27 Oldest Towns in Florida
The oldest towns in Florida may surprise you with their age and history. Florida is home to the oldest continuously-inhabited European settlement in the United States. Towns filled with history stretch across the state, from the very southern end to the western most points of the Panhandle.
Historic towns in Florida include many with ties to Native American tribes as well as the Spanish conquest of the state. Other old cities in Florida have surprising ties to many cities in New England. It seems Florida was a snowbird haven long before this century!
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I’ve always been interested in history. Twentieth century history doesn’t really make me giddy but start talking about things that happened 2,000 or 5,000 or 10,000 years ago, and I’m hooked on listening and learning.
Traveling to Ireland many years ago, I was struck by the amazing age and history of some of the buildings we ate and drank in.
We don’t have any buildings that old which are still in everyday use here in the US. In Florida, we definitely don’t, except maybe a couple of places in St. Augustine. Still, the history of Florida fascinates me as do the historic cities in Florida.
Here are the 27 oldest existing cities in Florida, by year of incorporation, not the year each was first settled as that’s just not reliably accurate in some cases.
NOTE: I get a lot messages that this list is inaccurate because someone’s family has lived in/farmed (insert town name) since 1800 (or whatever). I have no doubt that’s true. Many communities cropped up in Florida as homesteaders and pioneers banded together for security. However, the only way to accurately measure a town’s age for my purposes here was to use the first year of incorporation, when a town officially became a town. I hope you understand and appreciate the list even if your town isn’t on it.
1. St Augustine, 1822
The oldest continuously inhabited city of European origin in the United States, Pedro Menendez de Aviles founded St. Augustine in 1565. However, Ponce de Leon first explored the area around 1513, giving Florida the name “La Florida” for the many flowering plants he found. Huguenot, Rene Goulaine de Laudonniere, explored the area in 1564. He eventually established Fort Caroline further north near present-day Jacksonville. The Spanish, however, would prevail in establishing the first city of Florida.
History of St. Augustine
Named for Saint Augustine of Hippo, the patron saint of Menendez’s hometown of Aviles in Spain, St. Augustine was located near the Timucuan village of Seloy. Menendez quickly built a fort to protect his supplies and men. Remains of the fort have been found where the Fountain of Youth Archaeological Park is now located.
The first child of European descent was born here in 1566, 21 years before Roanoke and 42 years before the settlements of Santa Fe (NM) and Jamestown (VA). The first recorded birth of a black child came in 1606, 13 years before the first enslaved Africans arrived in Jamestown. What does this all mean? This old city in Florida deserves much more credit than it often gets.
Through the 1500s and 1600s, Native Americans, French, and British repeatedly attacked, raided, burned, and pillaged St. Augustine. Spain began construction of Castillo San Marcos in 1672 to further fortify the city. In 1733 the Spanish government established Fort Mose two miles north; it became the first legally recognized community of free ex-slaves.
British and Spanish Control of St. Augustine
The British controlled St. Augustine from 1763 to 1783. Most of the Spaniards and freedmen fled to Cuba during this time period.
In 1777, indentured servants brought from Minorca to New Smyrna rebelled against the deplorable conditions at that settlement. The group of settlers walked the 70 miles north to St. Augustine. The town’s governor granted them refuge. The Minorcans stayed in St. Augustine, their culture and customs influencing St. Augustine’s through the coming years.
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St. Augustine and Castillo San Marcos fell into disrepair during Spain’s second occupation from 1783 to 1821, in part because Spain’s resources were spread thin by conflicts in its other territories.
After Spain ceded Florida to the United States, Castillo San Marcos, then called Fort Marion, became a prison, first for Seminole Indians during the Seminole Wars, then as a prison for Plains Indians, and last as a prison during the Spanish-American War.
After 205 years in service, Castillo San Marcos was removed from operation and became a national park.
The Civil War and Civil Rights
Meanwhile, freedmen established the community of Lincolnville after the Civil War. Lincolnville had the most Victorian era houses in St. Augustine. The community held a pivotal role in the Civil Rights Movement. Thousands of black and white protesters picketed, staged sit-ins, carried out marches, and were jailed.
Between the Civil War and the Civil Rights Movement, St. Augustine became a winter retreat for wealthy northerners. Henry Flagler, railroad magnate, bought local railroads, built extravagant hotels, constructed churches, commissioned a baseball park, and built the first hospital in St. Augustine.
Some of the first theme parks in Florida could be found near St. Augustine, such as the St. Augustine Alligator Farm which opened in 1893 and the Fountain of Youth Archaeological Park, opened in 1902.
To this day, St. Augustine usually finds a spot on many people’s travel bucket lists, for it’s incredible history and architecture, as well as it’s wonderful food and seaside location.
2. Pensacola, 1822
By year of incorporation, Pensacola is the same age as St. Augustine. While St. Augustine is often called “the oldest continuously inhabited European settlement in the US,” Pensacola was actually the first multi-year European settlement in the continental United States making it Europe’s oldest settlement in Florida. That settlement, established in 1559, was abandoned two years later in 1561, four years before St. Augustine was settled.
The area where Pensacola now sits was not inhabited by indigenous people. The area did, however, provide hunting and fishing grounds to native tribes. The closest native settlement was located about 40 miles east of Pensacola. The tribes in this area and up to their ceremonial center near Mobile, Alabama lived near waterways and traveled mainly by dugout canoe.
Oldest Town in Florida
Exploration of the panhandle may have begun as early as 1516 with Diego Miruelo sailing into Pensacola Bay. The expeditions of Panfilo de Narvaez and Hernando de Soto passed through in 1528 and 1539, respectively.
In August 1559, Tristan de Luna y Arellano sailed into Pensacola Bay with 11 ships and 1500 people. About a month later, a hurricane decimated the new settlement. Six ships sank and supplies were ruined.
Many of the survivors moved inland into central Alabama for several months before returning to the coast. However, they abandoned the settlement after 2 years. Spain ignored the north Gulf Coast for approximately 140 years after that.
Pensacola’s Mixed Heritage
Beginning in 1698, Spain established three settlements in the Pensacola area. The first included a fort, village, and church. A hurricane destroyed it in 1722, then the French burned the rest of the village.
The second village was established on Santa Rosa Island in 1722. Hurricanes struck it in 1741 and 1752. Settlers relocated to the mainland. The third settlement lasted only a couple of years near present-day historic downtown Pensacola.
These early settlements near Pensacola in 1698 and another nearby in Wakulla county in 1733 served as garrison towns along the border with French territory in present-day Alabama. A Creole culture blossomed in Pensacola; marriages between Spanish soldiers and Pensacola Indians or African slaves were common, resulting in many mixed race descendants.
Known by several names early on, Spanish Royal order decreed the name Panzacola in 1757 for the village. It was not a popular place nor a popular military posting. Panzacola’s poor soil was not suited to agriculture, and it experienced irregular supply runs.
Pensacola has flown five different national flags – Spain (1559-1719, 1722-1763, and 1781-1819), France (1719-1722), Great Britain (1763-1781), United States (1821-1860 and 1862-present), and Confederate States of America (1861-1862). Florida Territory’s first capital was Pensacola, and territorial governor Andrew Jackson lived here until Tallahassee was named the new territorial capital.
Today, Pensacola is a popular vacation destination, offering beautiful Gulf Coast beaches, deep history, and award-winning restaurants.
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3. Tallahassee, 1824
Native Americans have lived in the hills around Tallahassee for 10,000 years. Close to 30,000 people lived in the village where Florida’s capital now stands. The Apalachee, one of the tribes which lived here, traded pottery as far north as the Great Lakes. They also constructed temple mounds, as did many of Florida’s other native tribes.
By the 1700s, most of the indigenous tribes had been wiped out by disease or warfare. The word “tallahassee” came from a Muskogean word meaning “old field” or “old town”.
How Tallahassee Became State Capital
When Florida became a US territory in 1821, the legislature chose a place midway between St. Augustine and Pensacola, the two oldest Florida towns, for the territory’s capital. The location was determined by sending a rider West from St. Augustine and a rider East from Pensacola. Both riders traveled on the Old Spanish Trail, a road created by the Spanish between the two towns. They met at or near the old Indian village and placed the capital there.
The Lafayette Land Grants of 1825 brought large land owners such as General Marquis de Lafayette and Prince Achille Murat, Napoleon Bonaparte’s nephew. Many of these early plantations failed and the workers left for New Orleans. Others stayed behind, creating an area still known as Frenchtown.
Early Tallahassee was a rather lawless place. Ralph Waldo Emerson described Tallahasse as “a grotesque place of land speculations and desperados.” By 1837, however, the Tallahassee Police Department and a growing plantation economy helped the town grow.
The Civil War and Beyond
During the Civil War, Tallahassee was the only state capital east of the Mississippi not captured by Union forces and the only one not burned. One battle occurred outside of Tallahassee, the Battle of Natural Bridge, which was fought by students of what would become Florida State University.
The railroad arrived in the 1880s. Banks grew as did a state university. With all of the growth, Tallahassee settled into a quiet town and grew as well.
4. Fernandina Beach, 1825
Located in Florida’s most northeastern corner, Fernandina Beach lies on Amelia Island where the native Timacuan village, Napoyca, once stood. Fernandina’s history is deeply tied to Amelia Island history.
Amelia Island is the only part of the United States which has flown eight different national flags, giving it the moniker “Isle of 8 Flags.” Those eight nations were: France, Spain, Great Britain, Republic of East Florida, Republic of the Floridas, Mexico, United States, and the Confederate States of America.
Isle of 8 Flags
Up until 1847, Amelia Island passed through numerous hands. The Spanish and French seized control of the island at the same times as they did Jacksonville. The British controlled all of Florida for 20 years prior to Spain regaining control in 1783.
Fernandina was platted and named in 1811 by Enrique White, governor of East Florida. In 1816, Spain built Fort San Carlos on Amelia Island. Scottish Soldier, Gregor McGregor, took control of the fort and claimed Amelia Island for “the brethren of Mexico, Buenos Ayres, New Grenada and Venezuela.”
The US Army began construction on Fort Clinch in 1847. The railroad reached Amelia Island In 1855, and the town of Fernandina moved one mile south, closer to the railroad depot.
Confederate forces seized Fort Clinch in 1861. The fort was retaken in 1863 by a Union regiment comprised entirely of former slaves.
After the Civil War, Fernandina Beach saw slow growth and is still a small town today with a focus on tourism.
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5. Apalachicola, 1827
Apalachicola sits on Florida’s Big Bend, the place on the upper Gulf Coast where Florida’s peninsula bends into the rest of the country. It’s a small town at the mouth of the Apalachicola River which flows into Apalachicola Bay and is best known for its fresh seafood, especially oysters.
The word Apalachicola likely comes from several Hitchiti words meaning “people from the other side of the river”. It first referred to the native people who inhabited the area and later became the name of the river, the bay, and the town.
Some in Apalachicola say the name means “land of friendly people”. The town strives to maintain its old Florida charm and southern hospitality with quaint shops, cozy B&Bs, and award-winning restaurants.
History of Apalachicola
Though the area around Apalachicola was inhabited by native Americans for hundreds of years, white settlers didn’t move into the area until the British established a trading post here sometime between 1763 and 1783. Named “Cottonton”, it remained in operation by the Spanish when they reacquired Florida in 1783.
After the US gained control of Florida in 1821, white settlers trickled into the area. The town of West Point was incorporated in 1827 at the site of the former Cottonton. In 1831, the town name changed to Apalachicola.
By 1837, Apalachicola boasted 2,000 feet of waterfront on the river which included three-story brick stores and buildings. Until the railroad reached the town in the late 19th century, Apalachicola was the third busiest port in the Gulf of Mexico behind New Orleans and Mobile.
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Apalachicola Firsts
While Florida’s population exploded the last few years, Apalachicola’s only increased by 55 people between 2010 and 2021. Known for its laidback vibe, oysters, and riverfront, it’s not the kind of town one imagines to be at the forefront of engineering miracles. And yet, it is.
In 1837, Christ Church (now Trinity Episcopal Church) was one of the first prefabricated buildings in the United States. The framework, constructed in New York, arrived by schooner and was put together on-site with wooden pegs.
Twelve years later, in 1849, Dr. John Gorrie created the first ice machine using refrigeration principles he discovered in an attempt to keep his Yellow Fever patients comfortable. These principles form the basis for the air conditioning we use today.
Apalachicola Today
Today, Apalachicola hosts the Florida Seafood Festival. It’s also a quiet place where couples and families spend a night or two to enjoy fresh local seafood. Unfortunately, the oyster industry has been in decline the last few years due to water pollution and a lack of flow from the Apalachicola River.
Apalachicola is the only place in the United States where, by law, oysters can only be harvested with tongs using small boats. This law shows Apalachicola’s commitment to preserving its history and conserving its natural resources. As of 2024, however, oyster harvesting is temporarily suspended.
6. Key West, 1828
Key West, an anglicization of Cayo Hueso, lies 150 miles from mainland Florida and only 90 miles from Cuba. The island was first discovered in 1521 by Ponce de Leon who gave it the name Cayo Hueso (“Bone Island”) because of the bleached limestone found around the island.
By Ebyabe – Own work, CC BY-SA 3.0
One of the Most Historic Towns in Florida
Shallow reefs surround Key West, and these gave rise to the island’s main industries in the 1800’s – wrecking, salvage, turtling, and salt manufacturing. Key West was the richest city in the United States from the 1830s through the 1850s.
DID YOU KINOW? Tennessee Williams wrote the final draft of “A Streetcar Named Desire” in Key West. –Key West Art and Historical Society
During the Civil War, Key West remained part of the Union, thanks in part to Fort Taylor, a naval fort. During this time, Key West also saw an influx of Cuban refugees fleeing the Ten Years War in Cuba. Many of them, or their descendants, established businesses on Key West which still exist today.
Since the early 1900s, Key West has become a tourist industry driven town. The Henry Flagler railroad connected the island with mainland Florida. With easier access more tourists visited the island. For instance, famous writers Ernest Hemingway and Tennessee Williams wrote some of their works while living in Key West.
7. Marianna, 1828
Marianna has a troubled past, as do many Southern towns. Located in Florida’s panhandle, Marianna lies along the Chipola River, platted by Scotsman, Scott Beverage. He named the town after his two daughters, Mary and Anna. In 1829, Marianna was named county seat of Jackson County after a bitter feud with nearby Webbville. The latter town soon ceased to exist.
The Civil War brought a couple of battles to Jackson County. After the war, secessionist and Florida Governor, John Milton, committed suicide at his plantation in Marianna when he learned the war ended, and Florida would rejoin the union.
By Ebyabe – Own work, CC BY 2.5
Through Reconstruction and into the 20th century, tensions remained high between white citizens and African American citizens. Many lynchings occurred in the small town, and Florida actually led the country in lynchings in the 20th century.
The Florida School of Boys also operated in Marianna from 1900 to 2011. Rumors stated many boys died in the juvenile detention facility. The school also gained a reputation for abuse, rape, and torture of the boys by staff members.
Marianna today attracts visitors to Florida Caverns State Park. The Federal Correctional Institute, Marianna, a medium security US federal prison, is also located there.
8. Quincy, 1828
Quincy, in North Florida near the Panhandle, lies just 25 miles from Florida’s capital, Tallahassee. The town is the county seat of Gadsden County and has a history in agriculture. Early crops included tomatoes, tobacco, corn, soybeans, and mushrooms.
By Ebyabe – Own work, CC BY-SA 3.0
From 1828 to the 1970s, tobacco was Quincy’s cash crop. Virginian John Smith moved his family to the area in 1827-1828 and brought his Virginia tobacco.
Meanwhile, Florida territory Governor, William Duval, imported Cuban tobacco. The resulting hybrid brought land investors from New York who financed tobacco farms.
The tobacco industry remained strong until the decline of smoking starting in the 1970s. Now, the tobacco industry in Quincy no longer exists.
Quincy has two other claims to fame. The town’s first newspaper, the Quincy Sentinel, moved to Tallahassee in 1841 and became the Florida Sentinel, one of Florida’s largest and oldest newspapers. Also in the 1840s, Quincy founded the first public schools in Florida – the Quincy Male Academy and the Quincy Female Academy.
9. Jacksonville, 1832
Jacksonville shares a long and somewhat troubled history with St. Augustine 65 miles south. The Mocama, a coastal subgroup of the Timuqua, originally inhabited the region. Archaeological evidence shows people lived here as early as 6500 years ago. Archaeologists recovered pottery dating to 2500 BC, some of the oldest pottery found in the United States.
Early Europeans in Jacksonville
European settlement first came to Northeast Florida when Rene Goulaine de Laudonniere founded a colony on the St. Johns River and constructed Fort Caroline in 1564.
Meanwhile, the Spanish had founded St Augustine, and each intended to oust the other from Florida. Pedro Menendez de Aviles of Spain would be victorious.
During one planned raid, bad weather stranded 600 soldiers & sailors from Fort Caroline at sea on their way to St. Augustine. Menendez de Aviles burned down Fort Caroline in their absence and spared the lives of only 50 women and children.
His sailors then hunted down the French troops at sea and killed all but 20 of them. The Spanish abandoned Fort Caroline in 1569 and nearby Fort Saint Nicholas in the 17th century.
Photo credit Florida Memory
In 1763, Florida came under British rule, and England gave land grants to their soldiers, extolling Florida’s natural virtues to encourage settlement. The Jacksonville area prospered. King’s Road connected St Augustine to Georgia and passed through the Jacksonville area.
The British introduced new crops, such as indigo and various fruits, built public roads, and introduced the British court system. After Florida reverted to Spain’s control in 1783, settlers continued to cross the border from the newly formed United States.
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Jacksonville as Part of the US
Jacksonville acquired its name in 1822 in honor of Andrew Jackson. The city became a major supply port during the Civil War and was occupied by both sides several times. The Reconstruction Period saw Jacksonville prosper as a winter retreat for wealthy Northerners. Jacksonville continued to grow and prosper through the 19th and 20th centuries.
The city is now the largest, by area, in the United States, and one of Florida’s major cities.
10. Micanopy, 1837
Micanopy was the first interior town to be settled in Florida. First inhabited by the Timucua and Seminole, a small group of white people settled on the site as early as 1817. The town acquired its name from the Seminole chief, Micanopy. Lore holds that officials chose this name to honor Chief Micanopy’s original authority in the area.
Two battles of the Second Seminole War destroyed much of the original town. Fort Defiance first stood at Micanopy during 1835-1836. Seminoles burned it to the ground. Fort Micanopy replaced Fort Defiance in 1837.
DID YOU KNOW? Micanopy has been used as the setting in two movies – Cross Creek (1983) and Doc Hollywood (1991).
Micanopy is also the site of the first Jewish communitarian settlement in the US. Moses Levy established Pilgrimage Plantation in 1821 and brought 48 Jewish families from Europe to avoid persecution on that continent. The Seminoles burned down the plantation during one of the Seminole Wars. Levy’s legacy lives on, however, in his son, David Levy Yulee, who was the United States’ first Jewish senator, and in the small Jewish Community still alive in Micanopy.
11. Milton, 1844
Milton is a small town on Florida’s panhandle which has had many names. It was first settled in the early 1800s with industry centered around lumber and timber. Locals called the town Hell Town, Jernigan’s Landing, Scratch Ankle, and Hard Scrabble. Eventually it became known as Milltown, later shortened to Milton.
Located near Pensacola, Millton suffered the wrath of the Confederate Army during the Civil War. When Pensacola was captured by the Union in 1862, the Confederates burned down most of Milton as they retreated the area, an attempt to prevent the town’s industries from falling into Union hands.
Milton was rebuilt and now hosts a Naval Air Station Whiting Field. It’s also the site of one of Florida’s deadliest tornados, an F-3 which touched down in 1962. Perhaps more surprising, Milton has produced nine professional athletes, including five NFL players, and Dan Amos, the cofounder of Aflac, is from Milton.
12. Tampa, 1849
Native Americans lived in the Tampa Bay area as early as 500 BC. Several independent chiefdoms called this region home including:
- Tocobaga, whose principal village was located in present-day Safety Harbor where Philippe Park now sits.
- Uzita along the south shore of Tampa Bay in present-day Manatee County and south to Sarasota.
- Mocoso on the east side of Tampa Bay along the Alafia River and possibly to the Hillsborough River.
- Pohoy or Capaloey near present-day downtown Tampa and possibly into the Hillsborough River.
The Tampa Bay Area was first explored by Panfilo de Narvaez in 1528. Spanish settlements by both the Narvaez expedition and de Soto’s expedition quickly ceased to exist in the Tampa Bay area as the indigenous people waged war on them.
During the 18th century, after native populations were decimated by disease, seasonal residents used Tampa Bay. Cuban fisherman caught and smoked mullet and other fish in the bay then returned to Cuba to sell their catches.
After the war of 1812, a community of escaped slaves established a community on the south shore of Tampa Bay near present-day Bradenton. Angola, as they called the community, existed until 1821 when the United States acquired Florida. Territorial Governor, Andrew Jackson, ordered the community destroyed. Those who survived Angola’s destruction fled to the Bahamas.
DID YOU KNOW? In the early 1900s, Tampa city officials created a fake story about the “pirate Jose Gaspar”. A pirate ship sailed into Tampa Bay and pretended to take over the city. So began Tampa’s most popular annual festival, Gasparilla.
Tampa’s Difficult Early Years
Fort Brooke, built in 1824, helped enforce the Treaty of Moultrie of 1823. The fort was located roughly where the Convention Center now sits. A small village slowly grew around the fort. The Hurricane of 1848 destroyed or damaged much of the fort and town, but the residents stayed and rebuilt the town.
Tampa’s population was decimated during the Civil War. By 1867, however, the town had rebuilt and shipped cattle, oranges, and other produce from its small port to Cuba, Key West, and New Orleans. However, several yellow fever epidemics in the 1860s deteriorated city conditions, and it was unincorporated in 1869. Reincorporated in 1872, Tampa grew quickly after the railroad reached the town in the early 1880s.
13. Archer, 1850
Archer, located north of Gainesville, has a rather quiet history. First settled in the 1840s, the town was called Deer Hammock and then Darden’s Hammock before being incorporated as Archer in honor of Florida’s first Secretary of State, James Archer.
The town grew up around the railroad depot and had several prosperous businesses including a sawmill, hotels, saloons, and nine general stores. Rumor says that a cache of Confederate gold is buried somewhere in or near Archer.
14. Palatka, 1853
Palatka is located on the banks of the historic St. Johns River. This part of the river is the southernmost point where ocean-going vessels can pass. South of this point, only river boats can navigate the St Johns. This led to Palatka’s importance and the town being known as the “Gateway to the Interior of Florida.”
By Ebyabe – Own work, CC BY 2.5
Cattle ranching was the main use of the land here in the 17th century. By the 18th century, the cattle ranches were abandoned, and a Seminole village existed along the St Johns. The town’s name came from the Timucua word “pilotakata” meaning “crossing” or perhaps the Seminole word “pilatka” meaning “cow crossing.”
Fort Shannon was established on the site in the early 1800s and served as a supply depot and hospital for nearby forts. After the Civil War, Palatka was a thriving river port and winter retreat. The city became known as “Gem of the St Johns.”
15. Jasper, 1858
Jasper is a small town in north Florida, about 32 miles north of Lake City. Little is known about the town’s history; several courthouse fires destroyed records.
Local legend says the town is built near or on a Miccosukee village. Some say Chief Billy Bowlegs lived at the nearby village of Halata-Micco and that an Indian mound is located in Baisden Swamp.
This village was known as Micco, and Jasper may originally have been called Miccotown, meaning “next house over from the Chief’s” which would have been Daniel Bell’s nearby homestead as he was the only settler there.
Another name used later was Wallburg, for Peter Wall who first settled in present-day Jasper before moving to Tampa.
By Ebyabe – Own work, CC BY 2.5
Jasper was named for Revolutionary War hero, Sergeant William Jasper. The railroad came to within a mile of Jasper’s original location. Businesses eventually moved closer to the railroad depot effectively moving Jasper to its present location.
16. Lake City, 1859
Lake City is located 60 miles west of Jacksonville at the crossroads of I-75 and I-10. As such, it’s known as the “Gateway to Florida.”
Early occupation in the area appears to be Spanish missions. A branch of the western Timucua called the northern Utina may have lived in this part of Florida as well.
By the 18th century, there was an established Seminole village near present-day Lake City. The village was called Alpata Telophka (Alligator Village) and gave Lake City its first name.
By Ebyabe – Own work, CC BY 2.5
When white settlers established a village near Alpata Telophka in the early 1800s, they named it Alligator. Two forts were built during the Seminole Indian Wars – nearby Fort White along the Santa Fe River and Fort Lancaster where downtown Lake City now stands.
Alligator grew, thanks to railroad service.
In 1859, the town name was changed to Lake City. Some say it was because the mayor’s wife refused to hang her curtains in a place called Alligator. Others say a local woman’s daughter who was away at college was embarrassed to tell others her family lived in a town named Alligator. The mother petitioned for a name change which was granted by state senators.
17. Monticello, 1859
County seat of Jefferson County, Monticello is nonetheless a small town of less than five thousand people in Florida’s Big Bend region. It is also the only incorporated town in Jefferson County. The Aucilla River Prehistory Project (ARPP) has dated human habitation along the Aucilla River in Jefferson County to more than 10,000 years ago.
Europeans first traveled through the area in 1528 when Panfilo de Narvaez’s expedition passed through an Apalachee village. Five Franciscan missions were organized here in the 17th century but were destroyed by the English governor of the Carolinas in the 18th century. Miccosukee, a branch of the Creeks who later became Seminoles, occupied the region after that.
By Ebyabe – Own work, CC BY 2.5
American settlers bought land around Monticello in the early 1800s for timber and cotton production. Robinson’s Post Office became the county seat of Jefferson County and was renamed Monticello shortly after.
The town suffered many losses, first when many of its citizens left to fight in the Seminole Wars, and then with failure of the Union bank. The town’s bad luck continued when the railroad bypassed Monticello for Aucilla 3 miles south, and finally crushed by debt incurred after the Civil War.
18. Port Orange, 1867
Located just south of Daytona Beach on Florida’s Atlantic Coast, Port Orange has its origins in the lives of a plantation and those of freed slaves.
The first settler to this area was Patrick Dean who received a land grant from Spain in 1804. He established the Dunlawton Plantation on the 995 acres.
Sarah Anderson bought the plantation in 1832 after Dean’s death and named the growing settlement around it Dunlawton. However, the plantation was burned to the ground twice in Seminole raids during the Second Seminole Indian War.
The sugar mill survived and still stands though the area was largely abandoned until after the Civil War.
By Florida History Network
In 1866, Dr. Milton Hawks brought 500 freed slaves to what would become Port Orange to work at his lumber mill.
By 1869, the mill and settlement had failed, leaving only nine African American families. They unofficially called their settlement Freemanville.
It was officially annexed into Port Orange years later though the only thing that remains of the early settlements, besides the sugar mill, is the Mount Moriah Baptist Church.
19. Ocala, 1868
Ocale, or Ocali, was a major Timucua village near present-day Ocala. The name means ”big hammock’ in the Timucua language. Archaeological evidence shows the area was occupied from 6,500 BC to the mid-1500s.
The area seems to have been abandoned after de Soto’s raid in 1539. It was again settled sometime in the 1600s but was raided by Carolina soldiers and Yamassee Indians in 1715.
Non-native settlement began with land grants from Spain before Florida was ceded to the United States in 1821. The US Army constructed Fort King in 1827, and it became the county seat of Marion County in 1844. Shortly after, Ocala was platted west of Fort King, including a city square, courthouse, post office, and a newspaper.
An African American Oasis
Ocala’s economy in the 1850s and to the mid 1860s was one of antebellum plantations with corn, sugarcane, cotton, and tobacco as the main crops. African Americans made up the majority of the population until the land boom of the 1920s.
After the Emancipation Proclamation, many former slaves remained in Ocala and continued to work as paid workers on the plantations. They would shape the early history of Ocala. Many prosperous African Americans from Ocala served in state and local politics, started businesses, established schools and churches, and became professionals.
Ocala Star-Banner
Some of their accomplishments include:
- The Howard Academy opened in 1867 and was the school for many future professionals in the African American community.
- Appointment by the Republican party of Edward Barker to the office of Judge of Probate in 1869.
- M. A. Clout appointed sheriff in 1868.
- Seven African American representatives from Ocala were sent to the Florida house by 1879.
- There were 38 African American schools for 2,476 students by 1891.
- Incorporation of Metropolitan Savings Bank in 1914, Florida’s first African American Bank.
- Effie Carrie Mitchell became the first African American woman to practice medicine in Florida. She was married to Dr. Hampton, an African American physician, who studied at Howard Academy with her.
Most of Ocala burned in the Thanksgiving Day fire of 1883. The city was rebuilt with brick and metal and became known as “The Brick City.” Ocala weathered the land boom of the 1920s and the Great Depression in the 1930s.
DID YOU KNOW? Silver Springs, the largest freshwater spring in Florida, was the state’s first tourist attraction.
In the 1940s, as horse racing became popular, breeders discovered Ocala, and Marion County became known as a “Horse Capital of the World,” a name it still holds today.
20. Gainesville, 1869
Best known today for the University of Florida, Gainesville history stretches far beyond its year of incorporation. The city lies among numerous lakes and creeks including Paynes Prairie which becomes a lake in times of heavy rain.
Not surprising, numerous different tribes of indigenous people used this area for many thousands of years. We know the Deptford Culture (2500 – 100 BC) occupied the area and later became known as the Cades Pond culture in this area.
These people were displaced by the Alachua culture in the 7th century. Forest trails connected several Alachua villages in the area. These became the Patano, a Timucua chiefdom.
Spanish Occupation of Gainesville
In 1539, Hernando de Soto passed through the Gainesville area and stayed at the Village of Utinamocharra northwest of present-day Gainesville. European diseases wiped out much of the native population. Those who remained converted to Roman Catholicism, and three missions organized by Franciscan priests were established, starting in 1606.
By (WT-shared) Mistoffeles at wts wikivoyage
In the early 1700s, soldiers from the Province of Carolina, raided the area. They, with their Yamassee Indian allies, killed or enslaved most of the remaining native population. Those who escaped fled to St Augustine.
Around this time, Spanish colonists had also ranched cattle near Paynes Prairie south of present-day Gainesville. The largest hacienda was named La Chua (“sinkhole” in the local native language). The ranch was raided and destroyed by the Carolina soldiers but gave its name to a Seminole tribe which later settled here, as well as the present-day county and a nearby town.
Gainesville in the Florida Territory
Gainesville was built specifically as the Alachua County county seat along the route of the Florida Railroad from Fernandina Beach to Cedar Key. The town site was selected in 1854, the courthouse built in 1856, and the jail and public well built in 1857.
Gainesville may have experienced the first land boom in Florida. Land prices increased more than fivefold with a city block that sold for $14.57 in 1857 selling for $100 in 1858. The railroad reached Gainesville in 1859.
For two decades after the Civil War, Gainesville was both a diverse town and a rough town. Whites and blacks equaled in number in population and in elected office. The black public school, the Union Academy, was a better quality school then the white public school, because it was in session for a longer period of time and had more funding.
During this time, many citizens carried firearms and gunfire could be heard well into the night. Killings were not unusual. Gainesville grew nonetheless, and in 1906 the University of the State of Florida was established, paving the way for the college town we know today.
21. Starke, 1870
Not much is known about the Starke area prior to the railroad coming to town in 1858. Part of the reason is that early homesteaders, like Drury Reddish, disagreed with the construction of the railroad. There were also two courthouse fires in later years which destroyed many early records. We don’t even really know how the town got its name.
After the railroad’s arrival, a post office and general store were established. Then came the Civil War.
Largely untouched by fighting, Starke still saw some action. Captain Richard (pronounced Reshard), one of the earliest merchants in Starke, commanded a company of militia throughout the war.
Local folklore says he was injured in Virginia. Back home in Starke some months later, Union forces came looking for him. He escaped from his home, followed a nearby creek to the railroad trestle bridge, and hid there for several days.
Starke remained relatively quiet except for a political fight to become the county seat of Bradford County, which it eventually won. Today it is still a quiet town of less than 10,000.
22. Green Cove Springs, 1874
Years ago I took a drive to the Clay County Building Department in Green Cove Springs. I was wearing a pink pantsuit, and I remember everyone was so incredibly nice, unlike many other building departments I had had the misfortune of dealing with.
I stepped off the elevator to a wide, open room, and one woman behind the counter called out, “Pretty in pink!” She was such a sweet person to work with, the epitome of the friendliness found in Green Cove Springs.
History of Green Cove Springs
Green Cove Springs lies along the historic St. Johns River in Northeast Florida. As such, the area has always been a desirable location, with native people first using the site around 7,000 years ago.
In 1816, George Clarke gained a land grant from Spain and established a lumber mill. After Spain ceded Florida to the United States in 1821, the Green Cove Springs area became a popular winter retreat with northerners.
First named White Sulphur Springs, the mineral spring here is often called “the original Fountain of Youth” for its medicinal waters. The name Green Cove Springs refers to the evergreen quality of the foliage plus the bend in the St. Johns River which makes a natural safe harbor plus the spring.
By Ebyabe – Own work, CC BY-SA 3.0
Green Cove Springs Firsts and Famous Folks
Green Cove Springs led the state in many “firsts”including:
- The first trolley system in the state, used to transport tourists and goods from the riverboats to the hotels surrounding the spring.
- The first Ford dealership in the state, owned and operated by Mr. Gustafson, founder of Gustafson Dairy.
- The first Model T to be delivered in Florida was, unsurprisingly, delivered to Mr. Gustafson.
- The first Federated Women’s Club of Florida was established in Green Cove Springs.
The city is also associated with or home to many famous Americans, such as:
- Augustine Christine Fells Savage, an African American sculptor who worked during the Harlem Renaissance period. Green Cove Springs named the high school for her.
- Charles Merrill, son of Dr. Merrill who was a physician in Green Cove Springs in the 1880’s. Born here, Charles moved to New York, and co-founded Merrill Lynch.
- James Cash Penney, owner of J.C. Penney, developed Penney Retirement Community near Green Cove Springs.
- A.G. Shands built the Shands Bridge which spans 2.5 miles across the St. Johns River. It is the longest wooden bridge in Florida.
- Colonel Ed McMahon, the famous actor, served here in the military as a flight instructor during World War II.
23. Orlando, 1875
Best known today as the Theme Park Capital of the World, Orlando served an important function starting in the 1820s. The original settlement, named Jernigan, grew around Fort Gatlin just south of present-day Orlando. The US Army built the fort to protect settlers from Indian attacks during the Seminole Indian War. Sounds innocent enough, right? Well, that’s not all of the story.
While several different Native American tribes established villages throughout Florida, no evidence exists to show that any of them lived in the Orlando area. Despite this, the Treaty of Moultrie Creek established a Seminole reservation in 1823 in central Florida, including present-day Orlando.
Seven years later, the Indian Removal Act authorized the relocation of Seminoles to Oklahoma. The Seminoles disagreed with that authority. And so began the Second Seminole War, during which the US Army built Fort Gatlin.
By Florida Memory
After incorporation in 1875, the population of Orlando exploded. It became the epicenter of Florida’s citrus industry until the Great Freeze of 1894-1895 which annihilated the citrus groves. Orlando remained a small town until Walt Disney began buying up swamp land in the 1950s and 1960s. The rest is theme park history.
DID YOU KNOW? Walt Disney began buying land for Disney World in 1964, eventually purchasing 30,500 acres through several dummy corporations. –Frommer’s
24. Leesburg, 1875
Located north of Orlando in central Florida, the Robertson family first settled in the Leesburg area in 1842 or 1843. Eleven years later, the family moved back to Moss Bluff near present-day Ocala.
Evander Lee purchased the Robertson homestead in 1857 and moved his wife and eight children to it. However, it was Evander’s brother, Calvin, who first called the settlement “Leesburg”. When asked where to ship supplies on a trip to New York, Calvin replied, “Leesburg in Florida.”
By Ebyabe – Own work, CC BY-SA 3.0
Soon, other families joined the Lee brothers. Leesburg became known as a place with mild winters, miles of waterways and lakes (Leesburg is in Lake County) and beautiful countryside. Within 20 years of Evander’s arrival, Leesburg offered its residents several churches and schools, a newspaper, stores, government buildings, and even an opera house.
25. Longwood, 1875
Now a suburb in the Orlando Metro area, Longwood was first settled in 1873 when John Neill Searcy from Tennessee and Edward Warren Henck from Boston gained homesteads in the area. One other family, the Hartleys, were already there. Henck named the settlement Longwood after a Boston neighborhood he helped plat as a young engineer.
Longwood became something of an entry point for other Florida pioneers. For example, Peter Demens first lived in the Longwood area; St. Petersburg near Tampa was named for Demens’ hometown in Russia.
Other pioneers include well-known names, such as Henry Plant who purchased controlling interest of the South Florida Railroad from Henck. Plant went on to establish railroads and hotels throughout Florida’s Gulf Coast.
26. Daytona Beach, 1876
This one surprised me; we so often think of Daytona Beach as a party-going, Spring Break town. Did you know Daytona Beach is also where auto racing got its start?
By Ebyabe – Own work, CC BY-SA 3.0,
Back in 1870, Matthias Day purchased 3,200 acres for $1,200. Oh, to have a time machine and go back to purchase land at those prices! The town that grew there became known as Daytona Beach. Nearby towns Daytona and Seabreeze became part of Daytona Beach in the early 20th century.
DID YOU KNOW? NASCAR ran its first race on the beach road course at Daytona Beach in February 1948. –Nascar History
Known for its wide, packed-sand beach, Daytona Beach became a mecca for automobile testing and later for auto racing enthusiasts. By the mid-1920’s, Daytona Beach earned the moniker “World’s Most Famous Beach.”
27. Sanford, 1877
Pre-columbian habitation around Lake Monroe included the Myaca or Jororo Indians. Later, the Seminoles lived along the lake’s shores. The US Army established Cape Monroe, an army garrison, in response to the Seminole Wars then later fortified it and named it Fort Mellon.
Mellonville grew around the fort during the 1840s and 1850s. Sanford, however, became the town that survived, established west of Mellonville on 12,000 acres in 1870. Sanford annexed the older town six years later.
Sanford’s success came largely from the railroad and agriculture. By 1883, the town was the largest shipper of oranges in the world. After the great freeze of 1894 – 1895, farmers diversified their crops. Today, many call Sanford “Celery City”.
Closing: Oldest Cities in Florida
The oldest towns in Florida showcase Florida’s unique and amazing history. Home to some of the oldest settlements in the United States, these became the historic towns of Florida. Despite the oldest city in Florida dating back to the 1500s, the state remains young at heart, rarely flaunting it’s many achievements over the years.
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yeah where is cedar key, where is homosassa, where is the REAL old places not these places i am a 4th generation floridian and you didnt get this right at all
Thank you for your comment, Jamie. There are, indeed, many old and historic towns that are not on this list. I used the official incorporated date to compile this list. Unfortunately, though many towns in Florida were settled or the area inhabited long before a town was incorporated, to use a different method to compile this list would mean I would have to guess at which towns to add. Additionally, there are many towns which are far older but were abandoned or never incorporated. And to add to the confusion of which towns are the oldest, we have to consider all of the Native American villages which were wiped out by Europeans or bulldozed for the shell middens to be used for roads and other construction projects. I’m sure we can agree that those are truly the oldest towns in Florida.
Where is cedar key?
Florida has such a rich history! This is a great bucket list for travel.
That’s a great idea! It really is.
This is such a great guide, I had no idea old neighborhoods and areas like these existed in and aroudn Florida! definitely something I would have missed had I not stumbled upon this blog post!
This is cool, I have visited most of these cities. The mots beautiful is definitely St Augustine.
YESSSS! This is my kind of post about Florida. There are SO many cool historic places in this state and people miss. I only got to see a few of them, but I loved visiting, especially where the historic cobblestone streets are still around. Great guide.