10 Small Towns In Florida That Come Alive In The Fall
Strewn throughout the Sunshine State, these best fall destination towns promise clear days and warm temperatures where you can still hit the beaches in Venice and enjoy outdoor parks in Winter Park. From Mount Dora's two great lakes with the best bass fishing to swimming with the manatees in the Crystal River, there's even an alligator farm in St. Augustine!
Blending culture flawlessly into the fall-time nature under the warm Floridian sunshine, you can enjoy cozy outdoor pursuits and experiences in between the state's staple seafood and shopping scenes. Realize all your fall getaway dreams with this list, from ghost tours in time for Halloween to inspiring an international getaway in Tarpon Springs, a Greek coastal town, or Venice, a beautiful Italian city dressed in pink.
Crystal River
This quaint town near Central Florida's Nature Coast, overlooked in the summer heat for the coastal beaches, comes alive under the soft autumnal glow as a destination to swim with manatees. As the waters in the Gulf of Mexico get colder when the air temperatures drop in other states, its manatee population migrates to the pleasurably warm stream in the Crystal River. The springs, upholding a constant 72 degrees, blissful for all involved, relieve stress and relax your muscles after nature hikes through the intown Hunter Springs Park or the Kings Bay Park with water access because when the Florida sun still gets you down, you get in the waters! Even in January, you can enjoy the same warm waters and watch the manatee migration in action!
Beloved by the sun as much as nature-loving tourists and their kids, you can observe these comic creatures on a memorable family getaway from the dreary falltime city. The charming downtown area, replete with small-town businesses, welcomes you warmly to peruse and cozy up in the family-friendly atmosphere in between swimming along these gentle giants in the springs, as one of the only places in the country with such a unique nature interaction. The Plantation on Crystal River, with stately white buildings and real Southern charm, promises a fun day exploring on a stroll, with water pursuits, golf, and fine dining against a glorious sunset over the river.
Dunnellon
This north-central small town of just under 2,000 residents sits in a very fall-worthy region to visit, with other cozy towns like Ocala just east and Homosassa just south. Ensconced in the scenery along the Rainbow and Withlacoochee rivers, Dunnellon is nothing short of its "Treasure of the Nature Coast" nickname. With two rivers, you will never run out of activities under the sun, like kayaking and fishing for over two dozen varieties of fish, including some real big bass, while saving the nearby towns for a rainy-day drive-over to peruse more local hotspots.
While other states brace for the cold winds and early snow, you can spend days outdoors, with warm weather here lasting through the fall. From river strolls and picnics to immersive nature hikes through Rainbow Springs State Park with its beautiful trails, you can also go paddling, tubing, and swimming within a painting-like scenery of an autumnal color palette. Afterward, the highest-rated tourist and local favorite, Swampy's Bar & Grille, perched over the river, offers a cozy outdoor setting under blue umbrellas with water views from above.
Gulfport
The charming town of Gulfport, with its picturesque waterfront, fishing history, and art along the streets, promises a rollicking time for everyone in your family on a fall-time visit. This hidden, happening hippie enclave, just under three square miles in area, boasts the Village District as its heartbeat, brimming with independent shops, boutiques, and eateries along the brick-paved streets. The canopy of moss-draped live oaks follows you like vibrant halos above your head, mimicking the quaint, candy-colored cottages around you on a stroll with unobscured views of the waters. From the legendary weekly farmers market to the jutting 500-foot pier, there's also a groovy sculpture park.
With easy access just west of St. Petersburg and Treasure Island Beach Resort, the town in the shadow of the popular Tampa/Clearwater area stays crowd less for an intimate getaway with your loved ones. You can enjoy browsing through the colorful lineup of boutiques along Beach and Shore Boulevards, the heart of the historic downtown with views of Boca Ciega Bay. Void of parking meters and chain stores, but just the perky locals who call their home a "small town with a big heart," Gulfport was also the "best food town" in the United States. The eclectic dozen eateries do Rand McNally's claim justice, including the vegetarian deli at Golden Dinosaurs and Mediterranean cuisine at Neptune Grill.
Matlacha
Matlacha, a real one-time wonder from every angle with more than a pocket full of centuries-long heritage, is pronounced Mat-la-SHAY or "Big Warrior" in Seminole. This really cool island town with a distinctive hair-comb shape is connected to the mainland via the Matlacha Pass Bridge and all the way to Pine Island on the other side. Its old fishing village vibe since the turn of the last century comes out through the timeless Old Florida charm and a laid-back local lifestyle in the present-day artists' enclave. Home to just over 800, the waterfront town of artisans and fishermen is great to explore on a stroll or a bike ride in the pleasant falltime weather.
You can start along the main stretch at The Perfect Cup before spending an afternoon at the big Matlacha community park with cycling and walking paths. With streets full of art and a quirky spirit along the craft stands and colorful mobile homes, there are plentiful local shops to peruse for gifts and fresh seafood markets with more bohemian vibes. Discover the island's unique and eccentric homes on a walk through the streets along the "comb" bristles, and then back to the notable Blue Dog Bar & Grill for dinner and a sunset view from the shores before hitting the local bar scene.
Micanopy
With over 200 years of history in its pocket, Micanopy is Florida's oldest inland town and the self-proclaimed antique capital of the state. Named after a Seminole Indian chief and first settled in 1821, it is a 15-minute ride south of Gainesville for a getaway full of nostalgic vibes. The nearby Paynes Prairie Preserve State Park is the best place for active nature fans, with trails and free-roaming wild horses and bison, you can observe below after climbing the 50-foot-high tower.
The charming oak-lined Cholokka Boulevard, verdant through the fall, is a joyous sight on a vintage shopping spree through the hot lineup of boutiques and the annual Fall Harvest Festival, which unravels in art and music right here. Abundant in more than just antiques, there are happening cafes and thriving art galleries to visit, from Delectable Collectables to the Micanopy Historical Society Museum. You can recharge at the aptly named Old Florida Cafe or hit the popular, highly rated Pearl Country Store & Barbecue along Hwy 441 for dinner.
Mount Dora
Mount Dora, just an hour from Orlando, is a memorable day trip or weekend escape from the "Orlando-ness" to "fall" into laid-back vibes and relaxing pursuits. With Lake Eustis to the north and Lake Dora south of downtown, you can enjoy swimming in the still-warm waters and sightseeing at the iconic lighthouse in Grantham Point Park for an Instagram shot. Wisely take advantage of being in the "Bass Capital of the World" with a fishing rod in the serene fall nature. As a designated trail town with everything from mountain bike trails to parks, its lakes with lakefront amenities include boat rentals for daytime launches and the scenic Palm Island Boardwalk for sunset strolls.
You can experience all the pleasures of the bucolic Old Florida lifestyle amid quiet bed and breakfasts, country inns, and a lineup of tasty dining options, including outdoor cafes, gourmet restaurants, and wineries. From its 100-year-old historic village to an annual event unraveling along the waterfront or an antiquing day in the city center, there's something for everyone in Mount Dora. For a cozy fall day, stop at the old railroad station under timeless charm while browsing through the trendy valuables, antiques, and collectibles downtown.
St. Augustine
St. Augustine, the longest continuously inhabited European-founded city in the entire US, gets into its falltime attire like no other town in Florida. The town along the Atlantic coastline would not be South Florida without a beach, and St. Augustine has the finest one for paddleboarding and sailing, as well as more water adventuring on a kayak along an inland waterway. Scavenge for sights and attractions without crowds for unobscured views of St. Augustine Lighthouse, while wild animal interactions at the Alligator Farm and a bike ride through the natural Anastasia Island State Park with rich flora and fauna will make your nature-loving heart ecstatic. Founded by Don Pedro Menendez de Aviles of Spain in September 1565, the "Nation's Oldest City" will soon be turning half a millennium old!
St. Augustine is a walkable town with narrow streets lined by countless cultural gems like museums and historic landmarks, including the iconic Castillo de San Marcos. Having changed hands many times between Spain and Britain, European sights prevail in famous forts, the Colonial Quarter, and Greek influence. From Ponce de Leon's "Fountain of Youth" to the Oldest Wooden Schoolhouse, you can spend days discovering rich history before diving into 21st-century attractions like paranormal ghost tours downtown in time for Halloween or a professional golf course. There's also shopping along the cobblestoned historic St. George Street to the upscale Ponte Vedra Beach and farmers' markets before fine dining on the day's fresh catch with water views.
Tarpon Springs
There's plenty of fish in Tarpon Springs' waters, after which this shore town along the Gulf of Mexico was named. Just 45 minutes north of St. Petersburg, Tarpon Springs feels like a Greek coastal town you can enjoy without crowds in the fall along all of its 51-mile waterfront allure, with the moniker "sponge capital of the world." From fishing in the abundant waters to learning about the rich sponge diving history initiated by the Greeks and still prevalent to this day, Tarpon Springs is a longtime destination for Greek immigrants and expats.
You can revel in their most potent gift of Greek food offerings, particularly along the Dodecanese Boulevard, like the highest-rated Mykonos or Dimitri's on the Water. Downtown Tarpon Springs, on the National Register of Historic Places, is a charming blend of old and new, Greek and Americana, with art galleries, antique stores, and specialty shops within 1800s buildings. The renowned Tarpon Springs Performing Arts and Cultural Center promises many falltime evenings getting acculturated over a theater performance, a concert, and other quality programs amid more art and historical exhibits.
Venice
This town along Florida's white-sanded Gulf Coast is not just "nice" for a summertime beach escape, but "Ve-nice," an exclusive getaway in the shoulder season just south of Sarasota, with almost no tourists to enjoy its pristine 14-mile stretch in serene nature. From Casey Key to Manasota Key, you can beach comb for miles while shelling, a favorite local pastime in Venice, to a new lounging place each day with recreational opportunities like swimming, sunbathing, fishing, and boating until spectacular sunsets.
While you sift through the sands for the abundant fossilized shark's teeth to take home as a unique keepsake or souvenir for a friend, golf lovers can enjoy their favorite pastime with excellent courses in the greater Venice area. As the Main Street City in the Sunshine State, Venice's downtown is a graceful centerfare, originally planned in 1925, comprising fine Italian architecture and beautifully landscaped boulevards—a joy to the eye. Enjoy the atmosphere akin to a real Italian city along Venice Avenue with pink Italian Renaissance buildings and the best-unobscured views to capture it all without crowds during the fall.
Winter Park
Just 20 minutes northeast of downtown Orlando, Winter Park is a favorite year-round escape from "Orlando-ness," but no list of fall Florida getaways can be complete without it. Named after the South Florida Railroad in 1880 and the educational institute for higher learning opening shortly after, Winter Park thrived thereon while retaining a small-town feel with around 30,000 residents and a walkable downtown area. Its robust park system and the gorgeous Winter Park Chain of Lakes offer trails and verdant lands, along with water access. Full of parks to enjoy in the fall without crowds, Park Avenue, the tree-lined, cobblestoned heartbeat of the city, is chock full of acclaimed eateries, museums, and shopping areas rivaling Orlando's.
More than just a suburb, Winter Park is an arts and culture destination in its own right, with a small-town feel near the Disney scene that feels guarded against all the Mickey ears and replete with cultural institutions for cozy fall-day wanderings. The highly rated Rollins College, Florida's first four-year university to visit, owns the Charles Hosmer Morse Museum of Natural Art—both worthy visits. When you stay at one of The Alfond Inn's 112 tremendous guest rooms, what you pay directly benefits the scholarship program at Rollins, while you get a full range of amenities, a pool, and a riveting art collection to view.
Just imagine Florida's already glorious nature getting its gems dressed up for the fall season of pumpkins and giving thanks. You don't have to imagine or worry about being too late, but start packing your bags for these destination towns, which readily welcome fall enthusiasts after the heavy summer stampede with great places at fair prices.
These ten historic towns are year-round destination getaways from the city, including the oldest European settlement in the US, St. Augustine. With many towns along the Nature Coast, like Crystal River and Dunnellon, you will be steps away from the downtown to quintessential experiences like swimming with manatees that escape the colder Gulf of Mexico waters to Crystal River.
