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 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.
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!
My friend and I went for the first time and had a blast.
I did an up and back 35 miles. Great paved trail and. It many people at this end. Looking forward to riding the rest. I hate dc traffic
04/04/2026.Great Savage Tunnel on the Great Allegheny Passage is open. Motion sensor lights to illuminate the tunnel. If you have bike lights, maybe use them inside the tunnel so other users can see your presence easier.
Tunnel is closed. I ventured over the top and it's tough
The Washington & Old Dominion is the best trail hands down. It is also one of the busiest trails that hosts running clubs, cycling clubs, nature walkers, neighborhood walkers, walking and biking commuters and is at its busiest before 7 am in extreme heat.
What makes this 44 mile trail so unique is the amenities that sit along side of it making it the best trail to plan an activity on with family and friends. Just pick a city that you want to visit and you can find convenience stores adjacent to the trail within walking distance as well as myriad of restaurants for all ages, ice cream parlors, grooming services, bike shops and over the past few years breweries have been added to the scenery right on the trail.
The location is prime to the cities of Northern Virginia with access to getting into Washington DC to see the monuments and Hains Point. Nothing beats the W&OD Trail!
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!
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