Winchester Cross Country Skiing Trails and Maps

339 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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Activities
Length
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7 Results
Activities
Length
Surfaces
Type

Chesapeake & Ohio Canal National Historical Park

184.5 mi
State: DC, MD
Crushed Stone, Dirt, Gravel

Cross County Trail (VA)

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

Great Allegheny Passage

150 mi
State: MD, PA
Asphalt, Crushed Stone

H & F Trolley Trail

0.72 mi
State: MD
Asphalt

Warrenton Branch Greenway

2 mi
State: VA
Asphalt

Western Maryland Rail Trail

22 mi
State: MD
Asphalt
Trail Image Trail Name States Length Surface Rating
The Chesapeake & Ohio Canal National Historical Park (a.k.a. C&O Canal Towpath) follows the route of the Potomac River for 184.5 miles between Georgetown in Washington, D.C., and Cumberland, Maryland....
DC, MD 184.5 mi Crushed Stone, Dirt, Gravel
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
Now the longest rail-trail east of the Mississippi River, the 150-mile Great Allegheny Passage (GAP) spans two states in its course along great rivers and across mountain passes. Running from...
MD, PA 150 mi Asphalt, 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 22-mile paved route that will take you through several eras of American history. You can access this trail from...
MD 22 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...

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 - 22 miles

Plan a full day (or two) for your visit to the Western Maryland Rail Trail (WMRT), a 22-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 Allegheny Passage

MD,PA - 150 miles

Now the longest rail-trail east of the Mississippi River, the 150-mile Great Allegheny Passage (GAP) spans two states in its course along great rivers and across mountain passes. Running 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...

Chesapeake & Ohio Canal National Historical Park

DC,MD - 184.5 miles

The Chesapeake & Ohio Canal National Historical Park (a.k.a. C&O Canal Towpath) follows the route of the Potomac River for 184.5 miles between Georgetown in Washington, D.C., and Cumberland, Maryland....

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

Now the longest rail-trail east of the Mississippi River, the 150-mile Great Allegheny Passage (GAP) spans two states in its course along great rivers and across mountain passes. Running 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...

Chesapeake & Ohio Canal National Historical Park

DC,MD - 184.5 miles

The Chesapeake & Ohio Canal National Historical Park (a.k.a. C&O Canal Towpath) follows the route of the Potomac River for 184.5 miles between Georgetown in Washington, D.C., and Cumberland, Maryland....

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...

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 - 22 miles

Plan a full day (or two) for your visit to the Western Maryland Rail Trail (WMRT), a 22-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...

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...

Great Allegheny Passage

MD,PA - 150 miles

Now the longest rail-trail east of the Mississippi River, the 150-mile Great Allegheny Passage (GAP) spans two states in its course along great rivers and across mountain passes. Running from...

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...

Chesapeake & Ohio Canal National Historical Park

DC,MD - 184.5 miles

The Chesapeake & Ohio Canal National Historical Park (a.k.a. C&O Canal Towpath) follows the route of the Potomac River for 184.5 miles between Georgetown in Washington, D.C., and Cumberland, Maryland....

Western Maryland Rail Trail

MD - 22 miles

Plan a full day (or two) for your visit to the Western Maryland Rail Trail (WMRT), a 22-mile paved route that will take you through several eras of American history. You can access this trail from...

Recent Trail Reviews

Warrenton Branch Greenway

Great community asset!

May, 2018 by laurastark

The Warrenton Branch Greenway is a beautiful little connector trail. On a Tuesday morning, we saw folks out biking, jogging, and walking their dogs. During our early May visit, the trail was shady and green with lots of flowering bushes alongside. At the downtown Warrenton trailhead, we were also greeted by a little red caboose, which was cool to see. There were a couple of street crossings on quiet residential roads, but they were well marked and the drivers were courteous and happy to stop and let us cross.

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

Nice trail! Well paved & marked.

May, 2018 by opstadp

Rode part of this trail from Purcellville to Leesburg. We were short on time so only got to ride 7 miles out and 7 miles back. Loved the trail. Quiet, nicely paved, marked well and rural when you start out at the Purcellville end. Hope to go back and ride another section again and eventually cover all of it after a few rides!

Western Maryland Rail Trail

clean, paved trail with a little bit of history.

April, 2018 by amosonu

I rode from the trail head in Big Pool, MD to the fruit market about 8 miles away on Thursday, 4/26/18. It was a sunny day, 65°. I rode through a sparsely populated area and then paralleled the C&O canal for the rest of the way. The foliage is not in bloom yet so it is not so much a joyous experience as a healthy ride in cool weather. There was a road biker taking advantage of the paved asphalt surface riding at a fast clip. There were also a few other riders on comfort bikes enjoying the scenery like myself. I would recommend this trail to anyone who is tired of crushed gravel surface rail trails but still want that rail-trail feel. This trail parallels I-70 so it is a bit noisy. For this reason I give it only three stars.

Accordion

Cross County Trail (VA)

Not for Road Bikes

April, 2018 by dgoosbey2

I wish I read the reviews before taking my road bike on this trail. I started at the Lorton entrance and the trail quickly became mud and gravel. My road slick tires were definitely ill equipped for this segment of the trail. Better for cyclocross and mountain bikes.

Western Maryland Rail Trail

One of my favorites

February, 2018 by beckyaboardsvanteris

We love this trail and wouldn't mind riding it again someday. We had to travel to get to it so we stayed at a hotel in Hancock, MD so that we could ride the western half one day and the eastern half the next. I can't say I would recommend the America's Best Value Inn. We travel with a camper now, thank goodness. But the trail was just lovely and I recommend it.

Great Allegheny Passage

Allegheny/ CO Labor Day

December, 2017 by mmblhb

I rode the GAP /CO this past Labor Day weekend- best bike trip ever. 120 miles from Pittsburgh to Meyersdale (120 miles). Almost flat- never any sense of climbing, smooth trail on a road bike with 32mm tires and fenders. The ride from Meyersdale to Cumberland was easy- downhill the last 30 miles or so. Thanks to all the groups that put the trail together- what an asset to the region.

Great Allegheny Passage

Can't wait to do this again!

October, 2017 by aeboe

Rented bikes from Cumberland Connection (they were AWESOME!). We didn't get on the trail till 4:30 and made it to Gunter Hotel in Frostburg by sunset at 6:29. It is a lot of uphill walking from the trail to downtown Frostburg. Ask for room with new beds at Gunter and make sure and go to the mens bathroom to see the 'jail cell'. Ate at Shift which was amazing! We were on the trail by 8:40am, lunch at Rockwood (Rockwood Mills-the dessert were amazing!) by 12:30 and made it to Confluence by 3:30 for our shuttle pick up . We stopped many, many times for pictures! I hardly wanted to blink because this was such an amazing, beautiful experience!

WV Route 9 Bike Path

We Loved It!

October, 2017 by hummelr

We got a wonderful work-out on this trail, but the hills were not overly difficult. we biked late afternoon/evening in October. We started on the Martinsburg end, which is definitely hillier that the east end. We stopped for coffee at the Black Dog on the way back. It was a perfect stopping place, with nice bathrooms.

Great Allegheny Passage

serene and calm

October, 2017 by bicycle67

Great trail for multi-day ride with motels or camping, or single day rides. I had to find parking locations in order to ride several days, with Round trip rides of 40-60 miles/day (20-30 each way). A few confusing spots and a couple steep spots. Quite confusing in Pittsburgh, where markings are absent, and trail goes through the city streets, but lovely to arrive at Point State Park fountain. Cedar Creek Park especially lovely area, with camping (but gates lock at sundown so don't park late). Great long ride down gentle hill from Deal, MD (highest point on trail) to Cumberland. Long uphill ride back up 26 miles from Cumberland back to Deal. Beautiful trail.

WV Route 9 Bike Path

Far from peaceful

September, 2017 by scott_music

From hundreds of cars to the overhead planes landing at a nearby airport, this trail was full of urban noise. The challenging hills, the asphalt trail and the geocaches were a plus but, for me, prefer a trail more serene.

Western Maryland Rail Trail

Just far enough from the cities!

September, 2017 by rmjonesjr

This wonderful trail is just far enough from the heavily populated Baltimore/Washington area that it is never crowded. Even on "busy" weekends you'll pass just a few other friendly folks who enjoy biking enough to make the trek to Hancock. For us "weird" recumbent trike riders there are a few teeth rattling tree roots pushing up the asphalt in places. Regular bikes with even modest suspension or fat tires will barely notice them. Enjoy this wonderful gem of a trail!

WV Route 9 Bike Path

omega3jane

September, 2017 by omega3jane

I have ridden this path several times. There are many hills and some come straight down to a stop to cross the road. After which, you then pedal straight up hill. However, the path is quite do-able. There are two treats for you on this ride - 1) a stop at Black Dog Coffee and at the Martinsburg end, you can cross the highway (carefully) to find the Berkeley County Human Society and visit with the pooches! Enjoy and cycle safe!

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