10 Underrated Florida Towns Worth the Drive in 2026
The Apalachicola River takes its name at Chattahoochee. Near Fort Pierce, the lifeboat from the 2009 rescue of Captain Richard Phillips still shows the holes from SEAL bullets. In LaBelle, 17 painted bees on a honey company wall launched an art project with a goal of 50,000. Draws like those make these 10 underrated Florida towns worth the drive. A manatee spring, a strawberry harvest, and a cattle drive down a public street all make the cut. The route runs north to south and finishes on the Caloosahatchee River.
Chattahoochee, Florida
No river called the Apalachicola crosses into Florida from Georgia. The Chattahoochee and Flint rivers join in Lake Seminole, pass through Jim Woodruff Lock and Dam, and leave as the Apalachicola River. Chattahoochee, a Gadsden County town, watches that new river take shape.
Chattahoochee River Landing Park keeps the largest of seven mounds that once rose on the riverbank, according to the park's own markers. Building there got underway nearly 2,000 years ago in the Swift Creek era, and Mississippian peoples added to it centuries later. Two of the other six mounds are still visible. Workers rebuilt a smaller one to show the original shape, and the wrecks of several old river steamboats remain visible nearby.
Next door, Angus K. Gholson Jr. Nature Park shares 126 acres with the landing park, and 84 of those acres hold old-growth forest more than a century old. Its ravines shelter woods more reminiscent of Appalachian forest than typical northern Florida pinelands, with more than 400 plant species recorded. Spring brings trilliums, Florida flame azalea, and dimpled trout lily into bloom.
Live Oak, Florida
Since 1978, the Spirit of the Suwannee Music Park has staged concerts on more than 500 acres just north of Live Oak. The grounds reach the tea-colored Suwannee River, with a riverfront beach, canoe and kayak rentals, and a boat ramp. Concerts move between a music hall and an amphitheater.
Live Oak has served as the Suwannee County seat since 1868, and the river bounds the county on the north and west, with the Santa Fe River along its southern edge. The Suwannee County Courthouse went up between 1899 and 1904. It wears yellow brick, white cast-stone trim, and a clock tower under a copper dome.
On the same avenue, the Suwannee County Historical Museum opens on Fridays and Saturdays inside the old Atlantic Coast Line freight station. The depot recalls the early 1900s, when Live Oak ranked among the most important lumber and turpentine shipping centers in Florida. Florida Memorial University also traces its roots here, to a school Black Baptists founded in Live Oak in 1879.
Downtown hosts Christmas on the Square every holiday season, an outdoor market in the style of a European Christmas market.
Orange City, Florida
Nine hundred thirty-two manatees crowded into Blue Spring State Park on a single morning in January 2024. Researchers tracked 14 there in 1970. The park lies just west of Orange City in Volusia County, and its first-magnitude spring is the largest on the St. Johns River.
Inside the park, the three-story Thursby House dates to 1872 and rises from a shell midden. Louis Thursby, a Gold Rush prospector turned orange grower, built a pier there for passing steamboats.
Orange City took its name from the groves planted around it and incorporated on August 26, 1882. The city says its water won a silver medal at the 1904 St. Louis Exposition. Albert Dickinson gave the town the Dickinson Memorial Library in memory of his sister. The library's dedication came on December 17, 1919.
Back at the spring, the water holds 72 degrees all year. Manatees winter there from mid-November through March, and swimmers and tubers get the spring run from April 1 to November 14. Day visitors have needed a reservation since July 15, 2026.
Eatonville, Florida
Almost five years after Orange City incorporated, 27 electors gathered at Eatonville's town hall on August 15, 1887, and cast their votes. The Orange County town ranks among the oldest Black-incorporated municipalities in the United States.
Eatonville's most famous resident, Zora Neale Hurston, depicted the town in her 1937 novel Their Eyes Were Watching God. The Zora Neale Hurston National Museum of Fine Arts on East Kennedy Boulevard has shown work by artists of African descent since 1990. Its doors open on weekdays and Saturdays.
The Eatonville Historic District counts 51 contributing buildings from about 1882 to about 1946. Among them is the original building of St. Lawrence African Methodist Episcopal Church, now a residence on Kennedy Boulevard.
Each winter, the ZORA! Festival brings arts, education, and family days to town. The 2026 edition ran from January 30 to February 1, and more than 80 vendors set up for the weekend.
Maitland, Florida
Maitland wraps around Eatonville's northern and eastern edges. Its most unusual landmark opened in 1937 as an artist colony. The Maitland Art Center earned National Historic Landmark status in 2014 as a nationally significant example of Art Deco-Mayan Revival architecture. Twelve buildings share the grounds, and the galleries open Tuesday through Sunday.
The same museum group runs the Telephone Museum, where visitors can try a working switching station. It tells the story of the Winter Park Telephone Company, which Carl H. Galloway founded in Maitland.
Florida's Audubon movement also traces to this Orange County city. The Florida Audubon Society held its first meeting on March 2, 1900, at the lakeside Maitland home of Clara and Louis Dommerich. Today, the Audubon Center for Birds of Prey treats injured raptors on Lake Sybelia. The center first opened on October 19, 1979. In November 2025, it released its 800th rehabilitated bald eagle. The center reopened in February 2026 with a new owl aviary.
Clermont, Florida
A glass-enclosed deck 226 feet in the air tops the Florida Citrus Tower, which opened in Clermont on July 14, 1956. The city counts it among Florida's first attractions. Today an elevator climbs the equivalent of 22 stories to views that stretch 35 miles.
The Lake County city sits among the Clermont Chain of Lakes, part of the Palatlakaha River system, with its downtown on the Lake Minneola waterfront. Athletes arrive for the Orlando Health National Training Center, a warm-weather training base for hundreds of competitors, including high school, college, and professional athletes. Olympians and residents share Clermont's 10-mile Clay Loop and its rolling hills.
Back downtown, the Clermont Historic Village opens on weekend afternoons with free admission. Its Townsend House, built around 1895, was home to James and Sallie Townsend, the first African American couple to make their home in Clermont.
Plant City, Florida
Late winter belongs to the strawberry in Plant City, a Hillsborough County farm town. Growers plant more than 10,000 acres of berries each year in the greater Plant City area, about three-quarters of the nation's winter crop.
The Florida Strawberry Festival has celebrated that harvest since March 12, 1930, an idea from the newly organized Plant City Lions Club. It now runs 11 days. The 2027 edition is set for March 4 to 14.
In 2022, Florida made strawberry shortcake its official state dessert. The law notes that the festival serves about 200,000 shortcakes a year. It also recalls that Guinness World Records recognized Plant City in 2000 as home of the world's biggest shortcake at the time.
The 1909 Plant City Union Depot marks one of the few double diamonds in the Southeast, where two sets of railroad tracks cross a third. Nearby, the Downtown Plant City Commercial District fills the blocks between Baker Street, Wheeler Street, and the rail line. Inside the depot, the Robert W. Willaford Railroad Museum charges no admission and opens Tuesday through Saturday.
Fort Pierce, Florida
On North Hutchinson Island, the National Navy UDT-SEAL Museum honors the Navy's Underwater Demolition Teams and the SEALs who followed them. The Navy opened a combat demolition school at Fort Pierce on June 6, 1943, and the city is widely known as the birthplace of the Navy frogmen. A 2007 federal law recognized the museum as the official national museum of the Navy SEALs and their predecessors. The museum's collection includes the Maersk Alabama lifeboat, with the holes from SEAL bullets still visible.
In the city's Lincoln Park neighborhood, the Florida Highwaymen Museum opened in 2026 with one painting by each of the 26 Highwaymen in the Florida Artists Hall of Fame. These Black painters from Fort Pierce took up Florida landscapes in the late 1950s and sold their work from the trunks of their cars.
Downtown, the Sunrise Theatre opened on August 1, 1923. A restoration brought it back in 2006. Fort Pierce, the St. Lucie County seat on the Indian River, also maps the Zora Neale Hurston Dust Tracks Heritage Trail with eight markers. The Eatonville novelist lived here during the final years of her life.
Okeechobee, Florida
Cattle walk through Okeechobee on the fourth Saturday of July, during the town's Day of the Cowboy. Pioneers Peter and Louisiana Raulerson settled this part of what is now Okeechobee County in 1896, and the Florida East Coast Railway arrived in 1911.
Nearby, Lake Okeechobee covers 730 square miles yet averages only 9 feet deep. The South Florida Water Management District ranks it as the largest lake in the southeastern United States. The 143-mile Herbert Hoover Dike holds it back, and the US Army Corps of Engineers celebrated the substantial completion of its rehabilitation in January 2023.
The city calls itself the Speckled Perch Capital of the World. Its Speckled Perch Festival, the biggest of the year, lands in March.
On US Highway 98 North, the Okeechobee Livestock Market runs sales at noon every Monday and Tuesday. The market bills itself as the oldest family-owned and operated sale barn in South Florida, with a restaurant on site.
LaBelle, Florida
Seventeen painted bees launched Matthew Willey's The Good of the Hive, a project that aims to hand-paint 50,000 bees. They went up on a 125-foot wall at the Harold P. Curtis Honey Co. on North Bridge Street. Its shop sells palmetto, orange blossom, mangrove, and seagrape honeys. Willey has said LaBelle first told him murals were illegal, then changed the law two months later.
LaBelle, the Hendry County seat, grew from an 1880s settlement on the Caloosahatchee River. City literature dubs LaBelle the belle of the Caloosahatchee.
On the last full weekend of February, the Swamp Cabbage Festival fills Barron Park with a parade, a rodeo, and food vendors. Swamp cabbage is the edible heart of the sabal palm, Florida's state tree. The festival marked its 60th anniversary in 2026.
The Old Hendry County Courthouse dates to 1927 and keeps a 70-foot clock tower. Its National Register nomination calls it the region's most outstanding example of Mediterranean Revival architecture.
Where The Detour Pays Off
Timing shapes much of this route. Manatees crowd Blue Spring from mid-November through March, Plant City's festival claims late winter, and Okeechobee saves its cattle drive for July. LaBelle's swamp cabbage weekend lands in February, while Eatonville's festival straddles the end of January and the start of February. A river's first stretch, a lifeboat with bullet holes, and a wall of painted bees round out the reasons to leave the highway.
