Looking for the best trails around Cumberland?

Explore the best rated trails in Cumberland, MD, whether you're looking for an easy walking trail or a bike trail like the Shuster Way Heritage Trail and Allegheny Highlands Trail . With more than 21 trails covering 4251 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.

Recent Trail Reviews

Chesapeake & Ohio Canal National Historical Park

Simply spectacular

June, 2025 by ethantabor

I just finished a two-day solo tour (Cumberland to Williamsport, Williamsport to DC) and had an incredible experience despite the rain and the tough going over a few stretches. I hear a lot of criticism about the C & O, particularly when compared to the GAP (which I have also done). I appreciate the contrast and hope that the C&O retains its historic character as a more rugged towpath (not a rail trail). That said, the conditions on the east side of Paw Paw and from White’s Ferry to DC were challenging (again, I like the changing surfaces). Highlights: wilderness character, Paw Paw Tunnel, sycamores between Harper’s Ferry and Antietam, Great Falls, Monocacy, Point of Rocks station and the towns.

Chesapeake & Ohio Canal National Historical Park

A Disappointment

June, 2025 by redebski

My son and I rode the C&O the first week of June '25 as part of a ride from Pittsburgh to Washington DC.

I am going to preface this review making it clear that it was an unusually wet Spring and significant damage has occurred due to flooding. Kudos to the efforts to repair the damage and keep the trail open. There were numerous detours off of the trail but it was open and passable. However, had I not taken this into consideration, and had not just completed the GAP as a comparison, I would have rated the trail 2 stars.

Here are my key issues rated from most, to least, significant:

1) The terminus of the trail in Georgetown is inaccessible due to construction. We rode 334 miles in 5 days to unceremoniously end our accomplishment carrying our bikes up a series of stairs, only to encounter detour signs that literally pointed in all four directions. After a half hour walking through urine-laden alleys searching for mile 0, a bicycle cop told us that we were as close as we could get. Our victory picture was taken next to a detour sign, each of us providing a middle-finger salute.

2) The trail surface through the Paw Paw tunnel can only be described as interconnecting pot holes filled with 6" of water. Had there not been other traffic in the tunnel, it may have been rideable. Just accept that you will get the opportunity to stretch your legs for a half-mile walk in the dark. Your shoes will eventually drain and dry by the time you arrive in DC.

3) For 15-20 miles south of the Paw Paw tunnel the trail is unmaintained. The riding surface is basically sunken truck tire tracks, separated by a hump of uncut weeds. The tracks themselves were devoid of any gravel which ensured that you were riding in either water or mud. The weeds on both sides of the trail had yet to be trimmed and had encroached into the tracks. The good news is that we were concentrating so hard on keeping our bikes upright in the slop, we didn't have time to think about the ticks. Anyone who has hiked the Adirondack high peaks knows exactly what I am describing.

4) Most of the trail repairs have been made with loose, coarse, crushed stone. I was fortunate to be riding a mountain bike with 2" tires at 60psi. My son was riding a gravel bike with 40mm tires which mean he was riding sideways much of the time. He ended up riding a combined total of 400 miles considering the lateral component of his travel.

5) Where washouts had yet to be filled with the previously mentioned stone, you have to cross crevices 6-8 inches deep. Not such a big problem if you were travelling slow enough to identify them before jamming your arms through your shoulders and ramming your saddle through the softer tissues of your rear end.

6) Having camped in Assateague for half my life, I thought that I knew aggressive mosquitoes. However, since the trail is totally devoid of any breeze, the stabbing critters locate you as soon as your bike comes to a halt. The good news is that we saved time taking breaks.

I will be posting a 5-star review for the GAP next. If you average the two scores together, the total trail experience was a 4. That still makes the ride from the 'Burgh to DC worthwhile. Just be prepared for the unexpected challenges.

Allegheny Highlands Trail

AHT

June, 2025 by davidspeno

We rode from Elkins out about 10 miles north towards Montrose and returned. The trail is in great condition. It was such a lovely day we regretted that we had not planned to ride further. Lovely farmland and plenty of shade. Good summer riding.

Accordion

Great Allegheny Passage

well maintained, pretty area

April, 2025 by astroman

PA-Cumberland 5/2023. Loved this trail with lots of places to camp, a winding and entertaining trail, views of the river, tunnels, small towns along the way. I particularly liked Frostburg and camped two nights. The switchbacks up to town aren't as miserable as some describe and the view is rewarding. The Toasted Goat in Hotel Gunter is an old hotel worth a walk around and a meal. Check out the basement holding cell and speakeasy.

Western Maryland Rail Trail

completely resurfaced 5 star

April, 2025 by aldo_desalvo

I rode this for a second time recently. The trail is in great shape. I will they would add the path through the tunnel. Extending the trail over the three bridges would make this the best in the area. Not sure if that is a plan. Hancock is a great town. Very remote in little orleans

Western Maryland Rail Trail

Wmrt 2025 all repaved

April, 2025 by loisslong

This is my favorite paved trail. All the bumps and roots are gone since the repaving project was completed in fall 2024. Hancock is the town at about the middle mileage. The western end is quiet through the woods. There are very few road crossings and it's pretty flat grade. Berkeley Springs WV is only 6 miles south of Hancock MD and that's a cute tourist town to visit. There's also a good bike store in Hancock.

Great American Rail-Trail

Warden to Lind

April, 2025 by howmarplus3

Ok section, kind of dull. Agriculture & cows. Found a bit of shade by a grain elevator for lunch. Several washouts filled with tumbleweeds as you get closer to Lind.

Allegheny Highlands Trail

Can put it all together!

January, 2025 by triathlon32

We rode the trail the week of Christmas (no snow). You CAN go all the way from Elkins, thru the construction, all the way to Hendricks. You can also ride the “proposed future trail” all the way to Thomas… and it’s beautiful in there! We were on gravel bikes and had zero issues. A mountain bike would work but not a road bike. Enjoy the entire trail if you have the fitness for it- it’s beautiful!

Shuster Way Heritage Trail

Not for road bikes.

December, 2024 by repacker

It's a nice walking trail, or if you're taking it to get to the MTB trails. But, if you have a road bike you should just take the road. It's a shame they couldn't have used crushed gravel so roadies could bypass the section of road past the Elks. As it is, it's worthless for road bikes.

Blair Brothers Trail

Nice extension when riding the Indian Creek Valley Trail

November, 2024 by vdeal

I rode this trail a week ago as part of a loop on the Indian Creek Valley Trail. The trail is easy to find and was relatively easy to ride on a gravel bike with 700 x 38 tires. There is a trail that splits off halfway but just stay straight and you'll be fine. There's really no issues with riding this unless you're trying to ride it on a skinny tire road bike. I enjoyed the trail.

Indian Creek Valley Bike Trail

Absolute joy of a trail near the GAP

November, 2024 by vdeal

I rode this trail on November 1st, a sunny but windy fall day. The leaves were off the trees mostly but were a beautiful carpet of color on the ground. I have ridden here before but never this late in the year and not for a few years. I started in the town of Indian Head as I always do. I first headed south and right away you do have to take a quick jog west on Indian Head Rd but the trail is easy to find. This section was in great shape and the tread was excellent. I rode south to the gate and seeing that people were continuing south on the unfinished section I rode on about .3 miles but there were some mud holes and the tires on my gravel bike weren't up to that task. Next time I'll bring the mountain bike and go further.

I went back to Indian Head and headed north. This was an extremely pleasant trail with what I can honestly say is the smoothest path (outside of pavement) I've ever ridden. It's actually smoother than some pavement. I flew along with only a few people on the trail until the town of Champion. Here you have to ride back Roaring Run Rd a short distance to regain the trail. From here on the trail, while still full width is only single track. For the most part though this single track is very smooth and quite rideable. At Jones Mills the trail ends in a short but steep climb up to Rt 31. As others have noted, there is no parking here.

I continued this ride by carefully crossing Rt 31 and riding down Rt 381 a short distance to the Blair Brothers Trail. This is a fairly easy 1.5 mile ride through the woods to a dirt road before turning around.

All-in-all, this is a great trail and likely to be much less crowded than the GAP. There is a diner in Indian Head (the Creekside Diner) if you need something to eat. I did not check it out though. Go and enjoy the trail.

Chesapeake & Ohio Canal National Historical Park

Rough with Rider-Beware Hazards

October, 2024 by morgan.paul511

I biked from Pittsburgh to DC (GAP and C&O trails combined) 9/8 thru 9/14/24. This review is for the C&O only. Weather – excellent. Scenery- beautiful. Accommodations – very good. Trail surfaces –highly variable from narrow dirt paths laced with muddy holes to relatively smooth, hardpacked dirt to loose gravel (better for a pickup truck than a bicycle!). From 10 miles south of Great Falls into DC the trail/road was especially rough. I was riding an Off-road bike with 40 MM wide tires and momentarily lost front tire stability in MANY spots due to loose gravel (especially on the sloped paths leading into & out of lock areas). My biggest safety concern were the numerous concrete bridges over creeks & culverts that had ZERO guard rails, warning signs or even yellow paint. The bridge widths were narrower than the trail requiring the biker to NOTICE and move more to the center for safety. If a biker went off the side of any of these bridges, I’d expect serious injuries or worse. The worst safety hazard was at Lock 38. Approaching the lock from the southwest side, the (main) trail leads right across the top of the lock wall- that is 3 to 4 ft wide with only an outer rail – very dangerous. The drop off to the grassy floor below was about 7-9 feet straight down. I was in a group of riders that suddenly saw this “tightrope” situation and jammed on their brakes. (Nobody realized we should have diverted onto a narrow, unmarked path that led downward through the lock.) Fortunately, everyone stopped safely; walked their bikes down a slope and on to the safe path through the bottom of the lock. A simple, cheap sign could prevent the near-miss accidents at this spot.
I’m really disappointed that this National Park hasn’t (at least) marked these safety hazards. Considering all the hazards and the rough gravel, I think this C&O Towpath trail merits 2 stars.

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