Explore the best rated trails in Winchester, VA, whether you're looking for an easy walking trail or a bike trail like the Meadowlark Connector Trail and Gerry Connolly Cross County Trail . With more than 35 trails covering 4325 miles you're bound to find a perfect trail for you. Click on any trail below to find trail descriptions, trail maps, photos, and reviews.
This trail map does not show how to navigate out of Pittsburgh… specifically the first few miles with a notable gap across Smithfield Street!
Good mountain bike trail that as described in the trail overview traverses up and down the "rolling" hills with many areas of no shade. If you start up at the Germantown Soccerplex, I suggest you park near the BMX bike course and south along the tree line and you come across the starting marker for the Powerline trail (about a tenth of a mile down).
I will say it was our first Time Visiting this area. Me and my girlfriend were taken away by the beauty of the area. We didn't get to see the entire area. Also, there is this restaurant on the trail that makes the atmosphere feel like you are at peace. We are definitely going back.
Only did part of the trail from Herndon to Reston. Just watch out for the ‘Lance Armstrong’ wanna bees. Most of them do alert they are coming to your left, so stay to your right and you should be ok.
The map gave us the start of the trail. But, it was in a neighborhood and there was no parking at all.
I started my experience at the trailhead of the charming and historic town of Purcellville at 7:30 on a Saturday morning in late October. I only went about six miles, but was surprised at the amount of fitness minded people using the trail so early in the day. It was primarily walkers and runners, but every now and then serious speed demons on their bikes would race past me. It's certainly a good trail for building up speed.
As for me, a tourist from California, I was moving along the trail moderately so as to take advantage of as many photo ops as possible. I especially enjoyed the fall colors, rolling hills of farm and pasture land, and some historic, vintage buildings. The stately country homes were absolutely stunning! I wish I'd had more time to explore more of this trail further!
The trail is great starting at Cumberland. Pretty smooth and scenic. Not very far in there were quite a few detours as the trail was damaged in many places. I wish there had been more amenities along the trail. The last 40 miles into DC were surprisingly bad, with muddy rough conditions and detours. The trip was memorable and challenging and we were proud to raise money for theplummerhome.org for homeless veterans.
Day1: DC to Williamsport. Day 2: Williamsport to Cumberland. This was an amazing ride with beautiful fall scenery. Trail was well maintained and easy to navigate. It was mostly hard parked gravel with lots of historical sites and great views. Paw Paw tunnel was open. The trail thru tunnel is uneven and wet. Met some great people along the trail. I’ll definitely ride the trail again in the summer.
We took the Amtrak bike train to DC. Had to switch trains in Philly. Between Harrisburg and Philly we had to remove the front wheel and hang the bike. From Philly to DC they were stored in the baggage car and didn't require tire removal. The ride through DC was fantastic and much easier than we expected. The trail got a little confusing to get out of town but once we did we found the trail in much better condition then we expected. We stayed along the way in a hotel and a lock house. My favorite part was the area around the pawpaw tunnel but the trail was in very poor condition in spots. At one point when I tried to go my rear wheel would just spin and the bike wouldn't move. Very mucky and muddy. I'm sure it all depends on the amount of rain they had recently. It completed the ride from Pittsburgh to DC for me. I had ridden the GAP trail about 6 years prior. The only reason I didn't give it a five star rating is because of the mud in some areas. Overall it was great.
Because of the rainy weather before we arrived, we decided to do this trail instead of the muddy C and O Towpath. There were some tree roots riding from New Orleans to Hancock, but the vistas and beauty of the fall ride made up for it. We are leisurely cyclists with hybrid tires.
All I wanted to do was get from the Springfield Metro Station to Springfield - by Sydenstricker/Rolling Road. It's really unclear (or at least on both my GPS apps) on how to get back. Bike baths just kept ending and there was no sign (that I could see) indicating an alternate path, I had to weave thru neighborhoods guessing - but again w/no real signs and sometimes it just felt like it kept leading me again and again to the parkway. A few more signs, a bit more clarity. I've never struggled with a path so much and I bike all over MD, DC and VA. I seriously went around in circles around Hooes and Rolling for over 1.5 hours. I finally just biked on the emergency lane on the Parkway to get to Backlick.
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