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Miami to Orlando road trip: Quaint towns, trails and hills along US 27

Many will be surprised to find a Florida without beaches or traffic jams. If it’s a taste of Old Florida you crave, this is for you.

This region is Florida off the beaten track and yet it’s only two or three hours from the major population centers in South Florida, Orlando and Tampa Bay.

Locations included in this Miami to Orlando road trip

What’s particularly special about this region is the Lakes Wales Ridge, a 150-mile-long stretch of higher ground, between Lake Placid and Clermont. Several million years ago, when most of Florida was underwater, the ridge was an island where plants and animals continued to evolve in isolation. (Someday, if sea levels rise, it again will be the part of Florida that pokes out of the sea.)

If you start from the south, you begin near Lake Okeechobee, and then drive on to Lake Placid, Sebring, Avon Park, Lake Wales ending in Winter Garden, a suburb of Orlando. We include two optional sidetrips.

miami to orlando 2023 6 map for US 27 Road Trip Miami to Orlando road trip: Quaint towns, trails and hills along US 27
Road trip from Miami to Orlando through Old Florida:

Road trip from Miami to Orlando through Old Florida:

  • Day 1: Fisheating Creek
  • Day 2: Historic small towns
  • Sidetrip: Cracker Trail
  • Day 3 and 4: Lake Wales
  • Sidetrip: Lakeland
  • Day 5: Winter Garden

Length of the road trip from Miami to Orlando

You can do this getaway in two to three days, but if you immerse yourself in one of these state parks, spend a half a day hiking, bring your bicycle or kayak for stops along the way, or if you’re a camper who savors just spending times in the woods, you could easily enjoy five or six days on the trip.

Our road trip itinerary is five days, but you can condense it by skipping things of your choice. For example, skip Fisheating Creek if the water level is low or you’re not a paddler. Or, in the Lake Wales area, choose either Bok Tower OR Lake Kissimmee State Park and visit it for only a day.

From south to north, this route begins in the middle of the state west of Lake Okeechobee. US 27, the major artery up the spine of the state, can be reached easily from the either coast.

Our itinerary emphasizes places to kayak, bike and hike, and this region offers excellence possibilities. We also suggest some good camping locations. Without beaches or springs, this trip will be better in cooler weather.

Fisheating Creek is spectacularly scenic, with every stroke of the 8-mile kayak trail bringing a photo-worthy scene and the sounds of wildlife. It's a great way to spend the first day of your road trip from Miami to Orlando. (Photo: Bonnie Gross)
Fisheating Creek is spectacularly scenic, with every stroke of the 8-mile kayak trail bringing a photo-worthy scene and the sounds of wildlife. It’s a great way to spend the first day of your road trip from Miami to Orlando. (Photo: Bonnie Gross)

Day 1: Start with a kayak trip on Fisheating Creek

Fisheating Creek, located due west of Lake O near Palmdale, is one of the most beautiful and wildest rivers in Florida. There are great facilities at the Fisheating Creek Outpost, a live-oak-shaded campground and boat ramp right off U.S. 27. You can arrange a one-way eight-mile kayak trip with livery service if the water is high enough (usually from summer through November to January) or take an out-and-back with a rental kayak if water levels are low. (Here’s where to check.) Here’s a complete guide to Fisheating Creek. If you’re a camper, consider this for your first night.

Where to spend the night: If you’re not camping, stay in Lake Placid, where we list several alternatives.

The next section of US 27 is a cluster of four charming Old Florida towns: Lake Placid, Sebring, Avon Park and Lake Wales, all within 50 miles. You could base yourself in any of them. We suggest you spend one night in the southern end (Lake Placid to Sebring) and two nights in the northern end (Lake Wales) in order to spend time in the various parks and attractions along the way.

lake placid sebring clown school silly dilly
Toby’s Clown School and Museum in Lake Placid is one of the unusual attractions in Lake Placid. The mural is one of 50 around town. (Photo by Bob Rountree)

Day 2: Explore historic towns and state parks

Lake Placid is 27 miles up the road from Fisheating Creek, and it once won the title of “America’s Most Interesting Town.” It’s a fun place to explore because it is full of murals (there are more than 50.) Lake Placid highlights include Toby’s Clown School and the American Clown Museum and there are atmospheric places to eat and drink too.

Have lunch at Morty and Edna’s Craft Kitchen.  This cute cafe is in the heart of Lake Placid in the Journal Plaza, where the town’s local newspaper was once published. (Try the Notorious BLT, consisting of candied bacon, avocado, fresh tomato and lettuce on sourdough breae.)

In the evening, stop next door at  the Wet Dogs Brewing Company, which serves their craft beer plus locally crafted sodas and hard seltzers. 

Then have dinner at Cowpokes Watering Hole, about 10 miles north of Lake Placid. It serves premium steaks and fresh seafood in its ranch-themed dining room or outside in its large tiki bar. Cowpokes is a local landmark that celebrates the region’s Florida Cracker heritage.

Lake Placid is where 98 percent of the world’s supply of the colorful tropical caladium plant is grown. There are vast fields of bright colors in the summer as well as a Caladium Festival in July.

Here’s a Florida Rambler guide to visiting Lake Placid.

Ancient oak at Highland Hammocks State Park, a stop we recommend on this Miami to Orlando road trip. (Photo: Bonnie Gross)
Ancient oak at Highland Hammocks State Park, a stop we recommend on this Miami to Orlando road trip. (Photo: Bonnie Gross)

Highland Hammocks State Park, a few miles north of Lake Placid, is one of Florida’s four original state parks and worth several hours of your time. It preserves many old-growth live oak trees, which over the years acquire huge, warty, personality-filled trunks and twisty branches.

The park has many short hikes, including the Wild Orange Grove trail, site of a pioneer’s grove, now a forest in which orange trees are interspersed, and an elevated boardwalk through an old-growth cypress swamp. There is also a fascinating small museum devoted to the Civilian Conservation Corps, which built many of the park’s original buildings. If you’re a camper, Highlands Hammocks is a great place to book a space. Here’s a Florida Rambler guide to Highlands Hammock State Park.

Sidetrip: The Cracker Tail

Before you reach Sebring, you cross US 98, which is called the Old Cracker Trail. Each year, during the last full week of February, dozens of people on horseback and covered wagons take the Cracker Trail in a re-creation of the life of Florida’s cow hunters, pioneers of the late 1800s. The ride takes nine days to cross 140 miles across Florida from Bradenton to Fort Pierce. You can drive a bit of the Cracker Trail and we recommend a few stops along the way in our guide to the Old Cracker Trail.

Sebring, the next town heading north, is best known for Sebring International Raceway, home of the renowned “12 Hours of Sebring Grand Prix of Endurance,” America’s oldest racing event and prelude to the 24 Hours of LeMans. But this historic town has more to offer, including a beautiful drive around Lake Jackson at the center of town, where there is a fishing pier that is perfect for a sunset stroll.  

Kayaking Arbuckle Creek, near Sebring and Avon Park: You’ll have to bring your own kayak for this little-known gem. Arbuckle Creek is a gorgeous wild river through an ancient cypress forest. The river forms the border of the Avon Park Air Force Range, so it escaped development and remains quiet and pristine. The river flows into Lake Arbuckle, on whose shores there are campsites and a state forest. Florida Rambler on kayaking Arbuckle Creek.

In the historic Avon Park downtown, the Hotel Jacaranda opened in 1926 and never closed. It's a budget spot to stay on this road trip from Miami to Orlando. (Photo: Bonnie Gross)
In the historic Avon Park downtown, the Hotel Jacaranda opened in 1926 and never closed. It’s a budget spot to stay on this road trip from Miami to Orlando. (Photo: Bonnie Gross)

Avon Park, 10 miles north of Sebring, has a historic downtown where the Avon Park Depot Museum, with a restored 1948 railroad dining car, is located right off Main Street. Also in Avon Park, visitors gather on rocking chairs and enjoy the legendary orange ice cream at an old fashioned general store and farmer’s market, Maxwell Groves Country Store. The place has been there for 80 years, and it looks it. Another historic site downtown is the Hotel Jacaranda, listed below.

Where to spend the night in Lake Placid, Sebring or Avon Park

  • Lake Grassy Inn and Suites, 1865 US-27 S, Lake Placid, FL 33852. Phone: (863) 465-9200. Lakefront suites. Check prices on
  • Holiday Inn Express and Suites, 608 S Lakeview Rd, Lake Placid, FL, 33852. Phone: (863) 465-9916. Check latest rates on
  • Ramada by Windham, 2165 US-27, Lake Placid, FL 33852. Phone: (863) 840-9907. Check latest discount rates on
  • Inn on the Lakes, 3101 Golfview Road, Sebring, FL 33870. Phone: (863) 471-9400. Locally owned hotel with a good restaurant and bar, Chicanes.
  • Avon Park Hotel Jacaranda, 19 E. Main St., Avon Park. Phone: (863) 453-2211. This the place for people who love historic hotels or for budget travelers. The expansive lobby is a step back in time, with paintings by the Florida Highwaymen, an old piano that is played daily during winter season and a library with an antique writing desk. Rooms are inexpensive, but plumbing is old, so this is not for everybody. Here’s a Florida Rambler story on the Hotel Jacaranda.
miami to orlando bok reflection pool 3576 Miami to Orlando road trip: Quaint towns, trails and hills along US 27
The Bok Tower and Gardens Reflection Pool captures the 205-foot-tall carillon standing majestically at one end. It’s a must-see on US 27 from Miami to Orlando. (Photo: Deborah Hartz-Seeley)

Day 3 and 4: Explore a historic Florida garden atop a “mountain” and a night in charming Lake Wales

Bok Tower, just a few miles outside downtown Lake Wales, is one of the top botanical gardens in Florida and it occupies a unique location – Mount Iron, which at 298 feet, is one of the highest spots in peninsular Florida. It’s part of a ridge that is millions of years old.

At the 250-acre Bok Tower Gardens in Lake Wales, you can wander through manicured greenery, visit a historic home, let your kids explore a garden just for them, enjoy a pleasant lunch at a café and wander trails through disappearing habitats. Here too you’ll see lush azaleas, camellias and magnolias in season. From just about any place in the garden, you can hear the music of a 60-bell carillon that is played regularly. It’s easy to spend several hours here. Here’s a guide to Bok Towers Gardens from Florida Rambler.

The small town of Lake Wales does have a lake at its center and you can drive around the lake hugging the shoreline to view older homes. You also can walk/bike on a lighted and paved path that covers about 2.5 miles or about three quarters of the lake’s circumference.

Downtown Lakes Wales has 11 historic buildings, some nicely preserved and refurbished. They are easy to visit via the downloadable Walk Lake Wales city map that is the work of the Lake Wales History Museum. The tour also is available on the free Florida Stories app available in iTunes and Google Play. The app is GPS enabled and provides narration and photos that cover each tour stop.

Here’s a guide from Florida Rambler on things to do in Lake Wales.

Lake Kissimmee State Park cow camp
At Lake Kissimmee State Park, historic re-enactors make an 1870s cow camp come alive, including with Cracker cattle in residence. (Photo: David Blasco)

Lake Kissimmee State Park, a half hour east of Lake Wales, is a perfect place to spend a day hiking, kayaking, spotting wildlife and, if you’re there on the weekend, visiting a re-enactment of a “cow camp” complete with Cracker cattle and cow hunters. (That’s what cowboys were called in Old Florida.) Here’s a Florida Rambler guide to Lake Kissimmee State Park. If you’re a camper, this is a great place to book a site.

Tiger Creek Preserve, 20 minutes east of Lake Wales, is the ideal place for a hike to appreciate the unique landscape of the Lake Wales Ridge. The Nature Conservancy preserves it because it holds “one of the highest concentrations of threatened and endangered plants and animals in the country. “ Plants grow here that are not found anywhere else. It has 10 miles of trails, but no restrooms, no water and no picnic tables. Here’s a Florida Rambler guide to Tiger Creek Preserve.

Traveling with kids? Legoland is six miles off US 27 just north of Lake Wales. The hands-on theme park has 60 rides, shows and attractions, for families with children 2 to 12. Back in the day, this theme park was Cypress Gardens and the lakes and gardens are still beautifully landscaped.

Where to eat in Lake Wales area

While visiting Bok Tower Gardens, the most convenient place to eat breakfast or lunch is the Blue Palmetto Café This order-at-the-counter restaurant offers indoor and outdoor dining adjacent to the Visitor Center. (You have to pay the garden admission fee to access the restaurant.)

For dinner, consider Melanie’s Seafood Company, in historic downtown Lake Wales. The small storefront offers fresh food, friendly table service and fair prices. You can visit on Facebook.

Where to stay in Lake Wales

Holiday Inn Express Lake Wales N-Winter Haven, 2953 Ridge Way, Lake Wales, FL 33859. (863) 949-4800

Hampton Inn & Suites Lake Wales, 22900 US Hwy 27, Lake Wales, FL 33859. (863) 734-3000

Westgate River Ranch Resort and Rodeo, 3200 River Ranch Blvd., River Ranch, FL 33867. (863) 692-1321. For something more rustic, head about a half hour out of town to River Ranch, which has a variety of accommodations including glamping, luxe teepees and comfy Conestoga wagons. This is a resort that is a destination unto itself, with line dancing, horseback riding and Saturday night rodeos.

Camp Mack, 14900 Camp Mack Road, Lake Wales, FL 33898. (863) 696-1108.
Across the street from the entrance to Lake Kissimmee State Park, there’s a big RV camp that includes cabins and a fishing-themed motel.  From the property, you can access the water in your bass boat or kayak; air boat tours also are available.

The bridge over Big Creek at Lake Louisa State Park in Clermont. (Photo: Bonnie Gross)
The bridge over Big Creek at Lake Louisa State Park in Clermont. (Photo: Bonnie Gross)

Day 5: Bicycling, trails and historic Winter Garden

After staying two nights in the Lake Wales area, you head northeast and end in Winter Garden, a historic town now considered an Orlando suburb. This part of the road trip is ideal for bicyclists, in that there are two excellent paved rail trails here.

If you have the time, we suggest you add a day to your road trip and make a side trip to Lakeland, which is decribed below.

As you head north on US 27, stop at Lake Louisa State Park, where you’ll find a landscape of rolling sand hills, lush cypress swamps and miles of pine forests dotted with scenic lakes. There are 20 miles of trails and it’s a good place for bicycling too. If you’re a camper, this is a good place to book a night or two and we also highly recommend the state-park cabins at Lake Louisa, which have a two-night minimum. Here’s a Florida Rambler story on Lake Louisa State Park.

Bicyclists have another excellent option, the 29-mile Van Fleet Trail. This paved state bike trail goes through the Green Swamp, a vast watery wilderness west of Orlando. With few cross streets, this is one of the most rural and remote bike trails in the state. It’s just west of Lake Louisa. Here’s a Florida Rambler story about the Van Fleet Trail.

The West Orange Trail is one of Florida's best bike trails. It passes through charming Winter Garden and other small towns in Central Florida. (Photo: Bonnie Gross)
The West Orange Trail is one of Florida’s best bike trails. It passes through charming Winter Garden and other small towns in Central Florida. (Photo: Bonnie Gross)

Winter Garden, 15 miles northeast and your end-of-trip destination, has a quaint old-fashioned downtown full of restaurants, museums, fountains, bike shops, boutiques and all sorts of people on bicycles and foot. The West Orange Trail, a 22-mile bicycle trail, runs right down the middle of the main street. If you didn’t bring a bike, this is the place to ride: It’s easy to rent one here to ride on the trail.

There are many good choices for restaurants. Consider:

The Plant Street Market and Crooked Can Brewery. This lively food court in the walkable downtown is anchored by a craft brewery, Crooked Can Brewery, which wins raves for its indoor and outdoor seating. You can get a wide variety of food, from mac and cheese to barbecue to empanadas to hand-crafted popsicles.

Urban on Plant Kitchen & Bar, 132 W. Plant St., Winter Garden, FL 34787. (407) 614-2765

Chef’s Table in the Edgewater Hotel, 99 W Plant St., Winter Garden, FL 34787. (407) 230-4837

Where to stay in Winter Garden

Edgewater Hotel, 99 W. Plant St., Winter Garden, FL 34787. (407) 654-6921

The Historic Edgewater Hotel, built in 1924, is a beautifully preserved historic hotel with a bed-and-breakfast style and reasonable rates. The hotel’s first floor still has the original picturesque front desk, fireplace and skylight-lit lobby. The hotel’s guest rooms are on the second floor, where an inviting lobby filled with antiques also serves as the breakfast room. When you check in, a staff person takes you to the second floor on the 1926 hand-operated elevator.

Alternative lodging from all the major hotel chains is plentiful if you stay in the Orlando area, 20 minutes east, though you miss the small-town ambiance of Winter Garden’s downtown.

American eagle at Circle B Bar Reserve (Photo: David Blasco)
American eagle at Circle B Bar Reserve (Photo: David Blasco)

Sidetrip: Circle B Bar Reserve and Frank Lloyd Wright campus in Lakeland.

If you have the time and interest, this additional day offers two special destinations.

Circle B Bar Reserve, 25 miles northwest of Lake Wales, is one of the best places to spot wildlife in the region. Birders love it and if you haven’t see alligators by this time, it’s a great place for that. The scenic preserve is free and offers a variety of options for trails. Here’s a Florida Rambler story on Circle B Bar Reserve.

Lakeland and the Frank Lloyd Wright-designed campus of Florida Southern College. Florida Southern College in Lakeland has been named one of the 20 most beautiful college campuses in the country because it is unique: Nowhere else in the world has more buildings designed by Frank Lloyd Wright. Florida Southern College draws Frank Lloyd Wright fans from around the world. You can stroll the campus on a self-guided tour, but architecture buffs will want to book a guided tour. Here’s a Florida Rambler story on seeing the Frank Lloyd Wright buildings.

Frank Lloyd Wright Florida Southern College
Frank Lloyd Wright designed building make Florida Southern College a destination for architecture buffs from around the world. (Photo: Bonnie Gross)

Lakeland itself is worth exploring too. It has a traditional downtown with some good restaurants and shops at Main and Kentucky. That intersection is a block from lovely Mirror Lake with its historic Promenade, which makes a pleasant .65 mile walk around the lake. Along the walkway is Hollis Gardens, which has formal flower beds and fountains overlooking Mirror Lake.

There are many lakes in Lakeland, and you should watch for swans on them. They are all descendants of two royal swans bestowed on the city by Queen Elizabeth in 1954.

If you take this sidetrip, it’s an hour to Winter Garden or to Lake Louisa State Park, driving part of the way on I-4. Alternately, it’s 45 minutes west to Tampa.  

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