Longleaf Greenway Trail

The Path Less Traveled

Off–road biking + coastal Florida.
Yep, it’s a thing. Introducing the Longleaf Greenway Trail.

2020 was a year that defied description. It was a year of learning through hard lessons. It was a year that required us to adapt and change continuously. The idea of work fundamentally changed for so many of us, including myself. I learned how to meet with workmates safely, which was almost exclusively online. I learned to mute myself when not speaking. I learned to unmute myself before speaking.

And yet, some elements of everyday life remained unchanged. One of those elements lay just beyond the doorstep—off in the woods, along the beach, out on the water. The presence had been there all along in my previous pre-pandemic life, back when I was too busy rushing from one place to another. Suddenly, amid work-from-home orders and stay-at-home mandates, I had the time to wander off, to explore the vast, wide-open spaces around me. One of those places was the Longleaf Greenway Trail in Point Washington State Park.


The 30A corridor boasts idyllic beach towns, all of them strung together by the namesake highway that runs along the Gulf Coast. They’re also connected by the Timpoochee Trail, a paved 19-mile path that invites runners, bikers, walkers—even the occasional hoverboarder.

However, unbeknownst to man, there’s another byway: A 14.2-mile dirt-and-sand single-track with shady overhanging longleaf pines—the Longleaf Greenway Trail. Here you can witness mist lifting off the forest floor in the early morning. You can take in unpolluted views of the stars peeking through treetops on a cloudless night. And you’d never know that you’re less than a mile from the beach.

The western Longleaf Greenway Trailhead begins in Blue Mountain Beach and terminates at the eastern trailhead on South County Highway 395. The trail itself becomes muddy after a heavy rain—and yet it’s still worth the trouble if you’re undaunted by the prospect of tromping through a few brief stretches of ankle-deep slop. County Highway 83 and 283 serve as “bail-out” points between the trailheads, dividing the trail roughly into thirds. If you are not up for riding or hiking the entire trail, turn south on the paved bike paths running alongside either highway. Both lead back to 30A and the Timpoochee Trail.


The western trailhead is located just off of Sea Pond Road in Blue Mountain Beach. There’s a restroom and a picnic pavilion on site, and usually plenty of parking. Once on the trail, you’ll see small orange-and-black markers posted on the pines that indicate the route. The sand trail is occasionally soft, requiring that you dismount and walk a few yards. Generally, however, it’s firm enough to ride—and wending your way through endless tight turns through the forest is utterly exhilarating.

Once you reach Highway 83, you’re presented with the option to explore Blue Mountain Beach, just 0.6 miles south on the paved bike path. Start with dessert at Blue Mountain Creamery, where homemade ice cream, frozen yogurt, and sorbet are served. If in more of a shake, float, donut, or coffee mood, head next door to the Shake Shop. Blue Mable Smokehouse & Provisions is located just over the hill, offering outdoor dining with everything from smoked wings and juicy burgers to shrimp and grits. For the healthier crowd, stop by For the Health of It. It’s just across the street, serving juices, smoothies, and various organic produce— and right next door to Big Daddy’s, one of the finest bicycle shops in all of Florida.


The Longleaf Greenway Trail offers more winding paths through the pines. You’ll cross a firebreak road before returning to a single-track path that incorporates small wooden bridges arching over slow-moving creeks. The three-mile trek from Highway 83 to Highway 283 is the longest uninterrupted stretch of the trail, and the reward for completing it is awesome. Once you reach Highway 283, you can take the paved bike path to Grayton Beach, where you’ll find a delectable tartine and lavender latte from Black Bear Bakery and the Grayton Brew Pub serving up cold ones. And this is just the beginning of a multitude of nearby dining options.


The final 2.1-mile leg winds through pines and palmettos. The finish line, of course, is the Highway 395 Trailhead, which doubles as a small park with restrooms and picnic tables. It’s also a jump-off point to explore WaterColor or Seagrove Beach just a couple of miles south on the Highway 395 bike path. Fill up on a shrimp po’boy at Village Seagrove Market near the corner of Highway 395 and 30A, or sink your teeth into a large slice of pizza at Pizza by the Sea. By now, you deserve it.


The Longleaf Greenway Trail is a place to find solace in nature—and it’s right here in my own backyard. In a strange way, it serves as a benchmark between the past year and the present, a lens to view the rearranged landscape around me, to locate myself in a world that has changed in countless ways over the past two years. Like 2020, the trail is both close to home and far from the known.


The Longleaf Greenway Trail is open 365 days a year. As of this writing, the cost to park at the Western Trailhead is $2.00 per person per day. Children six and under are free. While the trail is mostly flat, I recommend wearing closed-toed shoes. Also, bring water, sunscreen, a headlamp, a mask or buff, and a smartphone in the event you get a little disoriented. If riding a bike, always wear a helmet. Dogs are permitted on the trail but must remain leased at all times. Lastly, this is a multi- use trail. Please respect all those you pass.

And, as always, leave no trace.