Winchester, VA Cross Country Skiing Trails and Maps

462 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...

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...

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...

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...

Accordion

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...

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...

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...

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...

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...

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...

Accordion

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...

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...

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...

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...

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...

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...

Accordion

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...

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...

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...

Recent Trail Reviews

Chesapeake & Ohio Canal National Historical Park

C&O round trip

May, 2022 by andybeaire56

We did from Cumberland to DC then from DC back to Cumberland! August 2021 hot as hades in the high 90’s and thunderstorms! Had a blast! Camped the entire way except for 1 day at motel lol needed a shower! Awesome experience with a huge tunnel that we had to walk our bikes through like a mile ! Rode all over the DC area and visited many places ! DC is very bike friendly!

Great Allegheny Passage

Awesome Experience

May, 2022 by andybeaire56

My daughter and I did a round trip from Pittsburg to Cumberland! Then Cumberland back to Pittsburg! Camped and did motel. Just awesome! We have made a few extra trips driving from Mansfield, Ohio to Cumberland to just do the Cumberland to Eastern Continental Divide and back spend night in Cumberland and biked a few miles down the C&O and back before driving home!

Great Allegheny Passage

Nice trail - walk with dogs

March, 2022 by johnwybranowski

Trail was nice to walk our dogs; areas of full sun and shade.

Accordion

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

The west is best/brewery-connector trail

March, 2022 by bikeridesandbreweries

This is our home trail, so this ride was probably our 1,000th. Starting very close to Washington, DC in Arlington, VA, the 44-mile W&OD began with a series of short hills. For about five miles, we rode through wooded neighborhoods bordered by high retainer walls that shielded us from traffic on Route 66. There are a few intersections in the town of Falls Church, but the trail has recently been widened and a few pedestrian bridges have been added. There is almost always a significant amount of traffic on this trail; weekend rides can be frustrating slogs around families with strollers, dogwalkers and children testing their training wheels.
Vienna (with one brewery steps from the trail) was the next town we passed through as we followed the soft buzz of the overhead power lines. Over the years, more and more townhouse communities have sprung up alongside the trail, but still, we frequently see deer grazing fearlessly alongside the trail, and today, we saw a fat gopher, a rabbit, and a black snake.
Next, we pedaled through Reston and along Northern Virginia’s high-tech corridor. During this segment of the trail, we passed the first of three golf courses and two ice skating rinks. A few placid miles later, we crossed through the town of Herndon where one of several good bike shops abut the trail. Things began to look decidedly rural as the trail approached Ashburn, where it traversed broad open fields and passed by a huge stone quarry. The ride through Ashburn was pleasant and traffic definitely decreased the further west we rode, but the prettiest and most peaceful part of the trail began when we passed Leesburg. Leesburg is a very cute and historic town with several breweries, and outside of town, a number of fun wineries.
The remaining 13 miles of the trail were rolling and predominately shaded with occasional barns and farmhouses visible through the trees. Alongside the trail is a 32-mile crushed gravel equestrian trail, and it is on this end of the W&OD where the rare horseback rider is likely to be seen. The trail ends on the edge of the town of Purcellville, where there are restrooms, a bakery that sells bottles of water, a very good restaurant, and more good breweries. (Actually, there are 21 breweries within two blocks of the trail which has to be some kind of record!)

Great Allegheny Passage

Awesome trail

February, 2022 by berna

Rode the trail from Pittsburg to Cumberland. had a great time and the views were amazing. My wife and I are planning to hike a portion of the trail. If anyone has done this please let me know what part you hiked. we want to hike from Rockwood to Cumberland. Any advise or tips would be greatly appreciated.

Black Hill Trail

Great moderate trail

December, 2021 by annettebernat22

Have been recuperating from a broken ankle and started hiking to improve my strength and flexibility. Found this trail to be a good challenge as I build my stamina. Good asphalt service and some inclines. But overall a great workout. Wonderful views of the nearby lake. Must be spectacular in the spring and fall. Will definitely be doing this one again.

WV Route 9 Bike Path

Path ends right at the local prison/juvie center

December, 2021 by adammeche530

I love the path except that it just dumps you onto the should next to the detention center on the Martinsburg side.
Additionally you have to be on the side of the highway for several of the road crossings, it's good that you're not just riding the shoulder the whole time but during these crossings you face those risks.
Other than that it's a really nice path very smooth and of course you have the beautiful WV scenery

WV Route 9 Bike Path

Not my top choice

November, 2021 by darylmarlisa

This trail seems to have been designed by a highway engineer with not enough consultation with bikers or landscape architects or conservationists. Its essentially a bike highway, graded, paved and fenced just like the highway it runs right along. The land around the trail is aggressively mowed so there is no vegetation to support wildlife or provide shade for trail users. Very noisy from highway traffic which at times is only a few a few feet away. We won't be back.

Western Maryland Rail Trail

Perfect Fall Day

November, 2021 by moonstruckdragonlass

We picked the rail trail as our first venture back into biking after 5-6 years away. We started in Hancock and went west. The scenery was STUNNING and the ride was easy for us unseasoned riders.

From riding along a corn field with a backdrop of rolling hills in dazzling fall colors, to passing a cow field dotted with burnt out houses, to heading along a sheer drop off and between a narrow cut out in the rock, this route was absolutely stunning. I can't wait to head back and tackle another stretch (Or even the same one again!)

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.

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