Explore the best rated trails in Winchester, VA, whether you're looking for an easy walking trail or a bike trail like the Chesapeake & Ohio Canal National Historical Park and Western Maryland Rail Trail . With more than 36 trails covering 4328 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.
Just got done this trail 10/9. Gap trail is a wonderful easy ride. Places we stayed were awesome! Bright Morning B&B, Ohiopyle suites. We stayed in the Karly. It was great! Right off the trail!! Coffee shop is great too. They also have a laundromat. We then traveled to Meyersdale where we stayed in the hotel airstream! Gotta stay here! It was great! Know that if you need to take the train back to Pittsburgh like we had too, it can run late. 5hrs for us. We met so many nice people along the way. That’s what I think of when I think of this trail!
I decided to park in Cumberland on my way home from a trip to WV and ride down the C&O towpath to ride this trail.
I was disappointed in the state of the trail. It appears as if no one is maintaining this trail.
The path on the Maryland side is now almost covered with encroaching weeds.
The bridge is in good enough shape to permit you to ride across to West Virginia for the time being but it looks a little iffy. If no one is taking care of this trail the wooden planks may need replacing. At some point it may become a dangerous crossing when these planks start rotting.
The tunnel is blocked off so you can go no further than the WV side of the bridge.
I would recommend that riders skip this trail until such time as it is maintained.
This is probably the most I could handle on a bike ride. We rode the GAP and C&O back to back like many do in 8 days. It was great fun but the C&O is noticeably rougher, fewer port-a-Johns and very scarce potable water sources. On our 7th day from Williamsport to Brunswick we ran out of water midway and rode the remaining 25 miles without water. Fortunately the shade offered by the beautiful canopy of trees made it bearable. We made sure to load up on extra water on our final day. The mix of loose sand that caught us by surprise & the larger stones on the trail made for a more challenging ride than expected. On the one rainy day we had from Cumberland to Little Orleans, some of the puddles we encountered offered a new sense of “oh dear” as we didn’t know how deep the hole we were riding thru when there was no room to go around the puddle.
I just completed the entire GAP. It was well worth it. The trail was in good shape and there was not too much traffic. I’d like to do it again.
Biked from Hancock to Little Orleans and return on August 30, 2025. Distance: 34.5 miles. Stopped for lunch at Bill's Place in Little Orleans and got good food and friendly service. The paved portion of the trail is in excellent condition -- thanks to the Maryland Park Service for recently repaving the trail. The only negative is the 3-mile detour on the C & O Canal towpath around the abandoned Indigo tunnel. The towpath detour is unpaved and has a rougher surface than the trail. The nearly one-mile long tunnel was closed in 2010 to protect a handful of bats allegedly living inside. The tunnel is an engineering marvel that should be seen and experienced by humans. Opening it to trail users would help the economically depressed Western Maryland area. For example, the equally-long Blue Ridge Tunnel in Afton, Virginia, draws about 50,000 visitors annually since it was reopened in 2020.
there are some really old bridges that go over the C&O. the highlight is the paw paw tunnel. better to walk through it. once you hit little orleans, i suggest going on the western maryland trail. it is fully paved and nice.
hancock is a great town
Riding on this was a bucket list trail. Had hoped to ride further on it but had time restraints. Great trail. The rest stop in Meyersdale is wonderful. Plan someday to return and ride more of it.
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.
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.
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.
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
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