Find the top rated walking trails in Shepherdstown, whether you're looking for an easy short walking trail or a long walking trail, you'll find what you're looking for. Click on a walking trail below to find trail descriptions, trail maps, photos, and reviews.
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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.
Well maintained and shady in the summer. Pastoral views
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
I park at Maryland Ave off of MacArthur Blvd and hop on the car-free path here. Lots of lovely scenery and never crowded. Weekends there are a lot of street bikers but the pathway is always easy going. Restrooms across from Old Angler's Inn - good turn around point. Great ride.
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.
It was a foggy damp day. Very light traffic on the trail except in Shippensburg. Very, very well maintained! Some of the gravel is deeper in areas than others, which when wet causes substantial drag on the tires. Total of 26 1/2 miles from end to end as out and back.
Plentiful parking downtown and at Watkins Park on Route 27. East section is picturesque along smooth gravel, decked, and paved sections between interesting rock formations with varied vegetation. Museum in original train station depot is opposite beautifully restored caboose where right of way ends. To reach west section must walk north on Main Street and west on Prospect Road past castle to Hill Street entrance. West section is nicely paved with benches and trees carved with nature scenes. Also can walk up Hill Street, down Baker Street, and ascend stairs behind shops to reach Main Street. This will be a five star trail once the rail connecting east and west sections becomes accessible!
If your from Montgomery County this trail is perfect. You get to see so many beautiful parks, open meadows, dense forest, and it’s all along the bank of rock creek. The trail is well labeled so it’s difficult to get lost. The trail also passes by the Mormon temple, where you get to see A pearl White Castle in the distance of the trail. One thing I found challenging was the trail after rain, due to all of the trees the trail gets slippery from fallen leaves and dirt, be careful. Other than that a beautiful trail 9/10.
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