12 Historic Small Towns in Florida to Visit This Weekend

We know Florida is mostly known for its white sandy beaches, tourist-magnet theme parks, and, well…Miami. But charming small towns in Florida boasting history, natural beauty and Southern charm, are also worth visiting.

Although not often part of a Florida travel itinerary, these small historic towns can offer a quieter and more unique travel experience that evokes a certain appeal for those seeking it. 

These are places where character and charm seem to be in every corner, be it in the picturesque streets of towns like Micanopy, cute beach towns like Fernandina Beach, or the more popular and quaint small towns like Mount Dora. 

Historic Daffodale House in Monticello, FL
Historic Daffodale House in Monticello, FL

Add These Quaint, Historic and Small Towns in Florida to Your List

From outdoor adventures to cultural festivals to unwinding in a laid-back ambiance and inspiring historical experiences, these small towns in Florida have a lot to offer—without the hefty admission fees (wink, wink)

1. Micanopy

Believe me when I say that walking the streets of Micanopy is like stepping back in time! Often called “The Town that Time Forgot,” Micanopy is one of those one-of-a-kind, quirky small towns in Florida that feels like a living, breathing history book—rightly so!

Cute antique shop in Micanopy that looks like a red barn
Cute antique shop in Micanopy

Founded in 1821, Micanopy is considered Florida’s oldest inland town. Most of its charm lies in its unspoiled historic district, laid-back atmosphere, antique shops and intriguing history.

As you walk down Cholokka Boulevard, there is a good chance you will fall in love with the Old Florida vibes and cute, historic homes—one of the most beautiful being the Herlong Mansion Bed & Breakfast, placed on the National Register of Historic Places. 

Right across from the mansion is the Church of the Mediator—a beautiful, historic church in Micanopy outlined by moss trees and an eye-catching red door. Just a brief walk from the church, you can visit the Micanopy Historical Museum, which opens Wed through Sun from 1 pm to 4 pm.

Historic buildings and antique shops in Micanopy
Historic buildings in Micanopy

Micanopy is one of the best small towns for antiquing, self-guided tours, and delicious Key Lime Pie and the best Cuban coffee you will ever taste! 

Everywhere you go feels like a scene from some novel or history book beneath moss-draped oaks. Surely, Micanopy’s historic district makes this a great town to experience the true notion of rural Florida charm.

2. Sopchoppy

I’d never even heard of Sopchoppy until we spent a weekend at Wakulla Springs. This small population town is located in the heart of the Florida Panhandle and it’s known for its annual Worm Gruntin’ Festival. And yes, I’m talking about worms.

Historic Sopchoppy Train Depot & Museum
Historic Sopchoppy Train Depot & Museum

Basically, the art of worm grunting, or worm charming, is when vibrations are made on the ground with a stake, making the worms come out to the surface to be collected and sold for bait.

Incredibly, this worm festival pulls in hundreds of visitors every year, taking place on the second Saturday of April. 

For things to do in downtown Sopchoppy, you can visit the local brewery Civic Brewing Co., where there’s hipster music and good beer—which Carlos loved!

Carlos and I outside Civic Brewing Co. in Sopchoppy
Carlos and I outside Civic Brewing Co. in Sopchoppy

Heading a bit across from the brewery is the Historic Sopchoppy Depot—the only depot from the GF&A (Georgia Florida & Alabama Railroad) still remaining in Florida. Today the Depot is a museum, and it’s mostly open on Saturdays.

Also nearby is the Apalachicola National Forest, which is an ideal destination for nature lovers with its wide variety of wildlife and beautiful hiking trails

With a population of just about 470, the laid-back vibes and friendly locals make Sopchoppy a great place to experience the ‘Real Florida’.

3. Tarpon Springs

Known as the Sponge Capital of the World, the charming town of Tarpon Springs is full of Greek Culture and picturesque views. We loved that it’s a very walkable town and you can explore plenty of it in one full day. 

tarpon springs sponge docks
Historic Sponge Docks in Tarpon Springs

The main attraction is the historic Sponge Docks, and if you’re lucky you’ll be able to see the sponge divers at work. Sponge shopping, indulging in authentic Greek cuisine at waterfront tavernas, or taking a scenic cruise along the Anclote River are also some of the top things to do in Tarpon Springs.

If you’re into festivals and culture, don’t miss the annual Sponge Docks & Craft Festival in April, the Tarpon Springs Seafood Festival in November and the Annual Epiphany celebration in January.

Without a doubt, Tarpon Springs is one of the cutest beach towns near Tampa that you can visit any time of the year!

4. Mount Dora

This is one of Central Florida’s most picturesque towns with a combination of Southern hospitality and small-town charm that makes it one of the most visited small towns during the holiday season. 

Cute white buildings surrounding Sunset Park in Mount Dora
Cute white buildings surrounding Sunset Park in Mount Dora

The streets of Mount Dora Historic District are lined with boutique shops, galleries, nice restaurants like the popular Las Palmas Cuban Restaurant and cozy cafes and tea shops.

As one of the must-visit places, the Mount Dora Marketplace should definitely be added to your list. This multi-vendor indoor market features cute little shops, bars, local eateries and even a brewery—Wolf Branch Brewing.

Another popular spot in town is Sunset Park; home to the 40-ft iconic Christmas Tree, Photos with Santa and the center for soaking in the small-town vibes. Right next to Sunset Park, you’ll see the Railroad Depot which is an interesting spot for those who enjoy bits of history from old train stations.

crossing the street to the Mount Dora Marketplace
Tourists crossing the street toward Mount Dora Marketplace

Other things to do in Mount Dora include the Mount Dora History Museum, a ghost tour of Florida’s oldest continually running hotel—the Lakeside Inn Hotel, or a scenic pontoon boat tour along Lake Dora and the Dora Canal. 

For a relaxing nature walk, don’t miss the Grantham Point Lighthouse and the Palm Island Boardwalk Trail.

This picturesque town in Florida hosts many festivals and happenings year-round, such as the Mount Dora Arts Festival and the Light Up Mount Dora Holiday Celebration and Boat Parade.

As one of the most family-friendly small towns in Florida, a visit to Mount Dora can be a truly joyful experience for travelers of all ages.

5. Auburndale

Situated halfway between Orlando and Tampa, Auburndale is a quaint small town best known for its scenic lakes and citrus groves. A quiet historic district lends this picturesque town its flavor, along with architectural gems and cultural heritage. 

the historic Auburndale City Hall
Auburndale City Hall, a national historic site. Fun fact: there is a time capsule buried here, to be opened on July 4th, 2076.

One of the most decorative landmark icons is the City Hall—a national historic site. The Auburndale City Hall is located in the heart of the town’s historic district and stands as a feat of Italian Renaissance Revival architectural style.

Right nearby, you’ll find the Auburndale Old Seaboard Air Line Depot, now a landmark but served as a vital transportation hub back in the day.

You’ll also see The Historic Baynard House which closely touches the spirit of Folk Victorian architecture and is one of the most beautiful historic houses in Auburndale.

The Historic Baynard House, circa 1894
The Historic Baynard House, circa 1894

Some of the other must-see historic buildings of this small Florida town that I really loved were the Baynard Retail Building built around 1926 and the Triangle Building, a “Flatiron” building built around 1912.

Being a lover of historic buildings, the charming historic district in Auburndale would get me going on and on about it being one of the cutest small towns in Florida.

6. Brooksville

My first visit to Brooksville was years ago now while wandering around Florida’s Nature Coast in search of outdoor points of interest.

It’s in this part of Florida where you’ll find Brooksville, a small quaint town known for its Southern hospitality and historic charm. 

Hernando County Courthouse in Brooksville
Hernando County Courthouse in Brooksville

As you walk the streets of the Historic Downtown District of Brooksville and stroll down Main Street, you will find cute local shops, eateries, and many historic buildings with a rich history.

The Brooksville self-guided tour, in which you can scan QR codes at each of the historic buildings, like the 1885 brick Grimsley Country Store, is one of the best things to do if you love historic small towns.

Among the most beautiful buildings is the Hernando County Courthouse, placed on the National Register of Historic Places, and built in 1913.

Nature lovers and outdoor enthusiasts can visit the Withlacoochee State Forest, voted by WWF (World Wildlife Fund) as one of the “10 Coolest Places You’ve Never Been in North America.”

It’s an amazing outdoor destination for hiking, biking, canoeing, and horse riding through these beautiful wetlands and forests.

may stringer house in brooksville florida
The historic May-Stringer House in Brooksville. Fun fact: there are two time captures buried here.

Important historic sites in Brooksville that you must not miss include Chinsegut Hill, the May-Stringer House, and the Brooksville 1885 Railroad Depot Museum.

Another classic, of course, is Coney Island Drive Inn, where even Elvis Presley himself came to try their iconic foot-long hot dogs as he was shooting a movie in Inverness back in 1961!

With small-town charm and natural enchantment, Brooksville is the go-to place for outdoor adventurers and lovers of Old Florida towns.

7. Key West

It is, in fact, the southernmost point of the United States; however, it’s also on the right side of that dang Seven Mile Bridge!

Duval Street, Key West
Duval Street, Key West

But the 10-minute drive on this daunting bridge leads you to Key West—one of the coolest small towns in Florida with an eclectic mix of history, art, and laid-back vibes. So if you ask me, I’d say it’s worth the drive!

Despite being known for its tropical appeal, Key West has an inviting cultural history with historical landmarks like the Key West Lighthouse, Ernest Hemingway’s House (six-toed cats included) and Sloppy Joe’s.

In this beautiful island town where you can walk down Duval Street—the main street in Key West, famous for its eclectic shops, art galleries, vibrant nightlife and culture.

But one of the most popular things in Key West is the Sunset Celebration at Mallory Square. As one of the best places to see the sunset in Key West, it’s a well-known celebration and the best sunset spot in town since the ‘60s! 

For art lovers, some of the best galleries include Art@830 just off the Key West Harbor, Gallery on Green and Key West Gallery.

the gothic-style Rockhouse Gallery building in Key West
Rockhouse Gallery building in Key West

And if you’re a history buff like myself, you’ll have a great time visiting places like the Harry S. Truman Little White House, San Carlos Institute La Casa Cuba,” the Southernmost House, and Curry Mansion, the home of Florida’s first millionaire William Curry. 

Last but certainly not least, for our large group of readers who like to explore haunted places, you can visit Robert the Doll— the most haunted doll in the world.

The current home of Robert the Doll is the Fort East Martello Museum where you can book the Ghost Tour and Robert the Doll Experience or take a quick look during your regular museum visit.

8. Apalachicola

Sitting right on the Apalachicola River, where it meets the Gulf of Mexico, Apalachicola is one of Florida’s most delightful small towns.

Founded in 1821, Apalachicola was once one of Florida’s main cotton shipping towns and one of its busiest port towns.

Some lovely brick buildings fill this Historic Downtown area of this Antebellum port town, including the delightful Dixie Theatre. Seafood restaurants line the brick-paved streets, serving fresh oysters coming from the waters of the neighboring Apalachicola Bay. 

Among the top things to do in Apalachicola, the John Gorrie Museum State Park honors the inventor of the first ice-making machine, who was also the town’s most famous resident. 

Outdoor enthusiasts can enjoy airboat adventures, fishing trips, and kayaking on the Apalachicola River

If you enjoy cultural events and festivals in small towns, you can visit the Florida Seafood Festival which takes place in November at Battery Park. 

With its laid-back atmosphere and scenic waterfront views, Apalachicola can be the perfect destination for a quiet and relaxing getaway.

9. Cedar Key

Another charming small town, but this time on the Florida Gulf Coast and located southwest of Gainesville, is Cedar Key.

This place is reputed to be low-key, full of natural beauty and with fewer than 800 residents, making it a great place to get off the beaten path.

You can explore the quaint shops, art galleries, fishing shacks and seafood restaurants. Take a stroll along the waterfront and watch the sunset over the marshes and mangroves. 

This small, quiet town is Old Florida in its remoteness and slower way of life. Cedar Key area is widely recognized for its wildlife. Being a haven for many species of birds, Cedar Key is a paradise for birdwatchers, photographers, and nature enthusiasts.

Among the most popular things to do in Cedar Key are the Old Florida Celebration of the Arts in April, the Pirate Festival in November, and in February, the Stargazing Party

10. Crystal River

Crystal River isn’t just the heart of Florida; it’s the very soul of the Nature Coast! This Old Florida gem marries a rich bounty of natural beauty with an engaging cultural history. 

Crystal River Old City Hall
Crystal River Old City Hall

More importantly, this is one of the most ideal small towns in Florida for outdoor lovers and anyone looking for a unique lifetime experience.

Crystal River is known for its huge, spring-fed waterways with one of the greatest concentrations of The Florida Manatee (subspecies of West Indian manatees), and it’s the only place in the U.S. where swimming with manatees is legally permitted.

More than just the draw of manatees, Crystal River has its backstory and it’s a great place to become acquainted with the area’s ancient past. You can start by stopping at the Coastal Heritage Museum located in the historic Crystal River Old City Hall building.

Crystal River Archaeological State Park
Crystal River Archaeological State Park

Another not-to-miss place to visit is the Crystal River Archaeological State Park—a National Historic Landmark, where you can walk among impressive burial mounds

With its constant mild climate, Crystal River is perfect at any time of year for the great outdoors, whether it’s fishing, birding or hiking.

What makes Crystal River special is the combination of wildlife and historical heritage, which creates not just an incredible small town to visit but a place to connect with nature and history.

11. Fernandina Beach

As the main town on Amelia Island, Downtown Fernandina Beach has a really nice blend of historic quaintness with a relaxed beach atmosphere. This is a great beach town to walk around the marina and enjoy the scenic views.

historic buildings in fernandina beach florida
Historic Buildings in Fernandina Beach

It’s also a great place if you love historic sites. There are numerous historic buildings built in the 1800s, cute shops, eclectic restaurants, and, of course, lots of sea breeze. 

One of the most prominent historic sites in the Fernandina Beach Historic District is The Palace Saloon, a historic pre-prohibition era bar built in 1878 with all the picturesque charm worthy of pictures. 

If you’re a history and nature lover, you’ll find many things to do in Fernandina Beach.

For starters, you can visit one of the most scenic and best-preserved forts in the country—Fort Clinch, a Civil War-era fort built in 1847.

At Fort Clinch State Park you can see reenactment events, take candlelight tours and go to the beach via their boardwalk access.

Passing through the tunnel at Fort Clinch State Park
Really old pic of my boys passing through the tunnel at Fort Clinch State Park

Other top things to do in Fernandina Beach for history buffs include the oldest lighthouse in FloridaAmelia Island Lighthouse, just down the road from Fort Clinch, the Amelia Island Museum of History and Fernandina Plaza Historic State Park

If you’re looking for relaxing things to do in Fernandina Beach can check out the Amelia Island Historic Tours and the Sparkling Light Tour during the holiday season.

There are also several festivals on Amelia Island, including the Les DeMerle Amelia Island Jazz Festival and the Isle of Eight Flags Shrimp Festival.

A cool fact about this small coastal town on Amelia Island is that they have an Accessible Travel Guide that provides great options to families and people traveling with wheelchairs or any other special need. 

Sunset on Amelia Island
Sunset on Amelia Island

I recommend a stop by the Welcome Center in the former railroad depot to experience first-hand all that there is to do and see in and around Amelia Island, especially if you plan to visit for the weekend or a week-long stay. 

Undoubtedly, Fernandina Beach on Amelia Island is one of the quaintest small towns in Florida and an ideal destination for history and beach lovers alike!

12. Monticello

We’re now at number 12 on our list. If by now you’re still itching to find that so-called true old Southern charm of the small towns in Florida, then Monticello will be it for you! 

Monticello Opera House, circa 1890
Monticello Opera House, circa 1890

Located in Jefferson County, just a short drive from Tallahassee, Monticello is Florida’s third oldest historic district with more than 600 historic buildings, with many of these listed on the National Register of Historic Places, making it the place to be for lovers of historic sites. 

Just a few of the beautiful historic structures in Monticello include the Denham-Lacy House, most commonly known as the 1872 Denham Inn, Budd-Pafford House (circa 1833) and the Avera Clarke House (circa 1890). 

With the oak-lined canopy roads, the Opera House (circa 1890), antique shops and that iconic Jefferson County Courthouse right in the center of the town, there’s as much history as there is southern charm! 

The Denham-Lacy House, commonly known as the 1872 Denham Inn
The Denham-Lacy House, commonly known as the 1872 Denham Inn

Nevertheless, before going on a search for things to see, I recommend making your first stop at the Monticello-Jefferson County Chamber of Commerce, housed in a historic building built in 1917 that was the first Catholic Church in the county. 

Here, you’ll want to grab a free copy of the Walking & Driving Tour Map and these are located in a little box right outside the door. If you have a full day for visiting Monticello, then you can probably do both the walking and driving tours.

Monticello-Jefferson County Chamber of Commerce
Monticello-Jefferson County Chamber of Commerce. This is where you will grab your free walking tour maps!

The quaint town of Monticello is also home to the Annual Watermelon Festival in June, a tradition since 1949 with parades, bed races, pageants and more. 

And not that I’m intentionally saving the best for last, but word gets around that Monticello is the most haunted small town in the south…which means…haunted experiences!

The Moonlight Cemetery and the Victorian Haunted History Tours are offered only by reservation and you can contact Historic Monticello Ghost Tours for reservation and more info.

🗺 Which of these small towns in Florida would you love to visit or which one is your favorite? Let us know in the comments!

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Yanitza Ninett
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Yanitza is an avid adventurer with 15+ years of hiking experience and outdoor travel. As a PADI-certified scuba diver, she's also passionate about ocean conservation. When she's not exploring the great outdoors, Yanitza obsesses over The Vampire Diaries and dreams of traveling to Mallorca, Spain.

10 thoughts on “12 Historic Small Towns in Florida to Visit This Weekend”

  1. Rural Florida certainly has its unique charms! The Worm Gruntin’ festival made me laugh, and I think I need to see this in person. Good to know the drive on the Seven Mile bridge is worth it. Great details, thanks for sharing!

    • Thank you so much for reading! Yeah, when the locals in Sopchoppy told us about the Worm Gruntin’ festival, I couldn’t believe what I was hearing lol! It’s quite the unexpected and interesting thing to exist 😂

  2. I love finding quirky towns. I’ve only been to Florida once and of course the only place I visited was Miami. I never heard of any of these before but that’s what I love – finding hidden gems.
    I’d love to visit Mount Dora, I don’t think I’ve experienced “proper” southern hospitality so it’ll be such an experience, also paying a visit to the indoor markets would be a treat 🙂

    • Mount Dora is a great small town for a first-time experience. It has all the quaint and charm but it’s also adaptable to those looking for a more ‘touristy’ feel.

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