Explore the best rated trails in Shepherdstown, WV, whether you're looking for an easy walking trail or a bike trail like the Meadowlark Connector Trail and Ox Road Sidepath . With more than 59 trails covering 4347 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.
Well maintained and shady in the summer. Pastoral views
Well maintained and shady in the summer. Pastoral views
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.
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.
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