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Historic Downtown Kissimmee

Stroll the streets of Historic Downtown Kissimmee, Florida, and it’s easy to see why this quaint, all-American town has seen such a revival in recent years. While its start may have been rooted in cattle and citrus, this former shipping town is now better known for the boutique dining, one-off shops and lively nightlife scene that dot the city center along Main Street and Broadway.

Doing Dakin

The epicenter of downtown’s renaissance is Dakin Avenue, home to several great restaurants and chic bars. 3 Sisters Speakeasy sits at the corner of Dakin and Broadway and beckons hungry diners in for everything from savory pulled pork sandwiches to artful sushi rolls. Savion’s Place got the attention of celebrity chef Emeril Lagasse for its Caribbean cuisine with a twist. Willy’s Wieners, which boasts more than a dozen different dogs, is a great place for a quick bite. Vintage Vino, boasting more than 50 different wines and 35 craft beers, is a cozy spot to while away a few hours. Slip into the very chic Red Shoe Martini Bar to savor a martini, or drink a beer and shoot some pool at The Wicked Stepsister across the street—which kicks off each weekend with live music on Friday nights.

Bumper-to-Bumper Crops

Kissimmee Valley Farmers MarketBig events create a festive atmosphere in Historic Downtown Kissimmee year-round, but two repeating crowd pleasers deserve a special shout out. Kissimmee Lakefront Park is home to the weekly Kissimmee Valley Farmer’s Market, where several food-preneurs vend everything from seasonal produce and gourmet soup to fresh pasta and fancy soaps every Tuesday from 3 to 7 p.m. And on the first Friday of every month from 6 to 9 p.m., up to two dozen local food trucks descend on Dakin for the Food Truck Bazaar. Hundreds of hungry patrons enjoy unique meals on wheels as they stroll along the bricked avenue. Craving chicken and waffles or Korean BBQ tacos? The Bazaar has that covered, plus plenty of sweets to rev your engine. See what events are happening during your visit.

Lakefront Park

Monument of StatesAlso on Friday nights (are you sensing a theme?), families head to Lakefront Park for the monthly outdoor movie screening beginning at dusk. This 25-acre park, perched on the shores Lake Tohopekaliga (a.k.a. Lake Toho), is also where visitors find the legendary Monument of States, a 50-foot tower made with blocks of granite, chunks of quartz, small boulders, fossils, and pieces of old buildings from all over the country. There’s also a huge playground for kids and a three-mile paved trail that skirts the water and sees a steady stream of walkers, joggers, bikers and fishers. Check out other popular nature trails in the area.

Shop Around

Antique ShoppingDowntown houses many charming independent boutiques, including several galleries and antique shops that are worth a wander through. Shoppers can find a bevy of bygone trinkets at Echoes of Yesterday and even more at Lanier's Historic Downtown Marketplace, an 18,000 square-foot antique mall packed full of kitschy collectibles. Gallery One Artists, Osceola County’s largest art gallery, operates as a co-op and showcases the work of more than 20 local artists. Find more on these and other popular shopping spots in the area.


One way to peel back downtown’s layers is via a self-guided walking tour, available for pick-up at the Kissimmee Main Street office (421 Broadway). In addition to highlighting the area’s many landmarks, the Kissimmee Sculpture Experience also guides visitors to fine-art sculptures spread throughout downtown and the lakefront area. Those interested in the area’s eerie side might consider reserving a spot on the Kissimmee Ghost Tour, which takes attendees on a thrilling 90-minute stroll. Don’t be surprised to experience goose bumps on this spooky, starlit tour as guides spin tales of the murder and mayhem in Kissimmee’s illustrious past.

Make sure your Florida vacation includes a visit to Historic Downtown Kissimmee. Find the perfect accommodations in the heart of Kissimmee, Disney and Orlando attractions.

See all Things to Do.

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