Florida is an interesting place, with a very interesting history. It makes sense that some of the best places in our state are the charming and historic towns, especially the oldest ones. It’s difficult to pin down the oldest places in the state, because so many of our towns predate Florida as a state, or even as a U.S. territory. We settled on using the official date of incorporation to help us find the 10 oldest towns in Florida, but it’s all open to interpretation. These towns also happen to be great places to visit. Here are 1o of the oldest towns in Florida (not listed in any particular order):

1. Micanopy
www.wikipedia.org
This small town just south of Gainesville is known for its historic buildings and great antique stores. It was incorporated in 1837, but its roots go all the way back before Florida became a U.S. territory. Nicknamed "The Town That Time Forgot," the history behind Micanopy is truly fascinating.
2. Jacksonville
Flickr/DeusXFlorida
Florida's largest city is also one of its oldest. Soon after Spain gave up Florida to the United States, folks near the area the British had called Cowford started founding this town named after Andrew Jackson. It was officially incorporated in 1832. From hiking trails to beautiful beaches, Jacksonville appeals to just about everyone.
3. Apalachicola
Flickr/Judy Baxter
This town of around 2.200 in the Panhandle was originally incorporated as the town of West Point in 1827, and then became Apalachicola in 1831. It's famous for its small town charm and excellent oysters.
4. Quincy
Flickr/Jimmy Emerson, DVM
This town in Gadsden County was established in 1828, named for our sixth president, John Quincy Adams. In its early years Quincy became very prosperous due to a booming tobacco industry.
5. Key West
Flickr/clarkmaxwell
Lt. Commander Matthew C. Perry planted an American flag on Key West in 1822, claiming the islands for the United States, and it was incorporated as a city in Florida in 1828. Head to the Key West Historic District, or Old Town, to see some of the oldest structures on the island.

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6. Tallahassee
Flickr/Stephen Nakatani
Tallahassee was incorporated in 1825. It was chosen as the capital of Florida long before Florida became a state, due to its central location between Pensacola and St. Augustine.
7. Marianna
Flickr/Jimmy Emerson, DVM
Marianna was founded in 1828, and named for the Scottish founder's wife Mary and her friend Anna. Marianna's downtown has a nicely restored historic district, and it has been recognized as a Florida Main Street Town.
8. Fernandina Beach
Flickr/Steven Martin
The "Isle of 8 Flags" may have been controlled by eight different nations, but it's been an incorporated town here since 1825. The history of this city in Northeast Florida goes much, much farther back. Many of the 19th-century buildings remain in the charming downtown district..
9. Pensacola
Colin Hackley via Flickr/VISIT FLORIDA
Pensacola is one of the oldest and most historic cities in America, with a settlement that predated even St. Augustine's (but only lasted a short time). Pensacola became part of the U.S. in 1821, and it was officially incorporated in 1825. Its history far predates this time, and it was ruled by five different flags in its history.
10. St. Augustine
Flickr/Steven Martin
The oldest continuously inhabited city in the United States, St. Augustine retains a lot of its historic charm, while continuing to evolve and grow. It also served as the capital of Spanish Florida, and of U.S. Territory of Florida before it was changed to Tallahassee. As with many old cities, there's several ghost stories swirling around St. Augustine, including haunted hotels like the Casablanca Inn On The Bay.

Have you been to any of these historic towns? Does your town have a lot of fascinating history? Please share it with us!

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Oldest Towns In Florida

Jackie Ann | May 07, 2021

What are the most charming small towns in Florida?

If you are looking to get away from the hustle and bustle of the big city, the Sunshine state offers a number of destinations bursting with friendly small-town charm. Located off Florida’s peninsula on the Gulf of Mexico, Sanibel Island is an idyllic spot to spend a relaxing seaside weekend. The island’s reputation for amazing sunsets and world-class luxury resorts has made it a popular vacation area for locals and tourists alike. Dreamy beach views and crystalline waters create the perfect backdrop for the multitude of vacation activities available. Spend a sunny day fishing, snorkeling, boating or just wandering the sandy shores hunting for the perfect seashell.

What is the most unique town in Florida?

Located just north of Tallahassee is the unique little town of Havana, voted as the Friendliest Small Town in Florida. Havana boasts a long and fascinating history originating in the first eras of Florida’s development and later thrived with the production of shade tobacco during the early part of the 1900s. After the major tobacco crops dwindled, the town became known as a notable shopping destination among treasure hunters who began frequenting the village’s specialty antique shops and galleries. Art lovers will enjoy perusing the work of both local and national artists at the Gadsden Arts Center in the Quincy Historic District.

What is the most naturally beautiful town in Florida?

Florida’s gorgeous natural landscapes and unique regional terrain make for some truly beautiful towns found all across our state. Off the northwest coast in the Gulf of Mexico, Cedar Key is certainly a contender. This hidden gem is located a little off the beaten path, making it one of the best-kept secrets in the state. Cedar Key’s delightfully tiny downtown district is lined with charming shops surrounded by century-old oaks, perfect for a leisurely afternoon stroll. The area is best known for the Cedar Key National Wildlife Refuge comprising a group of small islands that feature stunning nature trails and excellent native wildlife viewing.

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Featured Addresses
Micanopy, FL, USA
Jacksonville, FL, USA
Apalachicola, FL 32320, USA
Quincy, FL, USA
Key West, FL 33040, USA
Tallahassee, FL, USA
Marianna, FL, USA
Fernandina Beach, FL 32034, USA
Pensacola, FL, USA
St. Augustine, FL, USA