Find the top rated dog walking trails in Winchester, whether you're looking for an easy short dog walking trail or a long dog walking trail, you'll find what you're looking for. Click on a dog walking trail below to find trail descriptions, trail maps, photos, and reviews.
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I just completed walking the main trail in both directions. Two days of hiking, with about 10,000 steps each day. I started by parking in a shopping mall lot about 1/3 of a mile from the eastern end trail head. In retrospect, the trail is near residential homes. I could have parked on the street and accessed the trail with a public access point. It is a lovely trail. The one downside is that i was never really in the woods. From almost every point on the trail, one can see the back of somebody’s house. This is more pronounced on the eastern half. The prettiest is within Ellanor C Lawrence Park.
I biked from Pittsburgh to DC (GAP and C&O trails combined) 9/8 thru 9/14/24. This review is for the C&O only. Weather – excellent. Scenery- beautiful. Accommodations – very good. Trail surfaces –highly variable from narrow dirt paths laced with muddy holes to relatively smooth, hardpacked dirt to loose gravel (better for a pickup truck than a bicycle!). From 10 miles south of Great Falls into DC the trail/road was especially rough. I was riding an Off-road bike with 40 MM wide tires and momentarily lost front tire stability in MANY spots due to loose gravel (especially on the sloped paths leading into & out of lock areas). My biggest safety concern were the numerous concrete bridges over creeks & culverts that had ZERO guard rails, warning signs or even yellow paint. The bridge widths were narrower than the trail requiring the biker to NOTICE and move more to the center for safety. If a biker went off the side of any of these bridges, I’d expect serious injuries or worse. The worst safety hazard was at Lock 38. Approaching the lock from the southwest side, the (main) trail leads right across the top of the lock wall- that is 3 to 4 ft wide with only an outer rail – very dangerous. The drop off to the grassy floor below was about 7-9 feet straight down. I was in a group of riders that suddenly saw this “tightrope” situation and jammed on their brakes. (Nobody realized we should have diverted onto a narrow, unmarked path that led downward through the lock.) Fortunately, everyone stopped safely; walked their bikes down a slope and on to the safe path through the bottom of the lock. A simple, cheap sign could prevent the near-miss accidents at this spot.
I’m really disappointed that this National Park hasn’t (at least) marked these safety hazards. Considering all the hazards and the rough gravel, I think this C&O Towpath trail merits 2 stars.
My wife had a yen to do a through ride and chose the GAP trail as her goal.
We spent 5 days on the trail, starting in Pittsburgh, and finishing in Cumberland. Even with drizzling rain on several portions of the ride, we both count this as one of the best we ever rode.
The trail surface is so consistently even, it is easy rolling, especially once you cross the Eastern Continental Divide, where it steepens a bit, downhill. There was literally no trash to be found along the trail, and any debris from trees, like limbs, was quickly removed by the crews that do that. There were times when we rode many miles without seeing another rider, or crossing a road. Along the way we noticed many places to take a break, with benches or shelters, and near each trailhead you will find a bike maintenance stand, with tools and air pump. We stayed in Pittsburgh, Boston, Connersville, Confluence, Meyersdale, and finished in Cumberland. All the lodgings were very nice, and we left our vehicle at our hotel in Pittsburgh ( paid to park it there ) and hired a livery service to get us back from Cumberland to the steel city. If you are considering this trail, go do it ! It was great.
I recently walked virtually every foot of the 40+ mile long Jerry Connolly Cross County trail, in both directions. This includes the part of the route which is not a trail at all, but a 2-mile long sidewalk along a busy road. I would start by driving to a starting point and walk about 5000 steps in one direction, stopping at a convenient point where I could park my truck nearby. Then, I walked back along the same trail. Most of the southern part of the trail, from the Occoquan river to Arlington Blvd is paved in asphalt. Almost all of the northern part, from the Oakmont rec center to Great Falls park is a rough trail. This part would be quite muddy after a rain. Most of the trail parallels a stream, from Difficult Run in the north, to Accotink Creek in the middle, to Pohick Creek in the south. Trail markers range from excellent in some parts to hardly noticeable in other parts. Having Google Maps on a phone app was super helpful at times when I accidently veered from the trail, or was at a point with a fork in the trail. There are several signs along the way with a map of the trail in the near vicinity. These were necessary and helpful when the trail came to an apparent end and the resumption point was several yards away. Almost all of the trail is an easy walk with just a few steep-ish ascents and descents. Most of the trail is really quite pretty. Overall, a very fulfilling experience for me.
My wife had a yen to do a through ride and chose the GAP trail as her goal.
We spent 5 days on the trail, starting in Pittsburgh, and finishing in Cumberland. Even with drizzling rain on several portions of the ride, we both count this as one of the best we ever rode.
The trail surface is so consistently even, it is easy rolling, especially once you cross the Eastern Continental Divide, where it steepens a bit, downhill. There was literally no trash to be found along the trail, and any debris from trees, like limbs, was quickly removed by the crews that do that. There were times when we rode many miles without seeing another rider, or crossing a road. Along the way we noticed many places to take a break, with benches or shelters, and near each trailhead you will find a bike maintenance stand, with tools and air pump. We stayed in Pittsburgh, Boston, Connersville, Confluence, Meyersdale, and finished in Cumberland. All the lodgings were very nice, and we left our vehicle at our hotel in Pittsburgh ( paid to park it there ) and hired a livery service to get us back from Cumberland to the steel city. If you are considering this trail, go do it ! It was great.
My wife had a yen to do a through ride and chose the GAP trail as her goal.
We spent 5 days on the trail, starting in Pittsburgh, and finishing in Cumberland. Even with drizzling rain on several portions of the ride, we both count this as one of the best we ever rode.
The trail surface is so consistently even, it is easy rolling, especially once you cross the Eastern Continental Divide, where it steepens a bit, downhill. There was literally no trash to be found along the trail, and any debris from trees, like limbs, was quickly removed by the crews that do that. There were times when we rode many miles without seeing another rider, or crossing a road. Along the way we noticed many places to take a break, with benches or shelters, and near each trailhead you will find a bike maintenance stand, with tools and air pump. We stayed in Pittsburgh, Boston, Connersville, Confluence, Meyersdale, and finished in Cumberland. All the lodgings were very nice, and we left our vehicle at our hotel in Pittsburgh ( paid to park it there ) and hired a livery service to get us back from Cumberland to the steel city. If you are considering this trail, go do it ! It was great.
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.
Since my wife has 2 knee replacements, this spot is perfect. Maintenance is being performed (2024) so it is a little out of the norm. Trail runs along C&O towpath so switching is easy. Also eastern part close to facilities. Western part more remote. We love also the many parking areas available. Geocaches add to the adventure as well. Will return.
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.
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