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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If you have researched the GAP at all, you already know this was among the first trails inducted into the Rails-to-Trails Conservancy Hall of Fame. Many riders continue to go back to ride it again. That speaks volumes to the experience of riding this trail. If you are an end-to-end rider, and not a camper, you will need accommodations. I would like to highly recommend Cardinal's Roost B&B in Rockwood, PA. You will not find more amiable hosts than Jennifer and Chris. The accommodations are spotless, comfortable, and tastefully decorated. The breakfast is out of a 5-star restaurant. They have a huge garage to store your bikes with plenty of space to do maintenance if need be. Jennifer and Chris are bicyclists themselves so they understand needs of cyclists. If passing through Rockwood on the GAP or just enjoying the beautiful scenery, you cannot go wrong with Cardinal’s Roost.
The best part of the WOD is west of Leesburg, through Paeonian Springs into tunnels of trees, past farmland, ending at a fabulous barbecue place in Purcellville. Stunning in fall foliage.
Rode from Cumberland to a parking area 23 miles outside of DC, camping at four of the campsites along the way. They have been doing a lot of work to improve the condition of this trail and it shows. Weather was perfect, but most sections seemed like they would still be pretty good even after some rain. There was one detour that was a tough push over really rocky roads for a few miles. Other than that, it was perfect.
We ( recumbent trike & e-bike) headed West from the Kiwanis park. Turned around after 9km as the surface was really tough on the trike. There’s 2 good wheel tracks for bikes, but the trike had to ride partially in the coarse trail ballast. Scenic area with farm views and a huge windmill farm in the distance.
I headed out of Pittsburgh Point State Park 8/6/2024 for a day ride to Homestead and back. I quickly ran into large homeless encampments along the Three Rivers Heritage Trail portion of the GAP. No one approached me but the trash, the smell of urine and tents almost on the trail were discouraging and I ended my ride and drove home. I might suggest anyone planning to ride that section of the GAP check the current conditions before proceeding. From what I found online once I got home was that it does not appear to be a short term problem. Other riders have commented on open drug use and the concern for unleashed dogs. I could not find a go around from local riders’ comments.
On the way down we rode the rail trail. It’s was 90% trees and concrete path. Hancock was a cute little town tho and we stopped at the Blue Goose Market that was cute. We rode the tow path on the way back and I thought that was slightly better for the scenery. It was a gorgeous day to be out but I’ve been on better trail.
We parked at lock 38 by Shepardstown. Trail is well maintained and gorgeous. Many bikers, runners and walkers out.Note it is a trash free park.
Most of this trail is not along streets. We often ride this trail round trip from Ballenger Creek Park to the other end which is near Dunkin Donuts. We often see deer. There are two bridges over Ballenger Creek, and an underpass at New Design Road which keeps trail users away from traffic. There are a few air pump and tool stands along the trail. The western half mile is on sidewalk along the road, with traffic light protection for crossing.
The amazing smell of the flowers at the start of the trail would be worth another ride for that alone. (We started at Welty Road Park.) Lots of hills, definitely a workout, some shade and some sun. The creek is absolutely beautiful.
From Dupont Circle in DC out to Purcellville in VA is almost exactly 50 miles. So hard core cyclists can do a century, while less extreme pedalers can make a two day trip out of it. And, as there are many Metro stops along the trail, cyclists can also do rides of varying lengths along different sections. An amazingly versatile trail in that regard. All of which — plus the C&O Canal (360 miles r/t from DC to Cumberland), Mt Vernon Trail (42 miles rt from DC to Mt Vernon), Rock Creek Park trail (45 miles rt from DC to Lake Needwood) should make DC the top cycling destination in the US.
One of the top 10 bucket list rides in the US, easily. And when combined with another, the C&O Canal, you can cycle on dedicated bike paths for 330 miles from DC to Pittsburgh. The 150 miles of the GAP ribbons through pristine forest, past former railway towns being resurrected by all the cycling tourists using the trail.
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