Bicycling around Old Florida: Six Trail Towns in 13 days

Last updated on November 6th, 2025 at 11:29 am

Our guest writer Patty Huff is a bicycle advocate who has bicycled across the United States twice and throughout Europe. Here’s her account of a vacation exploring and biking in Florida’s Trail Towns.

For the past 26 summers my husband and I have spent our vacations biking. This year we chose to drive and bike around Old Florida, stopping in as many Trail Towns as possible.

A Trail Town is a place where people “can venture off a hiking, biking, equestrian or paddling trail to enjoy the amenities and unique heritage of the community.” It’s a program administered by the Florida Office of Greenways and Trails to encourage people to visit some of less visited Florida’s small towns.  Florida currently has 21 Trail Towns.

On our August trip, we pedaled about 150 miles. We bike early in the morning before it gets too hot. Many of the trails were shaded and when you’re biking, you don’t notice the heat if you keep pedaling, only when you stop. We wear lightweight long sleeves to avoid sunburn.

After attending the Florida Greenways and Trails Foundation and the Office of Greenways and Trails Council meetings this summer in Sanford, I decided this recently designated Trail Town would be a great place to start.

Cycling Sanford area and its springs

We found an Airbnb in the historic district for three nights as we explored the area. On the first day we cycled 35 miles, starting at the downtown Riverwalk, then west to DeBary (another Trail Town), out to Green Springs, back to Gemini Springs and a return to Sanford along shady pathways. The springs were incredibly beautiful with lots of foliage.

Florida Rambler’s guide to Sanford, and the River of Lakes Heritage Corridor, which include De Bary, Green Springs and Gemini Springs

At the Sanford Visitor Center, housed in the original post office, I picked up my first Trail Town sticker. The following day we cycled to the Cross Seminole Trail and over I-4 to the Seminole Wekiva Trail, a 38 miles round trip. We enjoyed beautiful sunny days for cycling with our evenings spent walking around town, enjoying delicious dinners at Hollerbach’s, The District, and the Old Jailhouse.

Florida Rambler guide to the Seminole Wekiva Trail

White Springs, Florida’s first big tourist mecca

The next town on our itinerary was 3½ hours northwest to White Springs on the banks of the Suwannee River and home of the Stephen Foster Folk Culture Center State Park. We spent a few hours touring the museum, the bell tower, and cycling around the state park. The next day we biked to Big Shoals State Park where we had access via the Little Shoals entrance to the 6.8-mile round-trip paved Woodpecker trail through the forest.

Florida Rambler’s guide to White Springs and the Stephen Foster Culture Center State Park

It is difficult to imagine that this sleepy little town was the first major tourist destination in Florida. Grand hotels greeted thousands of visitors from all over the world who came in the 1800s and 1900s for the healing powers of the local mineral springs. After the 1911 fire that swept through town, only one hotel (the Telford) survived; today it is a private residence.

The visitor center is now closed (due to lack of staff we were told) but the 1885 Suwannee Hardware & Feed Store has lots of information and the place to get a Trail Town sticker. We stayed at the historic White Springs B&B, owned and operated by Judith for the last 19 years, hosting long-distance cyclists.

A quick drive through Jasper, the Hamilton County seat, then just two hours by car to the historic fishing village of St. Marks. The cycling options are many:  bike 32 miles roundtrip on the historic railroad trail to Tallahassee, or miles and miles on the Big Bend Scenic Byway Coastal Trail along Hwy 98, or the 28-mile round-trip to St. Marks Lighthouse which we did. (If you go, be sure to check out the lighthouse’s living quarters and talk to the keeper of the lighthouse.)

Florida Rambler guide to St. Marks and the Big Bend Scenic Byway

 Also, along this route, is the San Marcos de Apalache Historic State Park where you will learn about the Muscogee Tribe, the 17^th century Spanish Florida occupation, and the Civil War period.

Dinner was enjoyed at the Riverside Café listening to a local band. We found comfortable accommodation at the nearby Shell Island Fish Camp. During our stay we took a quick side-trip to Sopchoppy to meet friends for dinner at the Civic Brewery Company for a great pizza and beer. We first discovered Sopchoppy about 15 years ago when we cycled there from Tallahassee on our way to St. George’s Island. Thankfully, it hasn’t changed much but is recognized now as a Florida State Trail Town and has several new businesses.

Our next stop along the coast was the Old Carrabelle Hotel in the historic district of Carrabelle. The bike shop there had recently closed, but we found a lot of information and history at the museum across the street in the original City Hall. The museum has artifacts from centuries ago and memorabilia up to the present time – treasures from Old Florida. We enjoyed a delicious lunch at the Fisherman’s Wife restaurant, dinner at Evenin’ Bite, and breakfast the next morning at the historic Carabelle Junction Café.

Time to move along the coast to San Blas and Port St. Joe (delaying a stop in Apalachicola until our way back). San Blas is out on the St. Joseph Peninsula and has been developed with stilt houses until you reach the state park at the end of the road.

It was wonderful to bike through this secluded state park area, stopping at the wide white sandy beaches where there were few visitors during the week at this time of year. We then drove to Port St. Joe and stayed overnight at The Port Inn & Cottages, conveniently located across from Reid Avenue in the historic business district where we found The BrickWall Sports Bar & Grill and the Provisions Restaurant, both excellent. Sunset at the Lighthouse across the highway on the Gulf was spectacular. Our cycling time was spent exploring quiet neighborhoods along rural roads.

Wewahitchka to Milton

We took another quick deter to Wewahitchka, just 24 miles north of Port St. Joe, and discovered it was the location for the movie “Ulee’s Gold,” the 1997 film starring Peter Fonda about a beekeeper. I love Tupelo honey so was very excited to find some at Lanier’s, home of the “bee consultants” for the film.

We continued back south from Wewahitchka to Mexico Beach, then Panama City, and west along Highway 98, arriving in Milton (another Trail Town), just northeast of Pensacola. We visited a bicycle shop along the Blackwater Heritage Trail who advised us to stop at the visitor center not far up the trail to get a sticker and information. Unfortunately, it was closed when we arrived around 3:30 pm and, with a thunderstorm developing, we thought we would stay the night and bike early the next morning. However, the only lodging we could find was close to I-10 interstate with not a lot of options for a good dinner. Instead, we made the decision to drive to Navarre for the night, enjoying a good meal at the Emerald Waterfront Bar & Grill.

Florida Rambler guide to Milton area

Apalachicola for the Old Florida we don’t always find

 Rather than returning to Milton, we drove 3½ hours east back to Apalachicola where we had stayed many years ago at the Riverwood Suites, conveniently located on Ave F and just a few blocks from Up the Creek Raw Bar. We had a wonderful dinner on the deck with the best view of Apalachicola Bay. There are several eateries in town that offer wonderful seafood, coffee, desserts, etc. Biking was through the quiet neighborhoods; it’s a beautiful town that appreciates historic preservation – the Old Florida we continue to seek, and sometimes find.

Florida Rambler guide to Apalachicola

High Springs for small town charms

Three hours southeast we stopped in High Springs, a small town known for its many antique shops. They have two visitor’s centers, one (located on Main Street) with information about the nearby springs and the Chamber of Commerce, which is housed in the old depot building. The only bike shop, we were told, is now closed.

Florida Rambler guide to High Springs and paddling the Santa Fe River

Lodging was limited to two small motels just north of downtown but close enough to bike the area. We stayed just one night before heading to Clermont, located along the Coast-to-Coast Trail.

Clermont offers miles of good trails

Historic Clermont, situated on the south end of Lake Minneola, is another Trail Town with cycling opportunities. The Hancock Trail intersects with the South Lake Trail which connects to the West Orange Trail, forming a 36-mile continuous pathway. We stopped by City Hall and a local bike shop before picking up our Trail Town sticker at the Arts & Recreation Center at 3710 South Hwy 27 on our way out of town.

Florida Rambler guide to West Orange Trail area

Home to Everglades City

 After 11 days on the road, it was time to head home to Everglades City, our last Trail Town.

Florida Rambler guide to Everglades City

We had accomplished what we set out to do – visit the Florida’s Trail Towns that we had not been to before and experience Old Florida by bike.

For all the years of cycling in Florida, we have experienced 18 out of the 21 designated Trail Towns (the last three – Malabar, Vilano Beach, and Deltona – we plan to do on our next journey).

The Office of Greenways & Trails has distributed little booklets titled “Explore Florida Trail Towns,” which are available in every Trail Town, encouraging visitors to get a “sticker” from each town.

At our Welcome Center in Everglades City, we keep these booklets out on our desk along with a map of the Trail Towns, letting tourists know that it’s a great way to see the small towns throughout our wonderful state. That’s what they find when they come to Everglades City, and they are excited to learn about the opportunities to see more of Old Florida.

Here’s more about the Everglades City Welcome Center: Everglades Local volunteers greet tourists from around the world and offer their expertise of the area to guide visitors to the various boat tours, museums, hiking, biking, and paddling opportunities. Maps and brochures are also available.

The center is operated by the Everglades Society for Historic Preservation which celebrates and preserves the unique cultural, historical, and ecological heritage of the area. Local arts and crafts are displayed and for sale in the center which is currently housed in the Glades Building at 207 W. Broadway, across the street from the historic Bank of Everglades which is being rehabilitated as the new Welcome Center and Trail Town Headquarters.

The Welcome Center is open seven days a week from 9:30 a.m. to 4 p.m. For more information, call (239) 719-0020

     To learn more about the program, visit the Trail Town website.