10 Most Historic Small Towns to Visit in Florida in 2024 (2024)

Florida is mostly known as a place of irresistible islands and beaches, amusem*nt parks, and interesting wildlife. While these are great features of the state, they often push its historic allure to the back seat. Meanwhile, Florida packs a sizable chunk of America’s history, and that alone is worth getting on the next flight to the Sunshine State. While the big cities have their share of the state’s history, the small towns preserve the larger chunk. For instance, St. Augustine - one of the state’s small towns, is the oldest continuously inhabited European settlement in America, founded in 1565. Several other small towns like the aforementioned are spread out across the state’s islands and keys, awaiting to satisfy history enthusiasts. Without further ado, here are the 10 most historic towns to visit in Florida.

Madison

Madison was first settled in 1838 and developed as a cotton plantation. Over the years, it has become a bustling town, and today, it hosts attractions like the Treasures of Madison County Museum, where visitors can discover its iconic past via various exhibits and tours. The downtown area is also a great place to just walk through and see historic buildings from the 19th century. The Wardlaw-Smith House is another stunning attraction history buffs would love as it features Greek Revival architecture and dates from 1860. While in town, don’t miss out on the Four Freedom Park (dedicated to a resident recognized as the first US hero of World War II). Before leaving, shop antique items at Madison Antiques Market & Interiors, and when hungry, get filled at Grumpy’s Diner on Main with outdoor seating.

Cedar Key

Cedar Key is an island town in Levy County, with a human history dating to 500 BC. However, the area rose to prominence in the early 1840s when it became involved in the Seminole War by hosting a US military base. By 1842, the battle was over, and the town was settled, which soon became a major shipping port. Today, one can learn more about the town’s history, including its role in several wars, at the Cedar Key Museum State Park. Also, check out the Island Hotel, which opened in the 1850s and is still operational. Afterward, head to the Cedar Key Pier to fish and also enjoy boating, kayaking, and canoeing in the surrounding waters. Before leaving, enjoy a delectable plate of seafood at Tony’s Restaurant.

Micanopy

Micanopy, Florida's oldest inland town, is as historic as they come, and even its motto reads “The Town That Time Forgot.” This town’s history dates back to 1823, when it became the first official town in the US after Spain ceded Florida to the US in 1821. While visiting today, start by exploring some historic structures at the Micanopy Historic District, which indeed seems to have been forgotten by time. Some top draws to admire in this area include the Church of the Mediator (1874), Herlong Mansion (now a bed and breakfast), and Simonton House (1910). For a more detailed look into the town’s history, head to the Micanopy Historical Society Museum and then visit the Micanopy Historic Cemetery, which dates back to the early 1800s. Afterward, shop for antiques at Delectable Collectibles and Antique City Mall, then dine at Old Florida Café.

Apalachicola

Apalachicola is one of the lesser-known destinations in Florida with an interesting history and lots of opportunities for outdoor recreation. While evidence of human inhabitation dates to 2,000 BC, the area came into the spotlight in the 1700s when it became a Spanish territory. By 1821, Florida was officially ceded to the US, and seven years later, in 1828, the town was incorporated as West Point until 1831, when it was renamed Apalachicola. As early as 1837, the Trinity Episcopal Church was established as the first church in the town, and it still serves worshippers today. The Raney House is another early structure in town first built in 1838. Visit these historic structures and then head to John Gorrie Museum State Park to explore the inventions of a local physician, like air conditioning for early yellow fever patients. Enjoy more history at the 19th-century Orman House Historic State Park and catch a fascinating show afterward at Dixie Theatre. For outdoor adventures, head to Apalachicola River to enjoy fishing, boating, kayaking, and canoeing.

Monticello

Monticello is the county seat of Jefferson County and was named after Thomas Jefferson’s home in Virginia. The town was first laid out in 1827, and today, it is home to several historic landmarks. It is famous for being a sleepy town without a single traffic light. Some top historical allures worth checking out here include the Jefferson County Courthouse (1909), Monticello Old Jail Museum (1909), and Christ Episcopal Church (1885). The town also hosts Perkins Opera House, built in 1890 and still functional for shows, musicals, and theatric performances. Art lovers can explore the Jefferson Art Gallery and be stunned by the mind-blowing creativity on display.

Fernandina Beach

Fernandina Beach is a historic town in Amelia Island renowned as the “Isle of Eight Flags” owing to the various countries such as Spain, France, and Britain that once colonized it. It was named after King Ferdinand VII of Spain and is considered the birthplace of the modern shrimp-fishing industry. While in the town today, grace Fort Clinch State Park to witness civil war reenactments, relax at a beach, fish, hike, and surf. Afterward, admire Amelia Island Lighthouse, the oldest in Florida, and also visit the Amelia Island Museum of History for a detailed look into the iconic natural and human history of the entire island. Recline afterward at the Amelia Community Theatre to enjoy scintillating shows and performances, and don’t forget to dine at the Down Under Restaurant.

Mount Dora

Mount Dora is a beautiful small town full of Southern charms and fascinating history. The town was founded in 1874 when David Simpson and his family settled in the area, and today, visitors are invited to Mount Dora History Museum to learn more about the past via exhibits. Head to the town’s historic district to see iconic structures like the Donnelly House and Lakeside Inn, one of the oldest hotels in Florida. Don’t forget to visit Grantham Point afterward to see Florida’s only freshwater lighthouse. Stop by the Mount Dora Center for the Arts and be blown away by its astonishing galleries and sculptures. Before leaving, kick back at Lake Dora to enjoy a pontoon boat tour or stroll on the boardwalk for scenic views.

Brooksville

The history of Brooksville began as a fort and trading post in 1840 but was first settled by four families in 1845. In 1856, the town was established officially following the merger of Melendez and Pierceville towns. Once here, immerse in the town’s history at the 1885 Brooksville Train Depot and Railroad Museum. Next, visit May Stringer House, which houses the Hernando Heritage Museum, where exhibit rooms and over 10,000 artifacts reflect the county’s roots. Also, check out the Hernando County Courthouse, built in 1913, and William Sherman Jennings House (1890). Art lovers can embark on the Brooksville Arts and Mural Tour to explore the town’s numerous murals. When hungry, they can recline at the Chop Block Grill to savor finger-licking delights.

Key West

The island of Key West sits at the southernmost point of the American Continent and features a history dating back to the 1700s when the area moved from Spanish rule to British and then US rule. Several years after, in the 1820s, settlement began in the area, and these days, the town boasts enchanting scenery and a host of historic attractions. For starters, admire the concrete Southernmost Point Buoy at 18 feet above sea level, marking the southernmost point in the Continental US. Next, visit the elegant Key West Lighthouse and the majestic Ernest Hemingway House, the home and museum of a renowned American Writer. Fort Zachary Taylor Historic Park is another history hot spot by the ocean to explore, with nature trails and a pre-civil war fortress. Afterward, hit the town’s most famous avenue, Duval Street, to enjoy lunch at Seaside Café at the Mansion in an outdoor setting.

St. Augustine

St. Augustine is the oldest founded town in the contiguous United States, established in 1565 by Spanish explorers. Hence, the town served as the capital of Spanish Florida for over 200 years until Spain officially ceded Florida to the US in 1821, and it also became one of the two capitals of Florida Territory afterward. Today, history shines at every turn in the town, and visitors can start with the Castillo De San Marcos National Monument, the oldest stone fort in the US, built between 1672 and 1695. Proceed to admire the St. Augustine Lighthouse, explore its maritime museum, and visit the Lightner Museum to see antiques dating back to the Gilded Age. Also, visit the St. Augustine Pirates and Treasure Museum to learn about pirate activities and see their artifacts. Don’t leave town without some outdoor adventures at Anastasia State Park and a taste of exotic wines at San Sebastian Winery.

Florida is one of the best states in the US to go back in time because of its rich history that combines effortlessly with dazzling ocean scenery. Step into its small towns to explore fascinating histories and tales of events that shaped the present world. From the southernmost point of the continent in Key West to the oldest town in the contiguous United States, history awaits every traveler in these small towns in Florida.

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