Winchester, VA Cross Country Skiing Trails and Maps

453 Reviews

Looking for the best Cross Country Skiing trails around Winchester?

Find the top rated cross country skiing trails in Winchester, whether you're looking for an easy short cross country skiing trail or a long cross country skiing trail, you'll find what you're looking for. Click on a cross country skiing trail below to find trail descriptions, trail maps, photos, and reviews.

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Length
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8 Results
Activities
Length
Surfaces
Type

Chesapeake & Ohio Canal National Historical Park

184.5 mi
State: DC, MD
Brick, Concrete, Crushed Stone, Dirt

Cross County Trail (VA)

40 mi
State: VA
Asphalt, Ballast, Concrete, Crushed Stone, Dirt, Gravel

Great Allegheny Passage

150 mi
State: MD, PA
Asphalt, Concrete, Crushed Stone, Dirt, Gravel

Great American Rail-Trail

3743.9 mi
State: DC, IA, ID, IL, IN, MD, MT, NE, OH, PA, WA, WV, WY
Asphalt, Concrete, Crushed Stone

H & F Trolley Trail

0.72 mi
State: MD
Asphalt

Warrenton Branch Greenway

2 mi
State: VA
Asphalt

Western Maryland Rail Trail

27.5 mi
State: MD
Asphalt
Trail Image Trail Name States Length Surface Rating
Following the Potomac River, the C&O Canal Towpath traverses the Chesapeake & Ohio Canal National Historical Park for 184.5 miles between Georgetown in Washington, D.C., and Cumberland, Maryland. For...
DC, MD 184.5 mi Brick, Concrete, Crushed Stone, Dirt
The Cross County Trail is a multi-use trail that generally follows the various stream valleys in Fairfax County, Virginia. It is officially named the Gerry Connolly Cross County Trail in recognition...
VA 40 mi Asphalt, Ballast, Concrete, Crushed Stone, Dirt, Gravel
The Great Allegheny Passage (GAP) is an iconic rail-trail that runs 150 miles from Cumberland, Maryland, to Pittsburgh, Pennsylvania, and was built in partnership between state agencies and many local...
MD, PA 150 mi Asphalt, Concrete, Crushed Stone, Dirt, Gravel
Note: This developing route is not yet fully contiguous – it is just over 50% complete. Please refer to the Trail Map for more information on the existing sections of trail, as well as the online...
DC, IA, ID, IL, IN, MD, MT, NE, OH, PA, WA, WV, WY 3743.9 mi Asphalt, Concrete, Crushed Stone
Sitting on the corner of East Main Street and Alley 5 in Thurmont is a green and white one-story building. Murals decorate its walls, depicting the history of the famous Hagerstown and Frederick...
MD 0.72 mi Asphalt
The Warrenton Branch Greenway follows a segment of the former Warrenton Branch Spur railroad, running between downtown Warrenton (at S. 4th Street) and Meetze Road. The Warrenton Branch was...
VA 2 mi Asphalt
The Washington & Old Dominion Trail (W&OD) is one of suburban Washington, D.C.'s most popular rail-trails. The heavily used trail is frequented by commuters and recreationists alike, and is a...
VA 45 mi Asphalt, Crushed Stone
Plan a full day (or two) for your visit to the Western Maryland Rail Trail (WMRT), a 26-mile paved route that will take you through several eras of American history. You can access this trail from...
MD 27.5 mi Asphalt

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Trails by activity

Great Allegheny Passage

MD,PA - 150 miles

The Great Allegheny Passage (GAP) is an iconic rail-trail that runs 150 miles from Cumberland, Maryland, to Pittsburgh, Pennsylvania, and was built in partnership between state agencies and many local...

Chesapeake & Ohio Canal National Historical Park

DC,MD - 184.5 miles

Following the Potomac River, the C&O Canal Towpath traverses the Chesapeake & Ohio Canal National Historical Park for 184.5 miles between Georgetown in Washington, D.C., and Cumberland, Maryland. For...

Washington and Old Dominion Railroad Regional Park (W&OD)

VA - 45 miles

The Washington & Old Dominion Trail (W&OD) is one of suburban Washington, D.C.'s most popular rail-trails. The heavily used trail is frequented by commuters and recreationists alike, and is a...

Cross County Trail (VA)

VA - 40 miles

The Cross County Trail is a multi-use trail that generally follows the various stream valleys in Fairfax County, Virginia. It is officially named the Gerry Connolly Cross County Trail in recognition...

Accordion

Great American Rail-Trail

DC,IA,ID,IL,IN,MD,MT,NE,OH,PA,WA,WV,WY - 3743.9 miles

Note: This developing route is not yet fully contiguous – it is just over 50% complete. Please refer to the Trail Map for more information on the existing sections of trail, as well as the online...

H & F Trolley Trail

MD - 0.72 miles

Sitting on the corner of East Main Street and Alley 5 in Thurmont is a green and white one-story building. Murals decorate its walls, depicting the history of the famous Hagerstown and Frederick...

Western Maryland Rail Trail

MD - 27.5 miles

Plan a full day (or two) for your visit to the Western Maryland Rail Trail (WMRT), a 26-mile paved route that will take you through several eras of American history. You can access this trail from...

Warrenton Branch Greenway

VA - 2 miles

The Warrenton Branch Greenway follows a segment of the former Warrenton Branch Spur railroad, running between downtown Warrenton (at S. 4th Street) and Meetze Road. The Warrenton Branch was...

Western Maryland Rail Trail

MD - 27.5 miles

Plan a full day (or two) for your visit to the Western Maryland Rail Trail (WMRT), a 26-mile paved route that will take you through several eras of American history. You can access this trail from...

Warrenton Branch Greenway

VA - 2 miles

The Warrenton Branch Greenway follows a segment of the former Warrenton Branch Spur railroad, running between downtown Warrenton (at S. 4th Street) and Meetze Road. The Warrenton Branch was...

Washington and Old Dominion Railroad Regional Park (W&OD)

VA - 45 miles

The Washington & Old Dominion Trail (W&OD) is one of suburban Washington, D.C.'s most popular rail-trails. The heavily used trail is frequented by commuters and recreationists alike, and is a...

Cross County Trail (VA)

VA - 40 miles

The Cross County Trail is a multi-use trail that generally follows the various stream valleys in Fairfax County, Virginia. It is officially named the Gerry Connolly Cross County Trail in recognition...

Accordion

Great Allegheny Passage

MD,PA - 150 miles

The Great Allegheny Passage (GAP) is an iconic rail-trail that runs 150 miles from Cumberland, Maryland, to Pittsburgh, Pennsylvania, and was built in partnership between state agencies and many local...

Great American Rail-Trail

DC,IA,ID,IL,IN,MD,MT,NE,OH,PA,WA,WV,WY - 3743.9 miles

Note: This developing route is not yet fully contiguous – it is just over 50% complete. Please refer to the Trail Map for more information on the existing sections of trail, as well as the online...

Chesapeake & Ohio Canal National Historical Park

DC,MD - 184.5 miles

Following the Potomac River, the C&O Canal Towpath traverses the Chesapeake & Ohio Canal National Historical Park for 184.5 miles between Georgetown in Washington, D.C., and Cumberland, Maryland. For...

H & F Trolley Trail

MD - 0.72 miles

Sitting on the corner of East Main Street and Alley 5 in Thurmont is a green and white one-story building. Murals decorate its walls, depicting the history of the famous Hagerstown and Frederick...

Great American Rail-Trail

DC,IA,ID,IL,IN,MD,MT,NE,OH,PA,WA,WV,WY - 3743.9 miles

Note: This developing route is not yet fully contiguous – it is just over 50% complete. Please refer to the Trail Map for more information on the existing sections of trail, as well as the online...

Washington and Old Dominion Railroad Regional Park (W&OD)

VA - 45 miles

The Washington & Old Dominion Trail (W&OD) is one of suburban Washington, D.C.'s most popular rail-trails. The heavily used trail is frequented by commuters and recreationists alike, and is a...

Cross County Trail (VA)

VA - 40 miles

The Cross County Trail is a multi-use trail that generally follows the various stream valleys in Fairfax County, Virginia. It is officially named the Gerry Connolly Cross County Trail in recognition...

Warrenton Branch Greenway

VA - 2 miles

The Warrenton Branch Greenway follows a segment of the former Warrenton Branch Spur railroad, running between downtown Warrenton (at S. 4th Street) and Meetze Road. The Warrenton Branch was...

Accordion

H & F Trolley Trail

MD - 0.72 miles

Sitting on the corner of East Main Street and Alley 5 in Thurmont is a green and white one-story building. Murals decorate its walls, depicting the history of the famous Hagerstown and Frederick...

Chesapeake & Ohio Canal National Historical Park

DC,MD - 184.5 miles

Following the Potomac River, the C&O Canal Towpath traverses the Chesapeake & Ohio Canal National Historical Park for 184.5 miles between Georgetown in Washington, D.C., and Cumberland, Maryland. For...

Western Maryland Rail Trail

MD - 27.5 miles

Plan a full day (or two) for your visit to the Western Maryland Rail Trail (WMRT), a 26-mile paved route that will take you through several eras of American history. You can access this trail from...

Great Allegheny Passage

MD,PA - 150 miles

The Great Allegheny Passage (GAP) is an iconic rail-trail that runs 150 miles from Cumberland, Maryland, to Pittsburgh, Pennsylvania, and was built in partnership between state agencies and many local...

Recent Trail Reviews

Great Allegheny Passage

The spectacular GAP...

October, 2021 by 7s5a692x35

In Pittsburgh, if you are cycling enthusiast, you must experience Bicycle Heaven - It is a nonprofit, private collection with over 5,000 complete bikes and even more bicycle parts that it is overwhelming. Some bikes date back to the late 1800s to the present.

Departing Pittsburgh’s concrete jungle, I highly recommend that you have the GAP route available on a GPS device as it is marked but you can miss the signs as you are focused on the traffic. Once on the gravel portion, it is an easy navigation exercise!

At the trailheads, there were plenty of new bicycle repair/air pump stations.

The illuminated 3,000’+ Savage Tunnel was an amazing experience as was experiencing the Mason Dixon Line.

Also, confirm (call) your dining options along the trail as even if sites on the internet say they will be open during your visit, you may be disappointed and going hungry due to staffing issues.

Cross County Trail (VA)

GT/cross-county Trail Markers are almost non-existant

October, 2021 by fsgregs

I took my bike and started up this trail from its terminus at the Occoquan Marine Park near Lorton, VA. For the 1st mile, it was obvious, a nice paved trail heading inland slightly up hill. After a mile, I encountered a cross-walk. There was NO marker on the other side, but I assumed the trail continued there. It then went into and around the side of the old Lorton Prison, which is now called the Workhouse complex. Within the complex, the trail ... just came to a stop at a parking lot. No signs, no arrows ... no anything. The map which Traillink provides showed no clear detail of where to go next. I asked 3 people, none of whom had any idea. I biked around all the buildings, went out onto the street, found nothing, and got ready to quit. Then, I talked to a biker who said to find the trail, I had to go out onto a main road (Workhouse Rd.), turn right, and I'd eventually find some signs. I biked over a mile, went into another park and biked around, and found nothing. Finally, I saw what looked like the trail, going UNDER the main road through a tunnel. Biked back up Workhouse Rd, eventually found a small branch off the road with a small GT trail sign in the back, followed its paved trail, only to find it dead-ending. Backtracked and discovered I had to branch off the paving onto a dirt trail to keep on the GT trail. Took it for 1/2 mile, came to a fork in the trail, but again, no sign as to which fork to take. I then gave up in disgust, and biked back to my car.

This trail markers are very poor. Fairfax Cty is a major well-maintained municipality. One would think its major cross-county trail would be reasonably marked. Its not. Thoroughly disgusted!!!

Chesapeake & Ohio Canal National Historical Park

Finally did the C&O

October, 2021 by pwalaski

Most of the recent reviews are spot on. If you are used to crushed limestone or asphalt the bulk of this trail is bumpy and full of exposed rocks, ruts and tree roots. The downside is you have to keep your eyes front and center most of the time. The Paw Paw Tunnel detour is a real challenge. I only had two panniers that were not full and it was a struggle. Can’t imagine how the fully loaded bike packers did it. (But I’ve also not done any mtb, so that could affect how easy/hard it was.) But the amount of history and really cool places to stop and explore make it worth it. Beautiful aqueducts and lock houses as w.landmarks makes up fo me the trail conditions.

Accordion

Chesapeake & Ohio Canal National Historical Park

What a history filled experience...

October, 2021 by 7s5a692x35

***ATTENTION***
The Paw Paw detour due to the tunnel being closed which with talking to the construction crew, will remain closed for another 18 months (Spring ’23) but when reopened, it will have a new riding surface.

The marked detour is not like any other that I have ever experienced on a trail which normally is a divert to local roads until you can rejoin the trail. Eastbound is best described as a mountain bike trail which is narrow in sections and at a 10 to 15 percent grade with exposed roots, rock gardens (rocks vertically embedded in the trail surface) and other obstacles. With a bike loaded down with gear, it is extremely strenuous to make it to the top and over the tunnel. Just pushing your bike up and over East bound is a challenge also.

Westbound is a trail that is a large enough for a vehicle but also has 10 to 15 percent grades but has a loose surface for a majority of it.

From Cumberland to Paw Paw, the trail is need of maintenance as there is numerous hazards to include mud holes that are deep (10” to 12”), segments of large branches and this time of the year with leaves falling, they hide some of the obstacles. You must keep your eyes on the trail and not sightsee for this section of C&O.

Also, confirm your dining options along the trail as even if sites on the internet say they will be open during your visit, you may be disappointed and going hungry due to the lack of staffing.

The rest of the trail is in great condition to DC and be aware as you approach the Capitol and it is on a weekend that there will be plenty of trail traffic as they enjoy this gem in their backyard!

Black Hill Trail

Alright

September, 2021 by byronkwild

It was alright - the trail didn’t give much view of the lake itself and also didn’t circumnavigate it. You just kind of end up in a neighborhood. That said it was wide and well maintained and easy to navigate.

Cross County Trail (VA)

Disappointed

September, 2021 by interlake1395

Seems like a great path but horribly marked. I started at the Occoquan end and made it maybe five miles before getting frustrated and lost several times. There are intersecting trails, neighborhood paths, etc. that all look the same but no signage to tell you which way to go. Halfway through I started using this app for the trail map and still got off the trail several times.

Chesapeake & Ohio Canal National Historical Park

My first multi day ride

September, 2021 by kevin339

I completed this ride the first week of September, cycling from Cumberland to DC the day after Hurricane Ida passed through. The first time I have done a multi-day ride. Took the Amtrak to Cumberland with my bike and stayed at 9 Decatur (recommended). The trail was in good shape. A couple of additional puddles from the rain but very rideable. I had a great time. Four days and three nights. Rode 50/50/50 and 30 miles. Camping worked out very well at the hiker/biker sites. The only major hitch was the Pawpaw tunnel had just closed and taking a bike loaded with gear up and over is quite a slog. Hopefully some entrepreneurial locals have come up with some drive around alternatives. Unless you are a purist I recommend taking advantage if they have.
Don't expect stunning vistas but settle in to a rhythm and enjoy the history and it is a meditative and fulfilling experience.
Thanks to all the park staff who keep the park in such great shape.

Cub Run Stream Valley Trail

Trail Ride

September, 2021 by lvernon

This is a nice scenic shady trail, however it’s pretty overgrown in certain areas.

Fairfax County Parkway Trail

Signs Needed

September, 2021 by mlawrence301

Signs for riders to take caution or maybe even to STOP should be posted at the crosswalk located at Pinecrest Road overpass. Riders are can only see one direction depending on what way they are riding due to sound barriers. On coming traffic from East will only see them when they emerge from sound barriers.

Western Maryland Rail Trail

Nice Trail!

August, 2021 by wittychicatcs

My husband and I took this trail from Hancock, going west, for ~ 16 miles and then back again. We ride multi use bikes.
We thought this trail was great! It has convenient access points and plenty of parking w opportunities to “rest”.
The trail is flat so pedaling is required the entire time but it isn’t a difficult trail. We went in August, so there was plenty of shade from the full foliage.
The trail does have a couple rough spots where roots are pressing up on the pavement but they are not challenging or severe. It has lots of straight stretches, just as the railroad track it follows would’ve had. No surprise there. The bridges that merge the trail to the C & O canal tow path are in excellent condition! There are C &O points of interest to stop and check out and a campsite or two along the part we travelled. Saw a good bit of wildlife but nothing dangerous. While the full foliage blocks views of the Potomac most of the time, the trail is a feast for the other senses. Birdsong is plentiful and the smells of the river and mountain air are easily detected.
I’d recommend this trail to anyone looking for a bit of exercise ( really no coasting unless you’re on an e bike) and I suspect it is absolutely beautiful during the autumn too. No trail we’ve been on is absolutely perfect in every way, but we’ve never had to pay to go on one either, so doubt let the negative reviews of this one fool you.

Great Allegheny Passage

Very enjoyable

August, 2021 by carebare

Started in Cumberland and headed west. Complete glide back to Cumberland

Great Allegheny Passage

GAP ride

August, 2021 by kylemarsden

my son and i rode this trail over 3 days camping along the way at West Newton & Confluence. this trail is peaceful and quiet once out of Pittsburgh. The people in all the towns are social and glad to help in anyway needed. The trail has plenty of places to rest and relax. you follow rivers probably 120 of the 150 miles

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