Winchester, VA Cross Country Skiing Trails and Maps

422 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

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...

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...

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

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

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...

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 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...

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...

Accordion

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....

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 - 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...

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...

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...

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

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...

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...

Recent Trail Reviews

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.

Unfinished Railroad Loop Trail

Nice length for kids

October, 2020 by margaret.mcqueen

This is an easy trail for kids. They learn a little history and have fun. One of my kids danced on most of it. The loop is a good feature.

Accordion

Black Hill Trail

beautiful in the fall

October, 2020 by jgeltmac

Very scenic route, paved bike path. We went on a Sunday after 2pm and it wasn’t crazy packed. It is true that there are a bunch of hills so be prepared for a workout. Definitely worth a try.

Chesapeake & Ohio Canal National Historical Park

We did about twelve miles of the western part. Really pretty. We will be back!

October, 2020 by dannice

We did about twelve miles of the western part. Really pretty. We will be back!

Cross County Trail (VA)

awesome ride! just consider fatties

September, 2020 by keyjamesd

This is a mid-level bike trail with plenty of off trail single tracking. Most of the path is paved. There are some rough areas which is why I say, mid-level. Your gonna carry your $3000 road bike. I would have been very happy on my gravel bike, but I chose my fixed gear road bike. I know! I didn’t read reviews, and I’m kicking myself for it! But I still had an awesome time carrying some of the way.

Great Allegheny Passage

Fantastic Adventure

September, 2020 by ron.ritter

On June 30, 2020, I started in Cumberland at first light. Bike was fully loaded for a self sufficient adventure. I was on a carbon road bike with 23mm tires. There were only a couple sections where the gravel was soft an pillowy slowing me down a bit to ensure I stayed upright. The key to getting through this brief section is to keep pedaling. The more you pedal the more your bike wants to stay upright. Beyond that the the trail is very isolated in sections. At some parks/ parking lots along the route There are tool stations with air pumps. There are bathrooms along the that I thought were few and far between, perhaps due to Covid and some being removed. I was able to do 122 miles in one day fully loaded at about 13 mph, just interested to see how far I could go. I noticed most others were not moving at that speed. I made the return trip back to Cumberland the next day.

H & F Trolley Trail

Wonderful starter trail

September, 2020 by 36s7x5nqjp

Took my granddaughters to this trail today. One is younger and a new cyclist (training wheels off this past summer). The other a bit older but had not been biking in a while. Very smooth paved trail. Several small bridges to go over and waterways right off the trail. Nice landscaping done by several local businesses. A good amount of benches to take a break on. Glad we found this gem.

Braddock Road Sidepath

Needs to be resurfaced

August, 2020 by graham.hay1893

There are a lot of hazards on this trail that make using it unpleasant.

Winchester Green Circle

Beautiful!

August, 2020 by oliviaives698

This trail is beautiful. You walk and see the colorful wildflowers, birds and can hear the cows splashing in the near by ponds. If your lucky you can stand on the bridge and watch the train go by. These simple pleasures in life might not be for everyone, but for me...I enjoy and appreciate the natural beauty of this trail. Yes, there is a part where you walk by the roads, SO WHAT....This trail is safe, well maintained and LEVEL.

Braddock Road Sidepath

Braddock Road Sidepath

August, 2020 by kapoej

This is a paved trail that runs along a very busy road. I personally use it for working out through running and road biking. Often there are very few fellow users of this path. It is not very scenic route so I recommend it for those purely looking to feel the joy of working out, wanting little to no fellow runners or bikers, and just wanting long paved straightaways.

WV Route 9 Bike Path

Challenging but well-kept trail

August, 2020 by jwlald_tl

I love this route in part because I grew up in C.T. Hills on northwest end are a great workout. Trail is in excellent shape; no detours. Parking available at both ends. Wear sunscreen because there’s no shade, take plenty of water because there’s no fountains, and be conscious that there are no public toilets on the route.

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