Crestview, FL Trails and Maps

70 Reviews

Looking for the best trails around Crestview?

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.

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Activities
Length
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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

19 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
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
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
The Timpoochee Trail traces the Gulf of Mexico shoreline and Scenic Highway 30-A as it travels through beachside communities and state forest lands between Dune Allen and Rosemary Beach. Trail-goers...
FL 19 mi Asphalt

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Trails by activity

Old Brick Road Trail

FL - 5.4 miles

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,...

Pensacola Beach Trail

FL - 9.1 miles

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 -...

Blackwater Heritage State Trail

FL - 9.6 miles

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...

Navarre Beach Bike Path

FL - 3.6 miles

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...

Accordion

Gulf Breeze Parkway Trail

FL - 3 miles

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...

Timpoochee Trail

FL - 19 miles

The Timpoochee Trail traces the Gulf of Mexico shoreline and Scenic Highway 30-A as it travels through beachside communities and state forest lands between Dune Allen and Rosemary Beach. Trail-goers...

L&N Railroad Depot Walking Trail (Geneva)

AL - 0.6 miles

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,...

Timpoochee Trail

FL - 19 miles

The Timpoochee Trail traces the Gulf of Mexico shoreline and Scenic Highway 30-A as it travels through beachside communities and state forest lands between Dune Allen and Rosemary Beach. Trail-goers...

Navarre Beach Bike Path

FL - 3.6 miles

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...

Gulf Breeze Parkway Trail

FL - 3 miles

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...

L&N Railroad Depot Walking Trail (Geneva)

AL - 0.6 miles

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,...

Accordion

Old Brick Road Trail

FL - 5.4 miles

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,...

Blackwater Heritage State Trail

FL - 9.6 miles

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...

L&N Railroad Depot Walking Trail (Geneva)

AL - 0.6 miles

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,...

Blackwater Heritage State Trail

FL - 9.6 miles

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...

Timpoochee Trail

FL - 19 miles

The Timpoochee Trail traces the Gulf of Mexico shoreline and Scenic Highway 30-A as it travels through beachside communities and state forest lands between Dune Allen and Rosemary Beach. Trail-goers...

Gulf Breeze Parkway Trail

FL - 3 miles

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...

Accordion

Pensacola Beach Trail

FL - 9.1 miles

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 -...

Old Brick Road Trail

FL - 5.4 miles

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,...

Navarre Beach Bike Path

FL - 3.6 miles

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...

Recent Trail Reviews

Blackwater Heritage State Trail

Awesome trail for all levels of cyclists. Trail is well maintained and the majority of local motorists yield for crossing cyclists. Great countryside scenery for most of the ride. Mostly flat terrain in very beginner friendly.

February, 2021 by raydallen86

Awesome trail for all levels of cyclists. Trail is well maintained and the majority of local motorists yield for crossing cyclists. Great countryside scenery for most of the ride. Mostly flat terrain in very beginner friendly.

Blackwater Heritage State Trail

awesome trail

January, 2021 by 2nu9w863u5

Great ride with nice country views most of the way.

Pensacola Beach Trail

very beautiful ride with visible bike path “most” of the way.

January, 2021 by 2nu9w863u5

If you park near the “Pensacola Beach Ball Tower” and start your ride from there all the way through Fort Dickens it comes to about 20 miles. Beautiful ride with a safe bike lane most of the way. The old fort is not much to look at, but it is still a great ride. It is costly to go into the park via bicycle. I think it was $15 unless your military like me and then it is free.

Accordion

Blackwater Heritage State Trail

Illinoisans!

January, 2021 by katrichar3636

Nice trail....well maintained. Saw turtles and birds. Benches and restrooms! Restrooms clean with hand sanitizer!!!!

Blackwater Heritage State Trail

black water state trail

January, 2021 by mleblanc4_tl

Nice trail. Multiple access points with parking. Connects to military trail that dead ends at NAS Whiting field

Timpoochee Trail

Great trail, busy beautiful!!

October, 2020 by marysconnor

Great trail, busy beautiful!!

Old Brick Road Trail

Definitely worth a quick visit for photos. Compared to other brick roads I've traveled, it's relatively smooth. I run 23s.

October, 2020 by blkreatta

Definitely worth a quick visit for photos. Compared to other brick roads I've traveled, it's relatively smooth. I run 23s.

Timpoochee Trail

A nice ride

September, 2020 by swgross

We rode the trail on a late September morning and had a great time. We parked on a public beach lot and rode east to Rosemary beach for a total of about 30 miles round trip. The trail is well kept and we had shade for about half of the ride (there was less as the sun went overhead). For the most part, people we encountered on the trail were friendly and courteous but it did get a little congested around Seaside. It’s a nice, relaxing ride on a smooth asphalt trail.

Blackwater Heritage State Trail

Nice ride

August, 2020 by curls3510

The most difficult part of the ride is in the town with crossing streets, but only one is really busy. Majority of the ride toward the naval base is quiet. About half of the trail has shade. We drove an hour from AL to ride this trail and we are looking forward to riding again

Blackwater Heritage State Trail

Nice trail me and wife had a great time

July, 2020 by jeffpitterman

Nice trail me and wife had a great time

Timpoochee Trail

Great Trail

June, 2020 by dpettibone

I live in the area. During tourist season it can get quite crowded (as do the highways and grocery stores). During off season it is a pleasant ride. No walkers 3 abreast and not paying attention to your bell. I’ve now just started to shout bike on the left and that helps. The areas this trail follows has a lot of beach rentals and the little towns are just crawling with people. Views are pretty but there are other trailsduring peak season.

Blackwater Heritage State Trail

Nice trail

April, 2020 by mardis5620

Rode this trail Dec 2019. Nice weather, pretty trail that meanders thru the backside of neighborhoods and countryside. Well maintained.

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