7 of the Oldest Incorporated Towns in Florida

Florida is one of the nation's oldest regions settled by Europeans, with Spanish explorers, led by Juan Ponce de León, claiming the territory as early as 1513. It also has a multifaced heritage, with elements of Native American, Spanish, and English still visible in the small towns that dot the landscape. St. Augustine, the nation's oldest city, is a living history museum that transports visitors back to the First Spanish Colonial Period (1565-1764) with its vintage buildings, roads, and other heritage sites.

The state is rich in Native American heritage, evident in the memorials and street names of Micanopy and other small places. Each cultural legacy has shaped the region into what it is today: a cultural mecca that weaves the past and present into a unique tapestry. Here are seven of the oldest incorporated towns in Florida.

St. Augustine

The oldest European colony in the US, St Augustine, was founded by Juan Ponce de León in 1565. The small town remains virtually untouched, except for preservation efforts in the historic district, anchored by the pedestrian-only St. George Street, now lined with shops and landmark eateries like the Columbia Restaurant. The small roads, including Cuna Street, reflect the age of these ancient roads, culminating in the Castillo de San Marcos National Monument.

The fortification is St. Augustine's signature, which was built from 1672 to 1695 to protect Spanish claims in the New World. The small city swells with over 2 million annual visitors to see the fort, attend live reenactments, and visit other historic landmarks, such as the Oldest Wooden School House on St. George Street. The school was the Minorcan homestead of Juan Genopoly in the 1700s and today aims to interpret this vital heritage to the region.

Micanopy

Micanopy is the oldest inland city in Florida, settled in 1821, and one of the smallest at about 1.1 square miles. It is lovingly called "the little town that time forgot," and its abundance of antique stores at the Antique City Mall on Cholokka Boulevard is a primary reason so many visit this "old Florida" town. Spanish moss overhangs the boulevard lined with vintage brick storefronts and historic inns like Herlong Inn, built in 1845.

The Timucuan tribe inherited the small area near Tuscawilla Lake and the National Natural Landmark Paynes Prairie Preserve as early as 1539. Its name is derived from Chief Micanopy, a significant hereditary leader of the Seminole Nation during the early 19th century. Its first official American settlement was in 1823, two years after Florida became a US territory.

Mount Dora

Local lore suggests that Lake Dora, which Mount Dora is named after, is named after Dora Ann Drawdy (1819-1885), but this has yet to be proven. The area was first settled in 1874 by David Simpson and officially founded in subsequent years, including the addition of a Post Office in 1880. The town's official name was adopted in 1883 to reflect the fact that the settlement rests on a plateau 184 feet above sea level, a rare feat in Florida.

Grantham Park and the Mount Dora Lighthouse are prominent landmarks. The navigational aid is Florida's only freshwater lighthouse, guiding mariners on the large lake. The historic district offers a lovely tour of Florida history, enhanced by inns like The Alexander House and Lakeside Inn. The inn is the oldest continuously operated hotel in Florida, adding to Mount Dora's prestige and significance.

Fernandina Beach

Fernandina Beach traces its lineage to 1812 when Spanish Governor Enrique White established the town of Fernandina on Amelia Island, named for King Ferdinand VII. The Victorian center of the city revolves around Centre Street, home to the Florida House Inn and other legendary bed-and-breakfasts. It is also home to the Palace Saloon, Florida's oldest tavern, which opened in 1903.

Amelia Island has been settled since at least 1,000 A.D. by the Timucuan and other mound-building cultures, and much of this history has been preserved. Fernandina's recorded history has unfurled under eight flags, including French and Spanish, earning it the nickname "Isle of Eight Flags," evident in its different architectural designs and historic monuments, including the Fernandina Plaza Historic State Park.

Quincy

The inland town of Quincy was founded in 1825 and incorporated in 1828, named after President John Quincy Adams. It soon became an agricultural hub, known for its tobacco and cotton crops and later, its Coca-Cola investments. The crops and the investments made Quincy a historically prosperous town in Florida, known as "Coca-Cola Town," which, in 1907, was listed in several newspapers as the wealthiest city per capita in the US.

Many landmarks on the National Register of Historic Places, including the E.B. Shelfer House, the John Lee McFarlin House, the Quincy Library, and Soldiers Cemetery. The small town has a pivotal Civil War history, when the Gadsden Dragoons were formed to combat the Confederate Army, commemorated at the Gadsden County Civil War Monument and other historical markers. The Old Philadelphia Presbyterian Church, built in 1828, is another preserved slice of history honoring the town's founding less than a decade after the state.

Marianna

Marianna was founded by Scottish entrepreneur Scott Beveridge in 1828 and became the county seat of Jackson County the following year. He named it after his daughters, Mary and Anna, and the town drew the attention of farmers and plantation owners, offering an accessible river crossing on Christoff's Ferry. It is also known for the Battle of Marianna on September 27, 1864, during the Civil War, commemorated by the historical marker of the same name.

The Abstract Building is the oldest structure in town, built in the 1840s, and once housed the Central Office for the telephone exchange, established in 1801. The Davis-West House is another landmark, built by John Davis in the 1840s for one of his daughters, who married Dr. Theophilus West in 1859. Touring these sites and others provides a peek behind the curtain in one of Florida's most historic towns.

Key West

The little island of Key West has a fabled Native American history, dating to at least 800 A.D. It was home to the Calusa, Tequesta, and other peoples and was named Cayo Hueso in 1513 by Spanish explorer Juan Ponce de León. Its modern settlement started in 1821 when John Simonton purchased the island from Spain, and it was incorporated in 1828.

The island's natural deep-sea port attracted fishermen and sailors, and it grew into Florida's most populous city, finding financial prosperity in the 1850s through shipwreck salvage operations. Tangible interpretations of the small town's heritage are the Captain George Carey House, the Key West Women's Club, and the aptly named The Oldest House. The latter residence was built as the town incorporated and moved to its current location on Whitehead Street in 1829.

Florida is studded with old towns that are still shaped by their cultural heritage, from buildings to historic sites. They are among the best destinations for history and unique finds, such as the Castillo de San Marco in St. Augustine. Others, like Micanopy, are classic Florida towns with tree-lined streets and a sense of yesteryear.

Fernandina Beach and Key West have a lively character drenched in historical significance. While Fernandina's main drag, Centre Street, is lined with Victorian architecture, Key West has a laid-back island vibe and a commercial fishing heritage that add a unique flavor to its walkable streets. These are the oldest incorporated towns in Florida, and the best to visit for an authentic "old Florida" getaway.