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 Fairfax County Parkway Trail. With more than 33 trails covering 4312 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.
For scenic views and a step back in time this trail is a must. It's muddy, especially right after rain. We avoid our e-bike on this trail due to the mud, but it's mainly flat. Paw paw tunnel is a must see, but it's nothing out there along the way. Harpers Ferry is gorgeous and historic. Bring your Bug Guard you'll need it. And your swim tube.
I have ridden my fair share of rail trails and the GAP is the best rail trail I've ever experienced. I started in Cumberland and finished in Pittsburgh. I knew what I was getting myself into riding against the Eastern Continental Divide but I got the harder riding done right away. I spent three days on the trail staying overnight in Confluence, Smithton and ending in Pittsburgh taking Amtrak back to my car in Cumberland.
The GAP offers so much variety over its 149 miles from scenic river views, sweeping mountains, ruins of a mining past to human development from a rural to urban scale. Most of the trail is very tightly packed gravel which is in immaculate shape. For the first few miles out of Cumberland and the last twenty or so miles to Pittsburgh the trail is asphalt.
I went on my ride in mid-May right before peak riding season so while many businesses in the trail towns were open many still had limited hours. Riding during peak season will give you even more options to eat, stay and shop. Every town I visited were very bike friendly (I've never seen so many places to lock your bike), with plenty of signage to share the road and locals very happy to see tourism in their communities. Some of the smaller towns like Smithton and Boston are not heavily highlighted but still offer dining and places to stay overnight.
There are many bike fix-it stations located on the GAP. While I expected to see some in the trail towns I was surprised by the abundance of fix-it stations located outside of towns as well. There are bathrooms (a mix of businesses, port a pots and composting toilets) roughly every ten miles. Most trail towns had a store to buy refreshments and I did notice a few restaurants had no issue with filling up a water bottle for any who asked.
My least favorite part of the trail was the last twenty miles from Boston to Pittsburgh. The asphalt in this section is in pretty good shape but in comparison to over 100 miles of smooth gravel it is rough. McKeesport is a sudden shift to an urban environment with a fair amount of on road riding but it is well marked and I had no issues navigating and I felt safe. I had issues navigating in Pittsburgh as I felt the clear marking that helped me navigate McKeesport was non-existent. Also to note is the on-road detour to Point State Park. It is easy to follow if you have a map but it requires riding in a major city for a short distance.
I have ridden many trails, a few that are in the Rail Trail Hall of Fame. The GAP is by far the best and is truly the ride of a lifetime.
Trail was in great condition and it is a beautiful ride.
Bright Morning Bed and Breakfast was a definite highlight of my GAP ride last summer. It’s right on the trail and had a great purpose built bike shelter building. Oh yeah, the breakfast the next morning was fabulous!
Surprised to see this amazing trail that has great bed and breakfasts along it is not noted as part of the Great American Rail Trail. It sure would help demonstrate more GART completion if it was.
I just returned from my third ride on the Western MD. I've ridden the entire trail and it's great to get in a half century ride. Starting from Little Orleans one can ride west a short distance to a gate at a high bridge over the Potomac River. West Virginia has not completed any of the proposed section to the west. Riding back east after a short distance you reach the blocked off Indigo Tunnel. The tunnel is blocked due to endangered bats. A zig-zag ramp leads down to the C&O Towpath. You ride the towpath about 2.5 miles and take a similar zig-zag ramp back up to the Western MD. Except for this detour the entire route is paved asphalt. There are areas of either frost or root heaves but not too bad. When the leaves are off there are nice views of the C&O Towpath, the canal and the Potomac. Most of the path is in the woods with a few fields here and there. At times the trail runs along a high, narrow path pretty high above the river. There are historical markers, some benches and a small shelter or two. The first, and only town on the trail is Hancock, MD. It is about half way between the endpoints. There are the regular amenities not far off trail such as a few fast food joints and a Sheetz. The top attraction for trail eats is Buddy Lou's right on the trail and at a cross-over to the C&O. Needless to say it gets busy in the summer. Buddy Lou's isn't open every day however so plan accordingly. There is also a bike shop in town right by the trail. After Hancock its a fairly straight run to the end at Big Pool. Some this section is close to I70 and some very close (less than 20 ft) so there can be a bit of traffic noise. This is my least favorite part and would probably rate the trail at 4.5 stars if I could. At Big Pool there is a parking area plus some benches, a restroom and a bike repair station. It's a nice place for a lunch break if you're doing a round trip. All together I can wholeheartedly recommend the Western MD. We have even used it as the half of a loop with the other half on the C&O.
I enjoyed being able to get used to my Catrike Villager on a paved trail, close to a town yet still adjacent to farm fields and Antietam Creek. I was able to practice shifting gears on various uphills and downhills. I will definitely visit this again!
This trail is mostly paved and runs through varied terrain. It travels along a creek, through the woods, near an old repurposed prison, and several neighborhoods. I started at the Southern terminus. Time only allowed me to ride the southern 10 miles (10 out and 10 back). Although paved, I’d recommend a hybrid, gravel, mountain or comfort bike of you are biking it. There are rooted areas and some creek crossings with cement stepping areas to get across. There were very few on the trail on the Wednesday afternoon that I wenrX There are some tricky forks in the path. Make sure you have a map or app accessible.
I have done the C&O/GAP trip 4 or 5 times now and loved it every time. everyone is friendly and on the C&O you can go as little or as far as you want per day. Camping areas every 10 miles so you cant get yourself stuck.
I love the GAP but prefer the C&O because its more of a trail vs just spinning away road ridding like always. Much of the C&O feels like you are in the woods away from things but without ever really being far should you need help. its the perfect amount of "adventure" for normal people.
Don't over pack, towns and stops all along the trial. Its flat so its easy to over do it.... but once you hit the PawPaw detour you will question if you really needed the laptop, espresso machine, and mini fridge :)
Test ride your bikes loaded, make sure its still fun to ride and remove the silly stuff you really don't need.
Bring/try and keep 3 water bottles full in case a pump or two is out, and drink more than you think you need to
bring snacks and eat more than you think you need to
ride a bike with around 38c-50c (1.5"-2") tires and do not pump them up to the max pressure listed on the sidewalls. that number on the side of the tire is the maximum and not even close to ideal pressure (google tire pressures for dirt roads on bikes), not a rule, you can totally go with thinner tires, I had no problem with my 32c tires last time but it is far more comfortable with a bit more rubber between you and the trail especially if you don't ride all the time.
Makes me sad when I see people complain about the C&O trail surface, thats why I go.... We have millions of miles of road to ride starting at our doorsteps why make more. Just use the proper tire and pressure for a TRAIL and your golden.
I can’t describe how much I love this trail. It goes longer than anyone could ever want and the people are courteous and everyone looks to be having a great time.
This is a very good trail. It would be better if it went through the old tunnel and was extended over the Potomac with the existing bridge. Very remote from the little orleans side.
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