Winchester, VA Cross Country Skiing Trails and Maps

432 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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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. 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 27.5 mi Asphalt

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Trails by activity

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...

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

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

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....

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...

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....

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...

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...

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...

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...

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....

Accordion

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

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...

Recent Trail Reviews

Centreville Road Sidepath

Centerville Side Path

May, 2021 by vdwyswvhyf

This path is really more of just an asphalt sidewalk. It is very close to a heavy traffic road

Chesapeake & Ohio Canal National Historical Park

great ride

May, 2021 by james.pirtle

Nice trail, easy. worth the drive

Chesapeake & Ohio Canal National Historical Park

A great experience for an afternoon or for a whole weekend!

April, 2021 by cyschill98

My wife and I enjoy this well-maintained trail almost every weekend when the weather is nice. We like to drop onto the trail at different points along its 180+ mile length for variety—it’s absolutely beautiful with nature around every turn, mixed with lots of history. We recommend heading down to the Potomac River on one of the many paths to enjoy the scenery when you need a break.

Accordion

Chesapeake & Ohio Canal National Historical Park

east of Brunswick on C n O

April, 2021 by soucy.henri

Rode the trail from Harpers Ferry to Locke 8 on Tuesday, April 13th. Be aware that just east of Brunswick is a detour that crosses an ancillary canal that proved to be impassable and resulted in a 10-mile plus to detour, over road with little shoulder and hilly. Another cyclist said the area was passable as recently as the Sunday prior (4/11).

Great Allegheny Passage

Beautifully Maintained

March, 2021 by mjr9201

I rode the GAP late last Fall from Cumberland to Pittsburgh and enjoyed it immensely. Did Cumberland to Connellsville Day 1 and that was a little bit too long a day for me but the weather was great and I met up with some very cool people traveling in my direction. I did Connellsville to Pittsburgh relatively quickly on Day 2, arriving at Point State Park by midday. Lovely ride. Well maintained rail trail. Nice amenities all along the way. Beautiful scenery. Got lost a bit in McKeesport but found my way back relatively easily. Highly recommended. Now to go from Pittsburgh to DC!

Great American Rail-Trail

best trail ever

March, 2021 by tpassarelli_tl

wonderful trip across America

Cross County Trail (VA)

Great in sections

January, 2021 by elizabeth.scuderi

I ride this trail regularly. First of all you must have a hybrid, gravel or mountain bike to traverse several sections of gravel. My favorite section is between West Springfield and Route 50 because you pass by beautiful Lake Accotink.

Rocky Run Stream Valley Trail

lovely trail in the midst of city!

January, 2021 by asha

Beautiful trail amongst the woods and along the stream.

Chesapeake & Ohio Canal National Historical Park

Dargan Bend to Shepherdstown - silky smooth!

November, 2020 by themfoxes

This was my first ride on the C & O in years. I've stayed away due to rough gravel, pot holes, and rocks that even my hybrid couldn't overcome. But recently I heard that there had been resurfacing at Shepherdstown. What a world of difference! Crushed limestone that is compacted into a very level trail. We rode north from Dargan Bend to a couple miles past Shepherdstown. Dargan Bend was the closest parking lot we could find across from Harper's Ferry. Being there in late fall, the trees were bare but the river views were great. The trail north of Shepherdstown is gravel with rocks protruding here and there, making for a rough ride. We only traveled until hitting 10 miles from our start before turning back. Our timing couldn't have been worse as there was some kind of a foot race going on, but since we traveled 100 miles to get here we rode anyway. (I checked the NPS.gov website before going but saw no mention of the race, so not sure how one finds out about events on the towpath.) Overall, though, it was a great 20 mile ride.

Unfinished Railroad Loop Trail

Short and sweet walking trail.

November, 2020 by asha

Nice short trail. Good signs and not crowded.

Braddock Road Sidepath

Broken and dangerous

October, 2020 by instaurare

Use caution when on a bike. Keep a low speed. While they seem to be making some improvements slowly, in spots the pavement is so broken up it’s nearly impassible. Additionally the side path dumps you off on to the mail road without a clear way how to connection and it doesn’t even exist for a couple of important blocks.

Chesapeake & Ohio Canal National Historical Park

ride from Point of Rocks to Shepherdstown

October, 2020 by suzn_s

On 10/22/20 my friend and I rode the above stretch. It was absolutely beautiful! We were cautious due to the mornings heavy fog and all the damp leaves on the ground. Made the paths edges somewhat difficult to see. The trail was extremely smooth until you get to the Brunswick Waste Treatment Plant, where you share the dusty and bumpy road with big trucks coming and going from the plant. Pot holes were terrible there. But once back on the trail, it was a smooth sail. I believe it was around a 28-mile ride for us.

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