Find the top rated running trails in Winchester, whether you're looking for an easy short running trail or a long running trail, you'll find what you're looking for. Click on a running trail below to find trail descriptions, trail maps, photos, and reviews.
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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.
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.
We just finished the GAP trail & C&O towpath 9/20 from Pittsburgh to DC. We took 8 days and our days ranged between 32 miles to 63 miles. Highly recommend this trail. Well maintained, accessible and clean port a John’s, always had plenty of toilet paper and were frequent enough to remove any anxiety about not being able to relieve yourself in privacy. Potable water was available along the trail which we still used a filter just to be safe. Beautiful trail, friendly riders and towns to visit. We rented a full sized SUV in DC and dropped it off at the Budget on Stanwix St just two blocks from fountain starting point. Worked perfectly to get going on our ride without delay.
This is probably the most I could handle on a bike ride. We rode the GAP and C&O back to back like many do in 8 days. It was great fun but the C&O is noticeably rougher, fewer port-a-Johns and very scarce potable water sources. On our 7th day from Williamsport to Brunswick we ran out of water midway and rode the remaining 25 miles without water. Fortunately the shade offered by the beautiful canopy of trees made it bearable. We made sure to load up on extra water on our final day. The mix of loose sand that caught us by surprise & the larger stones on the trail made for a more challenging ride than expected. On the one rainy day we had from Cumberland to Little Orleans, some of the puddles we encountered offered a new sense of “oh dear” as we didn’t know how deep the hole we were riding thru when there was no room to go around the puddle.
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