Winchester, VA Cross Country Skiing Trails and Maps

378 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

26.8 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. Some sections are wheelchair/mobility scooter accessible but not all...
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
The Great American Rail-Trail highlights some of the country’s most iconic landmarks, well-known geography and storied history across a 3,700-miles-plus route between Washington and Washington....
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, Concrete
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 26.8 mi Asphalt

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Trails by activity

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...

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 American Rail-Trail

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

The Great American Rail-Trail highlights some of the country’s most iconic landmarks, well-known geography and storied history across a 3,700-miles-plus route between Washington and Washington....

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

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. Some sections are wheelchair/mobility scooter accessible but not all...

Western Maryland Rail Trail

MD - 26.8 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...

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 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

The Great American Rail-Trail highlights some of the country’s most iconic landmarks, well-known geography and storied history across a 3,700-miles-plus route between Washington and Washington....

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. Some sections are wheelchair/mobility scooter accessible but not all...

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...

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...

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 - 26.8 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...

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...

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...

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...

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...

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...

Accordion

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. Some sections are wheelchair/mobility scooter accessible but not all...

Western Maryland Rail Trail

MD - 26.8 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 American Rail-Trail

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

The Great American Rail-Trail highlights some of the country’s most iconic landmarks, well-known geography and storied history across a 3,700-miles-plus route between Washington and Washington....

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

Great Bike Trail!!!

September, 2019 by daysofourlives84

Brings back a lot of childhood memories, I was always riding my bike on this trial, started the trial in West Newton, PA!!!

Western Maryland Rail Trail

PAVED!

September, 2019 by tappindiva

I enjoyed this trail so much! I can say we road to the 12.5 mile marker and it was paved all the way through. There was slight elevation, but not enough to notice. There were signs all along the way talking about the Rail Line and also mile markers every mile. There are some decent bumps in the pavement from tree roots growing under the trail but not enough to deter riders but sure does hurt your bum if you're talking and not expecting it! All in all, a lovely paved trail and I would drive 2 hours all over again just to ride it! Fair warning, the bathrooms at the Big Pool trailhead are a little bit like walking into a gas station bathroom off the beaten path...but I survived!

Cross County Trail (VA)

Do not attempt with a road bike!

September, 2019 by terriannjma

Started at the north end and got ½ mile in before turning around. Large cobble stones, slick mud, large rocks, stair steps to bridge crossings and rocky water crossings are BAD news for road tires! Nobby mountain or gravel tires will have no problems. Don’t try without the right tired unless you want to ruin your bike crashing.

Accordion

Western Maryland Rail Trail

western MD rail trail

August, 2019 by rhon22jp

Excellent. Rode from Little Orleans to Hancock. Small area of gravel but mostly asphalt.

Great Allegheny Passage

GAP trail

August, 2019 by rhon22jp

Rode from Cumberland to Frostburg and back. Uphill climb to Frostburg but reasonable, not strenuous. Easy downhill return to Cumberland. Excellent trail conditions. Beautiful scenery. One tunnel.

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

Lucky Us

August, 2019 by sharonaevans00

Just feel so fortunate to have this available to us.

Chesapeake & Ohio Canal National Historical Park

Just finished!

August, 2019 by ah205

I just finished the (GAP/C&O) trail this past weekend and all was good. The dry couple of weeks helped a lot. Some ruts and only a few puddles, which is to be expected. Nice to see some of the new upgrades along the trail. Make sure you take extra water during these months. Sometimes the pumps don’t work. Great to see the trail patrol cyclists out riding as well.

Western Maryland Rail Trail

great ride

August, 2019 by llmoyers

It’s definitely a 5, but the mile marker is only up to 23. I enjoyed it very much. Especially viewing the mountains and going through them.

Great Allegheny Passage

This is the 4th we section of the GAP trail we've done. This time we started in Garret MD and rode to the continental divide. great ride. slight grade going to the divide but nice ride headed back. trail very well maintained..

August, 2019 by bpatch

This is the 4th we section of the GAP trail we've done. This time we started in Garret MD and rode to the continental divide. great ride. slight grade going to the divide but nice ride headed back. trail very well maintained..

Great Allegheny Passage

Bucket List

July, 2019 by ahaus

A definite on your bucket list! We rode the GAP/C&O from Pittsburgh to Georgetown. If you aren't a camper, the C&O requires thought and planning on where to stay. Riding both gives you a great perspective on different trails. When on the C&O, make sure you jump over to the Western Maryland Rail Trail for 22 miles, beautiful trail and a nice break from ruts and sticks (and turtles). Rode in late July, not many puddles.

Cub Run Stream Valley Trail

This trail is a danger to society

July, 2019 by tangierslane

The asphalt is broken every 4 feet with grass growing through it. It's only 4 feet wide. There are multiple steep slopes with little sight distance. Multiple locations with gravel out washes.

Bicyclists could not pass each other in opposite directions. Very large trees restrict bail-outs.

It has clear been abandoned by the FCPA.

Chesapeake & Ohio Canal National Historical Park

great trail needs maintenance badly in areas

July, 2019 by deborah.addy_tl

Rode the entire length a couple of times. Last time in June 2019. The first 10 miles out of Cumberland are terrible. If it has rained recently you will get muddy. When we went through it looked like they hadn't even mowed sections of it in a year. After that the trail had some rough patches but was ride-able. I would definitely not ride a rode bike on this trail, especially not with road tires. You need a bike with some suspension and some grip through this area. The Paw Paw tunnel was open when we went through, very interesting. Very rough and narrow inside the tunnel.
Don't know what you do if you meet a bicyclist coming the opposite direction inside the tunnel. Between Harper's Ferry and Brunswick they have resurfaced the trail and it was great. They need to put a ramp on the bridge to Harper's Ferry. We skip it as we don't want to leave our bikes behind and we aren't carrying fully loaded bikes up the spiral staircase. Fort Fredrick is an interesting side trip. The only reason the trail gets as a high a rating as I gave it is that there are free campsites all along the trail and historical markers. A lot of the campsites are by the Potomac river. They are very rustic just a picnic table, fire ring and Porta John. Sometimes there is a working water pump, sometime there isn't. I would suggest carrying a water filter, the water from the pumps is usually orange with iodine. They are usually quiet except for the occasional train. Along this trail you really can't get away from the occasional train. Also, bring bug spray in the summer if you are camping. You really don't need sunscreen, very seldom are you out from under the trees. There are huge trees all along the path.

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