standing over 85 feet tall and bedazzled with color-changing LED lights. Custom made in Italy, this one-of-a-kind attraction offers stunning views of the surrounding Orlando area.

There’s also a lovely carousel with gorgeous, prancing ponies—a timeless classic that’s fun for all ages—or you can get your kicks riding the Hurricane, a five-story tall roller coaster. And for those who don’t mind feeling dizzy, try out the Paratrooper; the ride cars dangle from a spinning wheel, rocking back and forth as the wheel turns forwards and backward!

Old Town Ferris Wheel and other rides light up the night.
Old Town Kissimmee lights up the night sky. (Photo: Experience Kissimmee via Flickr)

Old Town isn’t just made of up rides, though! Enjoy the midway-style attractions at Happy Days Family Fun Center, including an old favorite: skeeball! From video games to games of skill, there are over 50 ways to play and earn tickets that can be redeemed for prizes. If you’re up for a real challenge, you can test your aim at the Rootin & Tootin’s Shootin’ Alley, home of “Gater,” a talking 1949 International pick-up truck! (Hmm…does Gater seem familiar somehow, or is it just me??)

For a test of mind, body, and strength, you can also brave the Xtreme Ninja Challenge, conquering a course of daring obstacles and perilous traps. Only a true shinobi will pass this trial. Will you?

Eat, Drink, and Go Shopping!

While much of Old Town’s charm radiates from the carnival-style rides and games, a trip here just wouldn’t be complete without grabbing a bite to eat and popping into a shop or two. After all, what’s a town without a diner and a general store?

Of course, Old Town is much larger than your average “one-horse town” and has several yummy options for lunch and dinner! There are true classics like A&W burgers, Nathan’s Famous hotdogs, and Auntie Ann’s pretzels, but there are also more exotic options like Mr. Sushi, Downtown Deli that serves Greek gyros, and the Beef Jerky Experience! Whatever you may be craving, there’s something in Old Town to satisfy, and with a variety of sit-down and to-go options, you can even pick a place to match your pace!

Nathan's Famous on Coney Island.
Old Town has a Nathan’s Famous, just like Coney Island! (Photo: Unsplash)

Keep strolling down the brick-lined streets and explore the many shops Old Town has to offer, including Black Market Minerals where you can find crystals, fossils, and super cool salt rock lamps. There’s also woodcrafts and leather shop, as well as one store that specializes in magnets for livening up that old refrigerator! There are even internationally themed shops, with British Isle Connection offering everything from European chocolate to Doctor Who merch (score!), and Mini Queen, which specializes in Japanese merch from your favorite animes like Naruto (double score!).

If you’re looking for personalized memorabilia, there are caricature artists, a wax hand stand, custom embroidery, and an old-timey portrait gallery! Fun and unique, you’ll cherish these souvenirs almost as much as the memories you make in Old Town.

A Night On The Town

Old Town in Kissimmee is one of those places you can visit again and again. Not only are the rides and midway games timeless activities, but there are also weekly events to delight and entertain!

There’s live music on multiple nights throughout the week from various artists—usually locally based—whose performances range from country to pop to rock and roll. In addition to regularly scheduled live music, Old Town is also known for hosting some awesome car shows! Whether you want to bring your own shiny Studebaker or simply admire everyone else’s classic Chevys and Fords, Old Town Kissimmee car shows are just another way they keep the past alive in the present day. Shows take place every Saturday starting at 1:00 p.m., with other specially themed car shows also scheduled throughout the year.

59 Lark
Check out some true classics cruising around Old Town! (Photo: Unsplash)

The best part about all of this awesomeness in one place? Entry into Old Town is free. Want to watch live music? Free. Enter the Old Town Kissimmee car show? Free. Eating at the restaurants? Okay, you’ll pick up a bill there. But Old Town is still wonderfully affordable. Any money you spend at shops or on games is completely optional! So you can have a small budget and still have a great time!

Disney, Universal…you better watch out. When it comes to entertainment, Old Town—and old school—is the way to go!


Have you been to Old Town? What’s your favorite thing to do there? Let us know in the comments below, along with your highest skeeball score!

See you on the next adventure!

Cover Image

Photo: Unsplash

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