9 Playfully Peculiar Towns In Florida
Florida is undoubtedly one of the world’s top destinations for tourists from all over the planet who travel great distances to spend time on the beaches and in the art deco historic district of Miami Beach, explore far away galaxies and the astronauts who mingle with the stars at the Kennedy Space Center, snap selfies with Mickey and Minnie at Walt Disney World, and hitch a swamp ride on an airboat through the Everglades. If waiting in long lines, pricey attraction tickets, and crowds aren’t your thing, here are nine playfully peculiar towns in Florida, with quirky landmarks, bizarre nicknames, and much to explore. Rich in personality, character, and spunk, these small towns are perfect for travelers who like charm, originality, and a dash of the unexpected.
Mount Dora
Mount Dora is a peaceful lakeside retreat about 35 minutes northwest of Orlando. Nicknamed “Festival City,” the town hosts over 25 festivals annually, including the Florida Storytelling Festival, the long-running Mount Dora Arts Festival, and the Central Florida Film Festival at Epic Theaters. If you happen to miss Renninger's Antique Extravaganza, which is so popular that it is held three times a year, stop by Renninger’s Twin Markets filled with antiques, flea-market finds, and other Florida oddities.
The town’s most iconic landmark is the 35-foot-tall Mount Dora Lighthouse on Lake Dora, part of the Harris Chain of Lakes. The brightly red and white-striped lighthouse with its white hexagonal lantern is the only inland freshwater lighthouse in Florida, and it still guides boaters safely around Lake Dora after dusk.
Gulfport
About 10 minutes east of popular St. Petersburg, Florida’s Sunshine City, you’ll be pleasantly surprised to discover the peculiar town of Gulfport. A warm, welcoming waterfront town, it is a must-visit destination for art lovers, writers, and musicians, with its highly walkable downtown area full of galleries, shops, and cafés, including local favorites like the North End Taphouse & Kitchen and family-owned Stella’s, where you can spend time socializing over drinks. The Village Courtyard is also a great place to treat yourself to flowers at Mildred Maloney Flowers and people-watch.
The small community’s most iconic celebration, its annual GeckoFest, takes place on August 30, 2025, with live music, street performers, and roving entertainers. Over 200 booths offer a variety of crafts, arts, and festival foods. Lead-up events to the big end-of-summer gecko bash include a Gecko Art Show, Gecko Crawl, and a costumed Gecko Ball. May the best-dressed gecko win.
Micanopy
Micanopy is Old Florida at its quintessential finest, with live oak trees draped in Spanish moss, which welcome you to the small town of around 700 residents. It’s a haven for antique hunters, pickers, and art collectors looking for original Florida Highwaymen paintings in the Micanopy OutPost on famous Cholokka Boulevard. The Highwaymen were a group of African American artists active in the 1950s-80s who bucked segregation-era barriers and sold vibrant artwork from the trunks of their cars. For treasure seekers looking for other one-of-a-kind pieces of art, be sure to include Antique City Mall and The Shop in Micanopy in your travels.
Cap off a visit to historic Micanopy with an overnight stay at the circa 1845 Greek-style Herlong Mansion Bed & Breakfast. Listed on the National Register of Historic Places, the mansion is reportedly haunted by the ghost of Inez Herlong, who inherited the property at the age of 68, walked upstairs to her childhood bedroom, and died there.
Dunedin
The west coast of Florida is a long way from Scotland, but that doesn’t seem to matter to the residents of Dunedin, a small town named after the capital of Scotland, Edinburgh. With its Scottish-themed downtown, home of the Scottish American Society of Dunedin, and shops like the Celtic Shop of Dunedin and Lothian Kilt Rentals & Bagpipe Supplies, everyone is a Celt in Dunedin. The town annually celebrates Scotland's heritage and culture with music, athletics, and a variety of Scottish-inspired food and drink every April.
Aside from the town’s peculiar Scottish connection, the town is a designated trail town where cyclists, hikers, runners, and rollerblade enthusiasts can share the 45-mile Fred Marquis Pinellas Trail, which runs from Tarpon Springs to St. Petersburg. Before hitting the trails, fuel up on craft beer and pub food at Florida’s oldest microbrewery, Dunedin Brewery.
Lake Placid
With nearly 50 outdoor murals, Lake Placid (not Lake Placid of Winter Olympic fame) is sometimes called the “Town of Murals.” An artsy town that pays homage to circus arts at the quirky American Clown Museum & School, where you can learn about the art of clowning. It is also known as the “Caladium Capital of the World,” and home to the annual Caladium Festival, which showcases the lush tropical plant known for its vibrant, heart-shaped leaves, at Stuart Park from July 25 to July 27, 2025.
For outdoor enthusiasts who love to spend time on the water, Lake Placid is smack dab in the middle of Florida’s “Lake Country,” with 27 named lakes in the area, including the 26,800-acre Lake Istokpoga, the 5th largest lake in Florida, and a popular black crappie and trophy-size largemouth bass fishing spot. Nearby Lake Jackson is also teeming with fish like crappie, bluegill, and catfish. Check out the local outfitter, Lake Placid Freshwater Charter and Guide, for information on a 6-hour day or night fishing excursion.
Carrabelle
Carrabelle is a small outdoorsy paradise on the Gulf Coast in the Florida Panhandle, in the scenic stretch known as the Forgotten Coast. Known for its pristine white-sandy beaches where you can swim, paddle, or book a fishing tour with local guide BustA-Knot Charters, the pretty seaside town is also renowned for being the home of the peculiar World’s Smallest Police Station. An old telephone booth used by the local police force in the mid-1900s, the station is now a roadside attraction, perfect for snapping IG-worthy selfies to post on your wall.
Another top attraction in Carrabelle is the Camp Gordon Johnson WWII Museum, which opened in 1942 and trained over 250,000 soldiers in amphibious operations. The museum’s unusual collection contains Japanese rifles, original operational plans, and the first Nazi flag obtained on German soil in September 1944.
Cassadaga
Welcome to the “Psychic Capital of the World,” also known as the unincorporated community of Cassadaga. Established in 1894 as the Cassadaga Spiritualist Camp by a New York medium named George Colby, this historic district was listed on the National Register of Historic Places in 1992. Filled with colorful Victorian cottages, spiritualist temples, and energy vortexes, it is one of the oldest active religious communities in the Southeastern U.S.
Known for its serene spiritual atmosphere, it encompasses seven private parks and meditation gardens spanning approximately 60 acres of land, with a reflective space sure to please everyone’s spiritual palate. A few notable spaces include Horseshoe Park & Fairy Trail, featuring fairy houses, trolls, and gnomes, as well as a giant selfie chair with wings; Seneca Park, a serene sanctuary with a gazebo dedicated to the spirit guide Seneca; and Medicine Wheel Park, which offers meditation and Native American-inspired ceremonies.
Matlacha
Near the ultra-vivid, rainbow-colored Leoma Lovegrove Gallery & Gardens, which showcases the artwork of renowned artist Leoma Lovegrove, Matlacha is a small seaside town that exudes the charm of Old Florida. Pronounced Matt-La-Shay, it seems like no coincidence that the town’s name rhymes with sashay, reflecting the laidback lifestyle of this creative town’s residents. Matlacha is part of a loosely connected archipelago of coastal islands, including Pine Island, the largest island, and Little Pine Island, a nature preserve between Matlacha and the mainland.
Take advantage of “island time” on the islands by beachcombing, shrimping, clamming, and visiting the Museum of the Island (MOTI). Or go full vacation mode, grab a table at the always-packed Yucatan Waterfront Bar & Grill, indulge in a classic Tiki Bar Mojito, and share a plate of Ahi Tuna Nachos, watching the waves roll in.
Fernandina Beach
Fernandina Beach is a small beachy community on Amelia Island, part of the Sea Island chain from South Carolina to Florida along the U.S. East Coast. Its claim to fame is being the hometown of Florida’s oldest bar, The Palace Saloon, but its historic district has garnered the town a spot on the National Register of Historic Places. Take a docent-led tour through the town’s 50-block district to discover Fernandina Beach’s past, which features pirates, Gilded Age millionaires, bootleggers, and an assorted cast of peculiar characters. Foodies flock to the island to fuel up at top restaurants like trendy eatery Wicked Bao, the Salty Pelican Bar & Grill, and Denucci’s for milkshakes, malts, floats, slushes, and old-timey banana splits.
A Quirky Trip To Florida
From Mount Dora’s festival-packed charm and iconic freshwater lighthouse to Gulfport’s funky waterfront vibe and wild GeckoFest, Florida’s quirky small towns pack a punch. Micanopy’s moss-draped streets hide haunted mansions and priceless Florida Highwaymen art, while Dunedin rocks its proud Scottish roots with kilts, bagpipes, and lively festivals. Lake Placid bursts with colorful murals and legendary caladiums, and Carrabelle surprises with pristine beaches and the tiniest police station you’ll ever see. Spiritual seekers flock to Cassadaga’s mystical Victorian village, Matlacha dazzles with rainbow-hued art, and Fernandina Beach serves up pirate lore in Florida’s oldest bar. These nine playfully peculiar towns in Florida prove that small doesn’t mean boring.
