Find the top rated walking trails in Winchester, 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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We rode the GAP from Cedar Creek Park to the Boston trailhead at the base of the Historic Boston Bridge and back. About 36 miles round trip. What a great ride. Smooth trail with lots of benches and several picnic areas and toilet facilities. Well maintained. Passed through several little communities along the trail. No major highways and very few little roads to cross making it very safe. Got a delicious huge “medium” size ice cream cone at the “Big Twist” in Blythedale, right off the trail. Highly recommend this ride!
Went out today (6Sept26) on my recumbent trike and I went to the Connellsville trailhead by the Martins grocery. That is the old train station and is well set up with lots of parking, restrooms, and camp sites. I took the trail toward Ohiopyle and it was just peaceful as can be. A good many riders on the trail, but everyone was courteous. The trail is well maintained, although maybe a little narrow in spots. Try it out sometime for yourself. Enjoy!
I enjoyed the ride. A lot to see and do since trail goes through part of Luray. Good parking areas and friendly people along trail.
We were just passing through the area and wanted to do a quick bike ride. Began at the Big Pool trailhead (MM0). Cycled about 8.5 miles before turning around. This section of the trail was nicely paved and shaded. As others mentioned, the one drawback was at about MM2, the trail parallels the freeway and it is quite noisy. However, we were aware of this when we started. If I was passing through the area again, I would try another section of the trail.
Discovered this comfortable place with great accommodations for two bike travelers. They offer a pullout sofa if you do not wish to share a bed. Indoor bike storage with a comfy bed and a hot shower! Distillery right next-door and two restaurants to fuel up in the morning to get back on the trail. Close to the panhandle of West Virginia. Their name is Harmony Trail Haven on Airbnb.
We went on a Sunday at the end of May. The weather was perfect and the trail was impeccable. We didn’t go the entire way- we went 15 miles up and then turned around so we didn’t see the tunnel. The honeysuckle was in bloom and the entire trail smelled heavenly. We stopped for lunch at Buddy Lou’s - it’s right on the trail and we highly recommend it. We sat outside on the balcony for lunch and could watch the other cyclists and runners on the trail while we ate in the sunshine. The trail is pretty shaded in many spots so even in warm weather you’d have a comfortable ride. I was surprised, considering the perfect weather and what a great trail it is that it wasn’t busier. This is 10 out of 10 for a great trail experience.
The GAP trail was amazing. The nicely maintained 150 mile trail along the Pennsylvania mountains and rivers and then the descend into the Cumberland Valley was the best! We took it easy planning to only ride around 30 miles a day staying in Airbnb’s along the way. We rode it in 5 days and spend an extra day in Cumberland and did a 15 mile out and back along the C&O. We rented bikes ahead of time with the Golden triangle in Pittsburgh. they fitted the bikes out for us and provided a shuttle ride back to Pittsburgh for the bikes and us. We are looking forward to doing more trails in this area.
This is one of the nicest trails out there. Lots of elevations changes and a nice brewery ( caboose brewery) along the way. I did the upper end a few weeks before and the lower end later. Lots of rest stops and bathrooms. Nice towns until you get to the dc area and it all looks the same.
Bike touring across tha US and I’m currently set in my hammock about 10 mils outside of frostbite head West! Gotta say that MD & PA has out done themselves on tha GAP! Wish other places “you kno who you are WV, yea you! Anyway, I love its backcountry vibe and tha fact that it’s well maintained! Hope tha rail to trail route gets done sooner rather than later and is maintained this well instead of corrupt politicians pocketing tha money! You kno who you are, you! Anyway, to tha hiker and biker trash out there, one love!
Highly recommend this beautiful and well kept trail. Beautiful to ride along the trees and over the 2 epic ohiopyle bridges.
First time my friend and I have trail skated! This was so fun, especially for 2 67 yr. olds!! Saw lots of walkers, bikers, etc., everyone was friendly, beautiful scenery, squirrels and birds everywhere, great place to rollerskate!
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