Crestview, FL Hiking Trails and Maps

99 Reviews

Looking for the best Hiking trails around Crestview?

Find the top rated hiking trails in Crestview, whether you're looking for an easy short hiking trail or a long hiking trail, you'll find what you're looking for. Click on a hiking trail below to find trail descriptions, trail maps, photos, and reviews.

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Activities
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7 Results
Activities
Length
Surfaces
Type

Blackwater Heritage State Trail

9.6 mi
State: FL
Asphalt

Gulf Breeze Parkway Trail

3 mi
State: FL
Asphalt

Navarre Beach Bike Path

3.6 mi
State: FL
Asphalt

Old Brick Road Trail

5.4 mi
State: FL
Brick, Concrete

Pensacola Beach Trail

9.1 mi
State: FL
Asphalt

Timpoochee Trail

18.5 mi
State: FL
Asphalt
Trail Image Trail Name States Length Surface Rating
In Milton, just northeast of Pensacola, the nearly 10-mile Blackwater Heritage State Trail is the rewarding result of a partnership between Florida's Departments of Transportation and Environmental...
FL 9.6 mi Asphalt
A sidepath trail that follows a stretch of its namesake roadway south of Pensacola, the Gulf Breeze Parkway Trail offers a useful transportation route for cyclists and pedestrians looking to navigate...
FL 3 mi Asphalt
Crystal white beaches and Florida-blue water are all par for the course at Navarre Beach. The Bike Path is a low-stress way to travel along Gulf Boulevard/ CR 399 to through the residential part of...
FL 3.6 mi Asphalt
Following the route of an old red-brick highway constructed in 1921, the Old Brick Road Trail provides over five miles of trail for cyclists and pedestrians on the eastern outskirts of Milton,...
FL 5.4 mi Brick, Concrete
This is a multi-use trail that runs along Via de Luna Drive and Fort Pickens Road in Pensacola Beach, Florida. It mostly runs along the two roads but does offer some great ocean views along the way -...
FL 9.1 mi Asphalt
Closure Notice: Highway 30A is undergoing construction in Deer Lake State Park, as the road crosses Deer Lake. This construction will impact the Timpoochee Trail along MM 13-14. Overview The...
FL 18.5 mi Asphalt
The L&N Railroad Deport Walking Trail in Geneva, Alabama, is a 0.5-mile trail that follows a short segment of the abandoned right-of-way of the L&N Railroad (Louisville & Nashville). This flat,...
AL 0.6 mi Asphalt

Recent Trail Reviews

Navarre Beach Bike Path

Loved this ride-- rode it in late Feb, 70° and very little traffic through the national seashore portion. Loved the pristine dunes and having the ocean on one side and Santa Rosa sound on the other. Plenty of places to stop and rest or have a picnic.

February, 2024 by jsull2525

Loved this ride-- rode it in late Feb, 70° and very little traffic through the national seashore portion. Loved the pristine dunes and having the ocean on one side and Santa Rosa sound on the other. Plenty of places to stop and rest or have a picnic.

Timpoochee Trail

Beach Towns Trail

February, 2024 by jallen1804

The trail is narrow & crosses the road several times as it passes through beach towns on the Gulf of Mexico. The scenery is pretty decent. I rode it on a weekday in February & it was pretty busy. It's worth the time if you're in the area.

Timpoochee Trail

Trail Closed 2/02/2024

February, 2024 by lammersbw

Left Rosemary Beach and headed west on Friday, February 2nd, 2024. Road and trail was completely closed around Mile 13..no way to detour…planning on 30 miles plus with lunch in Seaside..had to turn back. Deer Lake Park was worth the visit.

Accordion

Timpoochee Trail

A must do trail if you visit anywhere on the 30A!

December, 2023 by bikrgurl

The trail is awesome with several bridges over more than 11 lakes, meandering through several beach towns and neighborhoods. There’s public beach access along the way as well as many restaurants, coffee shops, bike shops and other retail. At mile marker 5 from the east of Inlet Beach, the trail/road over Deer Lake is all torn up. I was able to walk around the construction because no one was around on Christmas Eve Day when I did the ride, but normally you probably wouldn’t be able to. I was able to complete the entire trail from Shades Bar and Grill on the east trailhead to Topsail Hill State Park on the west end. Loved the adventure. Hybrid bike on all paved trails; 5 hours to complete; 40 miles out and back; 11mph; 650 ft elevation. (flat)

Pensacola Beach Trail

Great ride

August, 2023 by avwarcpo

Sure it’s a bit busy and “townie” in the middle but it’s a charming, well maintained and absolutely beautiful ride. The sand dunes and birds with the ocean sounds in the background. We thoroughly enjoyed this trail.

Blackwater Heritage State Trail

Nice Surprise

May, 2023 by eguydjr

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.

Blackwater Heritage State Trail

Great way to spend a day of our Pensacola vacation

April, 2023 by kahlershare

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!

Timpoochee Trail

Great for a vacation spin

February, 2023 by joseph.klarr

I was a little worried about taking my road bike on this trail based on some reviews, but it was actually pretty great! It's not the same as riding on a wide shoulder on sparse roads, but the foot/slower bike traffic isn't bad, and there's plenty of room to pass. the path is pretty well maintained. the biggest issue is a few points where you have to cross the road and switch sides. Still, I averaged about 16.5 mph and could have gone a bit faster if I wanted to. You're not going to get race training in here, but if you just want to get the legs moving, this is a great option.

Navarre Beach Bike Path

Not a 4 mile trail

January, 2023 by jmk355

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.

Blackwater Heritage State Trail

well maintained trail

January, 2023 by kevievn

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.

Navarre Beach Bike Path

Great pedestrian and cycling trail

January, 2023 by dustonm

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.

Timpoochee Trail

NOT a road bike trail

December, 2022 by kymbrell

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.

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Accordion

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