Winchester, VA Hiking Trails and Maps

447 Reviews

Looking for the best Hiking trails around Winchester?

Find the top rated hiking trails in Winchester, whether you're looking for an easy short hiking trail or a long hiking trail, you'll find what you're looking for. Click on a hiking trail below to find trail descriptions, trail maps, photos, and reviews.

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Activities
Length
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Type
30 Results
Activities
Length
Surfaces
Type

Black Hill Trail

4.3 mi
State: MD
Asphalt, Dirt

Braddock Road Sidepath

10 mi
State: VA
Asphalt, Concrete

Carpendale Trail

0.8 mi
State: MD, WV
Crushed Stone

Centreville Road Sidepath

4.7 mi
State: VA
Asphalt

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

Cub Run Stream Valley Trail

9.1 mi
State: VA
Asphalt

Fairfax County Parkway Trail

28.3 mi
State: VA
Asphalt

Folly Lick Branch Trail

2 mi
State: VA
Asphalt

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

Harpers Ferry Railroad Bridge

0.14 mi
State: MD, WV
Boardwalk

Hawksbill Greenway

2 mi
State: VA
Asphalt

Herndon Parkway Sidepath

2 mi
State: VA
Concrete

Linton Hall Road Trail

5.4 mi
State: VA
Asphalt

Meadowlark Connector Trail

1.25 mi
State: VA
Asphalt

Powerline Trail (MD)

6 mi
State: MD
Dirt, Grass

Rocky Run Stream Valley Trail

4.6 mi
State: VA
Asphalt, Crushed Stone
Accordion

Stringfellow Road Sidepath

3 mi
State: VA
Asphalt, Concrete

Sudley Manor Drive Trail

4.3 mi
State: VA
Asphalt

Unfinished Railroad Loop Trail

1.2 mi
State: VA
Dirt

WV Route 9 Bike Path

10 mi
State: WV
Asphalt

Warrenton Branch Greenway

2 mi
State: VA
Asphalt

West Ox Road Sidepath

2.9 mi
State: VA
Asphalt

Western Maryland Rail Trail

27.5 mi
State: MD
Asphalt

White's Mill Trail

1.3 mi
State: VA
Asphalt

Winchester Green Circle

5.3 mi
State: VA
Asphalt
Trail Image Trail Name States Length Surface Rating
Black Hill Trail offers a wooded trek with gentle inclines through Black Hill Regional Park in Boyds, Maryland, just outside of Washington, DC. The trail is primarily paved, though a short section in...
MD 4.3 mi Asphalt, Dirt
The Braddock Road Sidepath parallels Braddock Road and New Braddock Road (State Route 620) between Centreville and Burke, two bedroom communities in Northern Virginia's Fairfax County. The trail...
VA 10 mi Asphalt, Concrete
The Carpendale Trail straddles the North Branch of the Potomac River between Carpendale in West Virginia and Cumberland in Maryland. The wooden bridge spanning 386 feet across the river is a...
MD, WV 0.8 mi Crushed Stone
This paved sidepath runs parallel to Centreville Road/State Route 657, providing a safe route for alternative transportation along the busy suburban roadway in western Fairfax County. The trail runs...
VA 4.7 mi Asphalt
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 Cub Run Stream Valley Trail offers a paved route meandering through Cub Run Stream Valley Park in the Northern Virginia suburb of Centreville. Though it's surrounded by residential neighborhoods,...
VA 9.1 mi Asphalt
The Fairfax County Parkway Trail parallels Fairfax County Parkway/State Route 286 on its route across Fairfax County, Virginia. While the paved trail varies in width and condition, most of the trail...
VA 28.3 mi Asphalt
The Folly Lick Branch Trail begins in Herndon, a northern Virginia suburb. The paved pathway begins off Herndon Parkway and winds northeast along the Folly Lick Branch stream through a residential...
VA 2 mi Asphalt
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
This rail-with-trail bridge crosses the Potomac River near its confluence with the Shenandoah River, at Harpers Ferry, West Virginia. A cantilevered section of the bridge allows pedestrian access...
MD, WV 0.14 mi Boardwalk
The Hawksbill Greenway is a 2-mile non-motorized pathway in the town of Luray, Virginia, two hours from Washington D.C. It extends from Linden Street in the west to the Flowering Forest in the east....
VA 2 mi Asphalt
This short sidepath parallels Herndon Parkway on the eastern edge of Herndon in Northern Virginia. Much of the trail is the width of a standard sidewalk, and it includes crosswalks and curb-cuts at...
VA 2 mi Concrete
The Linton Hall Road Trail runs parallel to its namesake—also signed as State Route 619—in western Prince William County. More utilitarian than scenic, the trail acts as a transportation route for...
VA 5.4 mi Asphalt
Opened in 2009, the short Lord Fairfax Community College Connector Trail extends from the parking lot of the junior college to its temporary endpoint in a scenic wildlife area. Eventually, an extended...
VA 0.3 mi Crushed Stone
Although less than two miles long, the Meadowlark Connector Trail provides a terrific link between the Meadowlark Botanical Gardens and the popular W&OD Trail. The trail meets the W&OD in Vienna;...
VA 1.25 mi Asphalt
This trail traces a hilly green swath located in a Pepco electric utility right-of-way that stretches between South Gernmantown Recreational Park and Muddy Branch Stream Valley Park. It's a natural...
MD 6 mi Dirt, Grass
Rocky Run Stream Valley Trail is part of the countywide trail system. This trail runs from the Fairfax County Parkway to Ellanor C. Lawrence Park. The distance along the trail from the Parkway to the...
VA 4.6 mi Asphalt, Crushed Stone
Accordion
The Stringfellow Road Sidepath runs for three miles through Chantilly and Centreville in Northern Virginia's Fairfax County. The asphalt and concrete trail connects multiple neighborhoods to various...
VA 3 mi Asphalt, Concrete
The Sudley Manor Drive Trail runs parallel to the southern 4.5 miles of its namesake road in western Prince William County. The trail services a number of the surrounding communities, such as Bristow...
VA 4.3 mi Asphalt
The Unfinished Railroad Loop Trail is a short hiking trail within Manassas National Battlefield Park. The rail-trail runs on a corridor planned in the mid-19th century as a complement to the Manassas...
VA 1.2 mi Dirt
The WV Route 9 Bike Path follows the busy thoroughfare from Martinsburg to the Charles Town/Ranson area. Note that the path runs through open space with little to no shade. While the southern portion...
WV 10 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
The West Ox Road Sidepath is a short paved trail along the west side of West Ox Road. The trail extends from the Oak Hill area of Fairfax County to southeastern Chantilly (near Fair Oaks Mall in...
VA 2.9 mi Asphalt
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
The White’s Mill Trail provides a scenic route through wetlands and residential areas in the rural town of Warrenton. Trail-goers will enjoy the natural beauty of the Cedar Run valley and wildlife...
VA 1.3 mi Asphalt
Like its name suggests, this is a circular pedestrian and bike trail in Winchester, Virginia. A popular trail, the trails appeal lies not just in its lovely landscaping, or simply as a welcoming space...
VA 5.3 mi Asphalt

Now, More Than Ever, Trails Matter!

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Trails by activity

Recent Trail Reviews

Chesapeake & Ohio Canal National Historical Park

My first multi day ride

September, 2021 by kevin339

I completed this ride the first week of September, cycling from Cumberland to DC the day after Hurricane Ida passed through. The first time I have done a multi-day ride. Took the Amtrak to Cumberland with my bike and stayed at 9 Decatur (recommended). The trail was in good shape. A couple of additional puddles from the rain but very rideable. I had a great time. Four days and three nights. Rode 50/50/50 and 30 miles. Camping worked out very well at the hiker/biker sites. The only major hitch was the Pawpaw tunnel had just closed and taking a bike loaded with gear up and over is quite a slog. Hopefully some entrepreneurial locals have come up with some drive around alternatives. Unless you are a purist I recommend taking advantage if they have.
Don't expect stunning vistas but settle in to a rhythm and enjoy the history and it is a meditative and fulfilling experience.
Thanks to all the park staff who keep the park in such great shape.

Cub Run Stream Valley Trail

Trail Ride

September, 2021 by lvernon

This is a nice scenic shady trail, however it’s pretty overgrown in certain areas.

Fairfax County Parkway Trail

Signs Needed

September, 2021 by mlawrence301

Signs for riders to take caution or maybe even to STOP should be posted at the crosswalk located at Pinecrest Road overpass. Riders are can only see one direction depending on what way they are riding due to sound barriers. On coming traffic from East will only see them when they emerge from sound barriers.

Accordion

Western Maryland Rail Trail

Nice Trail!

August, 2021 by wittychicatcs

My husband and I took this trail from Hancock, going west, for ~ 16 miles and then back again. We ride multi use bikes.
We thought this trail was great! It has convenient access points and plenty of parking w opportunities to “rest”.
The trail is flat so pedaling is required the entire time but it isn’t a difficult trail. We went in August, so there was plenty of shade from the full foliage.
The trail does have a couple rough spots where roots are pressing up on the pavement but they are not challenging or severe. It has lots of straight stretches, just as the railroad track it follows would’ve had. No surprise there. The bridges that merge the trail to the C & O canal tow path are in excellent condition! There are C &O points of interest to stop and check out and a campsite or two along the part we travelled. Saw a good bit of wildlife but nothing dangerous. While the full foliage blocks views of the Potomac most of the time, the trail is a feast for the other senses. Birdsong is plentiful and the smells of the river and mountain air are easily detected.
I’d recommend this trail to anyone looking for a bit of exercise ( really no coasting unless you’re on an e bike) and I suspect it is absolutely beautiful during the autumn too. No trail we’ve been on is absolutely perfect in every way, but we’ve never had to pay to go on one either, so doubt let the negative reviews of this one fool you.

Great Allegheny Passage

Very enjoyable

August, 2021 by carebare

Started in Cumberland and headed west. Complete glide back to Cumberland

Great Allegheny Passage

GAP ride

August, 2021 by kylemarsden

my son and i rode this trail over 3 days camping along the way at West Newton & Confluence. this trail is peaceful and quiet once out of Pittsburgh. The people in all the towns are social and glad to help in anyway needed. The trail has plenty of places to rest and relax. you follow rivers probably 120 of the 150 miles

Great Allegheny Passage

Rode from Frostburg to Meyersdale

July, 2021 by garyv.email

My wife and I rode this portion of the trail on our recumbent tandem in June. It has been on of our favorites. The climb from Frostburg to the eastern continental divide was not too bad. It was great fun on the way down. ;-). The tunnels and the views are the big highlights. It was so cool how the lights came on as we rode through Borden tunnel. The cicadas were out in force as we rode through the woods. The Mason Dixon line is a great photo stop. We highly recommend the trail and will be back to ride more.

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

Busy in east, beautiful in west

July, 2021 by d.smithva

The W&OD is a great bike trail throughout, obviously. But the western part, generally from Herndon to Purcellville, is far nicer and less busy than the eastern part in the northern VA suburbs. The eastern part is my home trail and nice for a quick workout ride, but it is super busy with walkers, talkers, dog on long leashes and obnoxious dudes who think they are in the Tour de France. I like a nice fast ride as much as anyone, but the western portion is not choked with users, much more greenery in a rural-exurban setting, far more beautiful and one that evokes the railroad of yore more, too. Leesburg and Purcellville offer nice rest/eat/drink/chill options if you desire that. Bike from Herndon to Purcellville, the trip back is somewhat more downhill and makes it *slightly* more uphill west and downhill on the return, a nice recipe. It's about 13 miles in that stretch, 26 RT. 4 stars for the eastern bit (after all, a nicely maintained road bike path), 5 stars for western section (as nice as any road bike rail trail, and well paved).

Western Maryland Rail Trail

We spent the day biking from Hancock west on the paved trail. Wonderfully maintained. Loved the scenery and although it was warm we had a terrific time.

July, 2021 by rhanson2008

We spent the day biking from Hancock west on the paved trail. Wonderfully maintained. Loved the scenery and although it was warm we had a terrific time.

Cross County Trail (VA)

great community trail, but could use updated markings

July, 2021 by fredbenson

Last July I walked the north half of this trail (top 20 miles) and today I walked the bottom half (bottom 20 miles). Both halves were beautiful, though I think I’d give a slight edge to the northern half in terms of beauty and general enjoyment. When I walked the northern half last year, I relied solely on the maps provided by fairfax county, which are black and white and not particularly detailed. Since I made it through the hike, they obviously got the job done, but not without a lot of backtracking and hunting for trail markers. The southern half would have been just as bad, if not worse, if I hadn’t found this app last night before I left this morning. For any others considering traversing the entire county by foot-whether in two trips or more-this app will save you from a huge amount of backtracking and stress thinking you have left the trail. Overall, it was a great hike though!

Great Allegheny Passage

great trail

July, 2021 by ghmason1

It’s a great trail. Been riding it since the beginning. The elitists need to tone it down though. People like to enjoy the scenery and shouldn’t have to worry about getting ran into or yelled at by the Strava segment obsessors.

Great Allegheny Passage

Beautiful with camping, lodging, food, water fun!

June, 2021 by rick1635

What a great trail of crushed limestone…great climb up from Cumberland at 660’ to about 2,600’ at the Eastern Continental Divide, then a slow decline the rest of the way to Pittsburgh. Great B&B’s along the way in Meyersdale, Rockwood, Confluence…Ohiopyle State Park is one of a few terrific places to stay for the night and take a day off for whitewater rafting. Also take a moment for a bit of hiking or even a trip to see Falling Waters, a Frank Lloyd Wright home built on a waterfall. Only went as far as West Newton this time around but will be back to do it again. Many also start at Pittsburgh and finish at Cumberland enjoying a 24 mile downhill ride into town. Many choices for food and shelter.

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