St. Augustine: Saint George main street on sunny day in downtown, via Kristi Blokhin / Shutterstock.com

7 Towns in Florida With Thriving Local Businesses

While shopping, dining, and indulging in franchise businesses has become a way of life for most, there are so many benefits to supporting local businesses. From reducing your carbon footprint to stimulating local economies, there is truly no better way to support the American Dream and give back to a community.

Beyond these important advantages, there is also much to be said about the sheer enjoyment that comes with exploring local businesses. Whether tasting generational recipes at a family-owned restaurant, hunting for treasures from a different era at an antique shop, or enjoying a cappuccino steamed with love at a local cafe, the experiences are so much more soulful and reminiscent of simpler times.

If you are looking to support more small business owners in 2024, here are 7 Florida towns whose thriving local businesses will inspire you to embrace authenticity. From adorable mom-and-pop restaurants to one-of-a-kind shops and attractions, the more you embrace local businesses, the more you help keep these vibrant communities alive.

Winter Park

Retail stores on South Park Avenue in downtown Winter Park, Florida.
Retail stores on South Park Avenue in downtown Winter Park, Florida.

Just north of Orlando, the charming town of Winter Park blossomed as a resort community in the late 1800’s. Today, the town continues to thrive thanks to its main outdoor attraction, the Winter Park Chain of Lakes—a series of 6 stunning bodies connected by canals. But beyond these stunning scenes, Winter Park is equally beloved for its one-of-a-kind businesses and spirited downtown. Park Avenue alone is home to over 140 local cafes, restaurants, boutiques, and museums.

For your first stop on Park Avenue, George’s Cafe is an adorable family-owned establishment that has served the community for over 30 years. Pop in for a coffee or one of their gourmet cookies before you take on the rest of what Park Avenue has to offer. Right next door, you will find Antiques On The Avenue, an independent antiques shop with everything from artwork to jewelry and so much more.

Also nearby, you will find the Tiffany Light Museum, the Sultre Boutique, and for book lovers, the Writer’s Block Bookstore. With a mission “to be a destination for those who love that small, locally owned bookstore,” the Writer’s Block Bookstore is the perfect place to support a local business and stock up on a year’s worth of reading material.

Dunedin

Urban views on Douglas Ave in Dunedin, Florida
Urban views on Douglas Ave in Dunedin, Florida

Similar to Winter Park, the town of Dunedin pairs beautiful outdoor scenes with a dazzling commercial district. And even if you come for the white-sand beaches or scenic paths in this designated trail town, no visit would be complete before checking out Dunedin’s adorable Main Street. The walkable, palm tree-lined stretch makes for a super relaxing evening of window shopping and sampling.

After a day in the sand or adventuring Dunedin’s trails, what could be better than a refreshing artisan beer? The Dunedin Brewery, famous for being Florida’s oldest microbrewery, also has a nationally acclaimed music venue and some of the best bar food around. For a sweet treat, the Dunedin Coffee Company & Bakery is a great follow-up, or you could grab a drink or snack at the family-owned Mangos and Marley: A Coastal Cafe.

If you visit Dunedin on a Friday or Saturday, the Downtown Market in Pioneer Park is another must, with tons of stalls and vendors. Selling everything from fresh produce to artisan dog treats, whether you shop for yourself or your furry friends, the market is a ton of fun to browse and a great way to support local businesses. But if you are not in town on a market day, have no fear—there are still plenty of local businesses on Main Street, including Nancy’s Fancy boutique, the My Favorite Things gift shop, and the Clay and Paper Gallery of Art to name a few.

Safety Harbor

Safety Harbor Florida downtown on the west shore of Tampa Bay
Safety Harbor Florida downtown on the west shore of Tampa Bay, via Linda White Wolf / Shutterstock.com

Just a short drive from Dunedin along the western shore of Tampa Bay, Safety Harbor’s charming downtown transports visitors to simpler times. Shaded by towering oaks, the brick-paved Main Street is a comfortable and charming stroll, providing that quintessential small town feel. Some popular local highlights include the Syd Entel Galleries, Sips Wine Bar, and Portkey Books, a cozy independent bookstore. Also noteworthy, is Cafe Vino Tinto, a specialty coffee shop that sources their coffee right from their own Costa Rica farm.

If planning your visit in advance, you can also experience Safety Harbor’s Main Street Festival, held on the third Friday of every month. Featuring food stalls, live music, and dozens of local vendors, the festival is a fun experience for the whole family and a great one-stop place to shop for gifts. Additionally, the Safety Harbor Farmers Market is open every Sunday from 10am to 3pm at John Wilson Park, offering local produce and handmade goods.

St. Augustine

People shopping in St. George Street in Saint Augustine, Florida
People shopping in St. George Street in Saint Augustine, Florida, via Andriy Blokhin / Shutterstock.com

For a town with endless historic charms and some truly unique businesses, visit St. Augustine, the "Nation’s Oldest City.” Founded in 1565 by Don Pedro Menendez de Aviles, St. Augustine boasts structures dating back to the 1600’s. Over on St. George Street, the town’s original main street, visitors can venture back in time to Spanish Colonial times while appreciating some of St. Augustine’s coolest businesses and attractions.

As a pedestrian-only road, St. George Street is especially easy to explore by foot. Adults will appreciate bars like Prohibition Kitchen, a retro-chic gastropub with live entertainment and refreshing cocktails, while families can count on delicious eats at MiMi’s Famous Crepes. For thrifty shoppers, businesses like Vintage Clothing Co. are a great next stop, while the St. George Souvenir Shoppe is a nice choice for a memento. Finally, if you head just off this main strip, St. Augustine has some really cool local attractions that the kids will enjoy, like the famous Shipwreck Museum or Pirate & Treasure Museum.

Tarpon Springs

People walking around in the historical downtown of Tarpon Springs, Florida
People walking around in the historical downtown of Tarpon Springs, Florida. Image credit Microfile.org via Shutterstock.com

Over on Florida’s Gulf Coast, Historic Downtown Tarpon Springs is a gateway to more unique historic attractions, along with a wide range of mom-and-pop shops, restaurants, and cafes. Encompassing 700 acres, the area features 145 historic buildings, earning it a place on the US National Register of Historic Places.

Many of the district’s businesses are located in these significant historic structures, including gems like The Bayou Cafe. Housed in a building that once served as a cigar shop and pool room back in 1910, the restaurant is a great place to get classic American food for breakfast, lunch, or dinner. Other downtown focal points include restaurants like the Tarpon Tavern, antique shops like Bear Haven Land Company Vintage Toys, galleries like the Tarpon Art Guild, and metaphysical gift shops like The Healing Hedge Witch.

Micanopy

Historic downtown Micanopy, near Gainesville, Florida.
Historic downtown Micanopy, near Gainesville, Florida.

If searching for antique treasures is your idea of a good time, the quaint town of Micanopy is your ticket to bliss. Despite having less-than-700 residents, this tiny town is a goldmine for antiquing enthusiasts. The Micanopy Trading Outpost, Delectable Collectables, and the Shady Oak Gallery are just a few local antique shops worth noting, while the Antique City Mall is arguably the most popular.

Elsewhere in town, visitors can experience that sweet southern hospitality at local hotspots like the Old Florida Cafe and Pearl Country Store & Barbecue. For a more rural local business, the Mosswood Bakehouse is a delightful woman-opened, family-operated artisan bakery housed in a historic farmhouse.

Cocoa

The sign welcoming visitors to the historical Cocoa Village.
The sign welcoming visitors to the historical Cocoa Village. Editorial credit: Beachside Tribe / Shutterstock.com

Finally, we have the off-the-beaten-path town of Cocoa, whose adorably-named Cocoa Village is as pleasant as it sounds. Perched on the Indian river, this historic Florida neighborhood is all about promoting local businesses, so there are many to see and explore. For tasty eats, places like the Ossorio Bakery & Cafe sell everything from french pastries to flatbread pizzas or you can get a sweet treat at Sweet Caroline’s Village Ice Cream, a family-owned shop offering over 30 flavors since 1975.

For the kids and young at heart, the Antilles Trading Company Maritime Pirate Museum and Store is another fun Cocoa Village attraction. It is also a brief walk from tons of other cute businesses, like the Hello Again Bookstore, a woman-owned, LGBTQ+ independent bookstore selling new and used books for people of all ages. Right next door, you can hunt for vintage and new treasures at businesses like the Treasure Hunters Mall, Space Coast Records, and a bit further down, the Stone Street Apothecary and Antique Marketplace.

Final Thoughts

Although we often gravitate towards franchise stores and restaurants out of necessity or convenience, there are numerous advantages to be gained from supporting local businesses. Whether you aim to invigorate a local economy or simply desire a more soulful small-town experience, these 7 Florida towns and their local businesses offer the perfect blend of both. From Dunedin's eclectic downtown markets to Micanopy's impressive array of antique shops, these flourishing local spots will not only delight, but may just inspire you to incorporate more small businesses into your daily routine.

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