9 Unique Local Shops In Florida With History

Someone once told me the best way to know a place is to poke around its oldest shops, the kind where time slows and the cashier actually wants to chat. I believed them. Florida, under its sunburned postcards and chain-store glare, hides treasures – spaces worn by real life, not Instagram filters.

These quirky shops don’t just sell stuff; they hold stories, splinters, and a stubborn refusal to be boring. Ready for some honest-to-goodness Florida weirdness? Here are nine local shops with history that know exactly who they are (even if no one else does).

1. Richloam General Store

The Richloam General Store in Webster first opened in 1928 after an earlier store was destroyed by fire. For decades it served as a gathering point with a post office and even a railroad express stop. The store is listed on the National Register of Historic Places and is carefully preserved by the family that owns it. Visitors today will find shelves of jams, candies, and preserves that keep its tradition alive.

The wooden floors and original counters remain in place, giving the feeling of stepping back nearly a century. It is one of the few shops in Florida where the setting tells as much of a story as the goods. The store continues to connect the present with the past in an authentic way.

2. Bradley’s Country Store

Bradley’s Country Store near Tallahassee is another stop full of history and flavor. The store was built in 1927, though sausage making on the site began around 1910 when the Bradley family first sold it from their home. It has grown into a full complex that includes a smokehouse, a commissary, and a grist mill. The site was placed on the National Register of Historic Places in 1984.

Today visitors can buy Bradley’s famous smoked sausage, stone ground grits, and cane syrup. The shop is still family run and maintains many original features. People come for the food but also for the sense of continuity across generations.

3. Ted Smallwood Store

The Ted Smallwood Store in Chokoloskee is one of the most important historic trading posts in Florida. The store was built in 1917 by Ted Smallwood and also served as the community’s post office. It became a central place where local settlers and Seminole people traded goods. The building is raised on stilts over the water, which has helped it survive for more than a century.

It was listed on the National Register of Historic Places in 1974. In 1990 the store was reopened as a museum by Smallwood’s granddaughter and still displays original artifacts. Many visitors also learn the tale of the outlaw Ed Watson, which has become part of the store’s lore.

4. Rain Barrel Village

Rain Barrel Village in Islamorada is a lively collection of artist studios and shops in the Florida Keys. The most famous feature is the giant outdoor lobster sculpture that welcomes guests at the entrance. Visitors can walk through colorful paths filled with pottery, jewelry, paintings, and island crafts. It has become a popular stop for tourists driving the Overseas Highway.

Each shop is individually run, giving the village an eclectic character. While not historic in the same way as old trading posts, it represents Florida’s ongoing creative spirit. Travelers enjoy browsing for one of a kind items while soaking in the Keys atmosphere.

5. Walgreen Drug Store (Miami)

Downtown Miami is home to the historic Walgreens building completed in 1936. It was one of the early large pharmacies in the city and is designed in a streamlined Art Deco style. Its glass block and curved corners make it a standout among the downtown skyline. The building avoided demolition and has since been repurposed.

Today it houses Julia and Henry’s Food Hall, where visitors can find a wide variety of dining options. The food hall preserves the bones of the old Walgreens while giving it a new purpose. Architecture fans and food lovers both find reasons to explore this space.

6. Old Town Kissimmee

Old Town in Kissimmee opened in 1986 as a retro styled entertainment and shopping district. It features more than seventy shops, restaurants, and attractions in an open air setting. Classic car shows and themed events are held regularly, adding to its nostalgic charm. The district includes rides such as a Ferris wheel and offers live entertainment throughout the week.

Old Town has positioned itself as a playful alternative to the region’s large theme parks. The architecture and design deliberately echo earlier decades of Florida leisure. Many families return year after year to enjoy its mix of shopping and old fashioned fun.

7. Baker Block Museum

The Baker Block Museum in Okaloosa County preserves the history of Florida’s panhandle. Its exhibits cover agriculture, genealogy, military service, and community life. The museum includes a heritage park with structures such as a log cabin, corn crib, blacksmith shop, and post office. Each building was relocated to the site to give a fuller picture of early settlement life.

Admission is free, which makes it a welcoming place for anyone interested in local history. Volunteers help interpret the exhibits and share stories about the region. It is a small museum with a surprisingly wide range of artifacts and buildings.

8. Eola General

Eola General is a café and market located in the Lake Eola Heights neighborhood of Orlando. While not historic in the sense of being over a century old, it has become a neighborhood hub. The store offers coffee, bagels, sandwiches, and local products in a casual setting. Residents often gather here before heading to the nearby park.

Its charm comes from blending a café atmosphere with the feel of a small community store. Customers leave notes on a community chalkboard and frequently run into friends. It is a modern shop that emphasizes connection and local flavor.

9. Micanopy Historic Downtown

Micanopy is recognized as one of Florida’s oldest inland towns, incorporated in the 19th century. Its historic downtown is shaded by live oaks draped in Spanish moss. Antique shops and art galleries line the main street, giving visitors hours of browsing. The Micanopy Historical Society Museum displays documents, artifacts, and photographs about the town’s past.

Hollywood has even used Micanopy as a filming location, most famously for the movie Doc Hollywood in 1991. The town is known for its quiet atmosphere and historic preservation. Visitors often come away with both a souvenir and a sense of old Florida charm.