Old Town Kissimmee

Old Town Kissimmee

It’s been a part of the Kissimmee landscape since 1986, and it has undergone several major refurbishments, but the iconic Old Town shopping and entertainment district is still providing new excitement for guests 36 years after its debut.

For regular visitors, it’s easy to forget that Old Town was one of the primary trailblazers along Highway 192. So much is new, especially on the western stretch of this 25-plus-mile tourist corridor, that the originals tend to get overlooked.

Its re-creation of a classic Florida town with distinctive storefronts, period architecture and brick-lined streets is hard to discern from the highway (although the 86-foot-high Ferris Wheel at its entrance is hard to miss!), but it is well worth turning off by Marker 9 to rediscover it.

(First time visitors – you should definitely have this on your radar, along with the amusement park of Fun Spot next door)

What’s There

Just to start with, Old Town boasts more than 60 unique shops and themed restaurants and bars, as well as a sprinkling of family-friendly attractions. Some names will be familiar, such as Flipper’s Pizzeria and Nathan’s Famous hot dogs, but many will be new.

That’s enough to keep most visitors amused for several hours, and there is a distinct party vibe in the evening, when the bars kick into high gear and there is live entertainment on the Trophy Row stage most nights.

The entertainment elements vary from a traditional carousel ride, small-scale roller-coaster and iconic Ferris Wheel to a walk-through haunted house, Mortem Manor, Good Times Escape Room and live shows periodically at the Great Magic Hall.

Then there are the weekly live events, including karaoke, local bands and the Saturday ‘main event’ of the Classic Car Show & Cruise, which is a must-see for every Orlando visitor. Parking is also free, which is another bonus, although it is quite limited so get there early if you can.

Where can I stay near Old Town Kissimmee?

Luckily Debbie’s Villas has over 200 (that’s two hundred!) villas within a few minutes of Kissimmee Old Town – so you can pretty much take your pick for all party sizes and budgets.

Best Shopping

While there is a tendency for some shops to come and go, there is still a terrific array of one-of-a-kind stores that are worth perusing for all manner of souvenirs and knick-knacks.

Chief among them are the Extreme Woodcrafts Gift Shop, the fancy goods of Old Town Leather, costume jewellery at Gold Hut, and the nautical apparel and gifts of Salty’s.

Need sunglasses? Head for Shades in the Sun, while Skully’s Rock ’n Roll Experience has a dazzling array of rock and pop memorabilia. Then there’s Teams for a super selection of American sportswear and Tiki Jim’s for a wonderful choice of novelty T-shirts, hats and gifts.

And don’t miss the all-round retro style of the Old Town General Store, with its speciality apparel and throwback souvenirs. It’s kitschy as heck, but you’re on holiday, right, and you want to see candy piled up in barrels and masses of Coca-Cola mementoes, don’t you!

Best Dining & Bars

If you’re just looking to graze, this is definitely the place to come as there are a dozen grab-and-go options that allow you to chew as you wander, from Sweet Dreams Ice Cream Café and Kissimmee Popcorn to Mr Sushi and Auntie Anne’s, which deals in a wide variety of pretzel type snacks.

For that typical all-American experience, seek out A&W for its signature burgers, hotdogs, and sweet treats, including a fab root beer float, which has to be sampled at least once.

If it’s an alcoholic beverage you are after, step back in time at Bobby’s Garage Bar, which serves a wide variety of domestic craft beers, opt for the more cocktail orientated Southern Breeze, or try something completely different at Sakeba Asian Pub & Grill.

Staying for the evening? Be sure to join the party at Sun On The Beach, where it’s 80s night on Fridays, Top 40 Night on Saturdays and Latin Night on Sundays.

Classic Car Parade at Old Town Kissimmee

Perhaps more than anything, though, Old Town is best known for its classic car parades, a tradition that has been going since its early days and is billed as the longest running weekly car show and cruise in America.

Typically, the Wednesday Night Themed Car Show is a unique display featuring show-quality specific types, models or makes of cars and trucks, with the show beginning at 5pm and live music on the Trophy Row stage from 6pm. It is free for visitors and owners alike.

Fridays is the turn of the Muscle Car Show & Cruise, with a line-up and parade of show-quality muscle and factory-performance cars of 1960s vintage and newer classics from the 1980s. The cruise begins at 8.30 and, once again, there is no fee for just coming in to watch.

Finally, the granddaddy of them all, which recently celebrated its 32nd anniversary, is the Saturday Classic Car Show & Cruise, which brings in the crowds from 1pm, when this ever-changing display of pre-1985 hot rods and other models is on show, with a main parade through the central streets at 8.30pm.

The Classic Car Show is a true one-off in local entertainment terms, and it remains as bright and compelling today as it did when it started in 1990. And, unless you go crazy in Old Town’s gift shops, any visit here won’t break the bank!

For more details, visit myoldtownusa.com.

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