Explore the best rated trails in Crestview, FL. Whether you're looking for an easy walking trail or a bike trail like the Old Brick Road Trail and Pensacola Beach Trail. With more than 7 trails covering 50 miles you're bound to find a perfect trail for you. Click on any trail below to find trail descriptions, trail maps, photos, and reviews.
I've done this trail 3x now. Last year just out to the Base, & this year 2 times with the wife. Great ride, the last leg before the base is the only trying hill & it was a Very windy day, but that made for a Zoom back to town Had lunch at Cosse's when we finished.
We had planned to ride the Pensacola beach trail, but changed our minds after seeing the beach crowds we would have to navigate around. Instead, we drove out to Milton and rode the Blackwater Heritage State Trail. So glad we did! We entered the trail at the visitor center in Milton and rode to the naval air station and back twice, giving us about 32 miles total. The trail was very well maintained, with occasional benches and several restrooms well spaced all along the length of the trail. Before getting out of Milton (perhaps the first mile after the visitor center), we had to cross several small-town roads, after which the crossings were less frequent but a bit more challenging. Nothing we couldn't handle, though.
The countryside we passed through along the ride was mostly pretty and interesting. When we got close to the air station, we felt like we were vaguely surveilled by a helicopter, but no one approached or bothered us. Overall, a great ride that we would gladly do again!
The only 20+ mile trail in the area. Cobble together this trail and the Pensacola Beach trail and the ample bike lanes in between and toward Ft Pickens and you get a really fun and scenic ride. Pay attention to wind direction and speeds.
January 2023 We started at the library and because we didn't want to bike through town. The parking is limited. Further up there is a large lot which may be better. The trail is asphalt and level. No roots through the pavement and very little debris. Wonderful trail.
Great trail with access and parking near the Tom Thumb convenience store. The trail runs east for a short distance, and then West towards the Gulf Shores national seashore. At this point it is connected, through a bike lane that runs the length of the national seashore. Traffic is slow, so it is a very scenic and enjoyable ride. Out and back from the convenience store is approximately an 18 to 20 mile ride. Additional miles can be added on by taking the trail that connects on the west end of the seashore into Pensacola and all out to the Fort Pickens national park.
This is NOT a rail trail or anything similar just to manage expectations. This is a nice family cruiser bike “path” or nice for walkers and runners. As a road cyclist, I was super excited about a paved “trail”. SMH. It is best for a road cyclist to just prepare to ride on a very narrow road most of the way sharing the road with vehicles.
BEWARE !! in Seagrove Beach, the red light at the intersection of 30A and S.Co. Hwy 395--we were on the bike trail, we had a green light , going west, and nearly were run over by pickup trucks and cars turning right. I assumed we had the right of way, but the trucks and cars paid us no attention, just zoomed around the corner. Very disturbing !!
Love this ride that takes you through a canopy of trees to open areas filled with wild flowers. You can extend the ride by heading up Copter Road that circles around NAS Whiting Field and through cotton fields.
Did the entire trail along with picking up all but just a few geocaches along the trail. Nice riding, just a few street crossings and different scenery along the way.
Parked at the most southern trailhead. Bathroom facilities were clean and stocked with soap and paper towels. Quite a few roads to cross in the beginning. While not difficult it’s aggravating. Afterwards trail cruises on. Nice people on trail and I felt safe. Would ride again.
Five stars? Really? Okay, for the walkers and joggers in town, I can see five stars. For us folks on bikes, not so much,
On an absolutely perfect spring morning in late March, we started from the west trailhead where we were greeted by pristine white sand and a beautiful great blue heron. After that, for the next seven full miles, it was all downhill (figuratively, not literally). The first seven miles is essentially a poorly maintained asphalt sidewalk which crosses a multitude of hotel, restaurant, resort, and rental property driveways. In addition, there are an extreme amount of streets to cross. Again, fine and dandy for the huge numbers of pedestrians on Spring Break on the Redneck Riviera, not so great as you pedal along on high alert for two tons of steel possibly veering your way.
The Fort Pickens Road parking lot at the western trailhead has restrooms and beach access to the amazing white sand and rolling breakers, but once on the official Pensacola Beach Trail through town there's very little to see but hotels and businesses. After a few miles you reach the Highway 399 portion the trail parallels, but once you finally leave the business district it's then miles of homes and still no gulf views.
Finally, after passing the Portofino Resort, no more driveways or cross streets, nothing but white sand dunes on both sides of the trail with views of Santa Rosa Sound and occasional glimpses of the gulf. Unfortunately, the trail quality doesn't get any better for us bike riders, but at least your head doesn't have to be on a swivel to avoid being run over.
The payoff is reaching the eastern terminus of the trail. Be sure to cross the highway and soak in the natural beauty and tranquility. The beach was pretty much deserted since there are no homes, resorts, or parking lots at that spot. We had the beach all to ourselves! It was just us, the immaculate white sand, gentle waves, and yet another great blue heron!
For bicyclists, seven-ninths of the trail in my opinion is below average; two-ninths of it is pretty cool!
For walkers and people getting around town, 100% great.
SOME FOOD FOR THOUGHT: On the way back to town, we turned onto Avenida 22 toward Santa Rosa Sound to avoid the hustle and bustle of Highway 399. We enjoyed marvelous views of the sound and amazing homes on quiet residential streets for a mile or two before being forced back onto the trail and the commotion along Highway 399.
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