Find the top rated cross country skiing trails in Winchester, whether you're looking for an easy short cross country skiing trail or a long cross country skiing trail, you'll find what you're looking for. Click on a cross country skiing trail below to find trail descriptions, trail maps, photos, and reviews.
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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.
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!
I decided to park in Cumberland on my way home from a trip to WV and ride down the C&O towpath to ride this trail.
I was disappointed in the state of the trail. It appears as if no one is maintaining this trail.
The path on the Maryland side is now almost covered with encroaching weeds.
The bridge is in good enough shape to permit you to ride across to West Virginia for the time being but it looks a little iffy. If no one is taking care of this trail the wooden planks may need replacing. At some point it may become a dangerous crossing when these planks start rotting.
The tunnel is blocked off so you can go no further than the WV side of the bridge.
I would recommend that riders skip this trail until such time as it is maintained.
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