Explore the best rated trails in Winchester, VA, whether you're looking for an easy walking trail or a bike trail like the Meadowlark Connector Trail and Gerry Connolly Cross County 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.
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.
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
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.
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.
The railroad bridge appears to be the only way to access the C&O Canal Towpath directly from Harpers Ferry. It's narrow and congested in the warmer months, and walking a bike across the bridge can be challenging. More difficult is the tight spiral staircase descending to the towpath from the bridge. It's not exceptionally strenuous with a light bicycle but I wouldn't attempt it with a heavy E-bike. Once at the bottom, the towpath is a beautiful cycling experience and it's also an easy walk to the Maryland Heights trail with its Civil War fortifications and fantastic overlook of Harpers Ferry.
I just completed walking the main trail in both directions. Two days of hiking, with about 10,000 steps each day. I started by parking in a shopping mall lot about 1/3 of a mile from the eastern end trail head. In retrospect, the trail is near residential homes. I could have parked on the street and accessed the trail with a public access point. It is a lovely trail. The one downside is that i was never really in the woods. From almost every point on the trail, one can see the back of somebody’s house. This is more pronounced on the eastern half. The prettiest is within Ellanor C Lawrence Park.
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.
We started in Akron and rode about 18 miles north. Loved it!!!
My wife had a yen to do a through ride and chose the GAP trail as her goal.
We spent 5 days on the trail, starting in Pittsburgh, and finishing in Cumberland. Even with drizzling rain on several portions of the ride, we both count this as one of the best we ever rode.
The trail surface is so consistently even, it is easy rolling, especially once you cross the Eastern Continental Divide, where it steepens a bit, downhill. There was literally no trash to be found along the trail, and any debris from trees, like limbs, was quickly removed by the crews that do that. There were times when we rode many miles without seeing another rider, or crossing a road. Along the way we noticed many places to take a break, with benches or shelters, and near each trailhead you will find a bike maintenance stand, with tools and air pump. We stayed in Pittsburgh, Boston, Connersville, Confluence, Meyersdale, and finished in Cumberland. All the lodgings were very nice, and we left our vehicle at our hotel in Pittsburgh ( paid to park it there ) and hired a livery service to get us back from Cumberland to the steel city. If you are considering this trail, go do it ! It was great.
TrailLink is a free service provided by Rails-to-Trails Conservancy (a non-profit) and we need your support!
Scan the QR code to get TrailLink on your phone
