Walk into Kissimmee’s Old Town and banners hanging from lampposts convey the vibes of its groovy scene: 40 Years of Quirky Cool.
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The retro-themed, open-air entertainment and shopping district in the heart of the city’s tourism corridor is centered around a brick-covered boulevard lined with dozens of shops, restaurants and bars — many unique to Old Town — boasting facades and architecture evoking decades long past.
But now, it’s the future of the the 18-acre site that’s on everybody’s mind.
Todd and Radha Rambilas, owners of RS Equity Services of Orlando, bought Old Town for $24.5 million in September. They own and manage several commercial properties across the Orlando area.
Radha Rambilas said Friday by email that they want Old Town to remain a welcoming destination for everyone while evolving through thoughtful improvements, engaging events and a stronger connection to the broader Central Florida community,
One idea is for a recurring calendar of annual happenings that celebrates the diverse cultures and traditions throughout Central Florida, she said. Under consideration are celebrations inspired by Diwali, Holi and Caribbean holiday traditions that feature authentic cuisine, music, local vendors and family-friendly activities.
“Our goal is to create opportunities for local businesses, artisans and cultural organizations to showcase their traditions while introducing visitors to new experiences, Rambilas said.
On one recent weekday, the throwback theme was established throughout Old Town by a soundtrack of hits from the likes of David Seville (“Witch Doctor” from 1958), Lesley Gore (“Judy’s Turn to Cry” from 1963) and The Chiffons (“One Fine Day” from 1963).
It’s a perfect fit for Wound ‘N Around, a store that sells reproductions of memorabilia from the 40s, 50s and 60s — including items with Marilyn Monroe, Elvis Presley, The Beatles, Betty Boop, John Wayne, “The Wizard of Oz,” “Gone with the Wind,” “I Love Lucy,” “Star Wars,” classic TV shows and much more.
Cheryl Hill and her late husband, Ernest, opened the store in December 1986. She said the name was a play on words tied to vinyl records.
“We were here since Day 1,” Hill said. “I love it, it’s in my heart.”
The interior features a checkered tile floor; a larger-than-life Monroe statue showing the iconic moment when a draft blew her dress up while filming “The Seven Year Itch” in 1954; and the shell of a teal 1962 Chevy Impala that was found in a junkyard and restored.
Hill said the couple were traveling through the area in the mid-80s and saw Old Town under construction. After that they went home to Massachusetts, quit their jobs working for utility companies, “sold everything but our kids” and moved to Florida, she said.
“We came down, we didn’t know what we were doing, all we knew was that we loved the look of Old Town,” she said.
The Hills’ first store was about 775 square feet — slightly smaller than a typical single-family home built in the 1950s. Two moves and four decades later it’s about 2,500 square feet — close to the average size of a newly built single-family home today.
Although Hill hasn’t met or talked with the new owners, she’s optimistic they’ll do good things for Old Town — which she said could use a facelift.
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The Los Angeles-based The Travel Corp., the property’s previous owner, did invest $20 million in improvements when it bought the site in 2014, including an 86-foot-tall Italian-crafted Ferris wheel and the center’s iconic jukebox-themed entry sign.
Other attractions include an arcade, virtual reality arena and a walk-through haunted house. Neighboring Fun Spot America also has a roller coaster, Tilt-A-Whirl, carousel and Scrambler.
New shops and restaurants were added in 2020, bringing the total size of the center to 132,000 square feet.
And despite competition from nearby attractions like Disney World, Hill said it’s the car shows that set it apart. The weekly events, a popular fixture for decades, lure such sizable crowds that she’s seen people arrive and then drive off because they can’t find a place to park.
On Friday nights it’s the Muscle Car Show & Cruise and on Saturday nights it’s the Classic Car Show & Cruise. Wednesday nights are for the Bike Show that features all makes and models of touring motorcycles, Harleys, Indians, trikes and Slingshots (think a three-wheeled open-air Roadster).
Just down the street from Hill is Faux Paws Dog Shop boutique, where Julie Ferreira has been manager since it first opened in 2024. But her own history with Old Town goes back much further than that.
Back in the early to mid-90s, when she was around 20 years old, Old Town was the place to go.
“Disney Springs wasn’t there, it was Pleasure Island back then,” Ferreira said. “So after dark, or when it closed over at Disney, this is where everybody came. You just walked Old Town and it was fun.”
The pet boutique specializes in unique gifts, dog accessories, American-made treats and custom pup apparel. Ferreira described it as a canine-focused version of Spencer’s, the novelty retail chain.
She said she hasn’t met the new owners either, but sees the sale as a positive because the Rambilas are a local family and Old Town is in a great location with lots of potential.
“A lot of locals come just to hang out because it’s kind of a quiet spot, as you can see, on certain days of the week, and we’d love to have that turned around,” Ferreira said. “But we get a lot of returns … you have generations that have been coming here that come every year, no matter what.”
Among those who keep coming to Old Town is Karen Matthews, who said she’s from Alabama and Georgia, and has fond memories of annual visits stretching back decades.
“The food is good, the kids love going in the different shops,” she said. “My grandchildren and my great-grandchildren now come. The kids love the rides — grandma not so much.”
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