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Winchester, Virginia (VA) Trails & Maps

Looking for the best trails around Winchester, Virginia? Find the top rated trails in Winchester, whether you're looking an easy walking path or a long bike trail, you'll find what you're looking for. Click on a trail below to find trail descriptions, trail maps, photos, and reviews.
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TRAIL LENGTH SURFACE TRAIL MAP

Black Hill Trail

4.3 miles
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 the middle is unpaved and rocky. A good ...
Asphalt
Dirt

Braddock Road Sidepath

10 miles
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 provides connections to George Mason University's ...
Asphalt
Concrete

Carpendale Trail

1 miles
Short new trail connecting Ridgeley, WV with the C&O Canal Towpath at milepost 183 near the east end of Cumberland, Maryland. This new trail will include the Knobbley Tunnel and Bridge over the Potomac River.
Crushed Stone

Centreville Road Sidepath

4.7 miles
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 from just south of the Dulles Toll Road/SR ...
Asphalt

Chesapeake & Ohio Canal National Historical Park

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. Hundreds of original features, including ...
Crushed Stone
Dirt
Gravel

Cross County Trail (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 sections. Some sections are suitable for horseback ...
Asphalt
Ballast
Concrete
Crushed Stone
Dirt
Gravel

Fairfax County Parkway Trail

28.3 miles
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 is usable for walking, biking and inline skating. ...
Asphalt

Great Allegheny Passage

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 Pittsburgh, Pennsylvania, to Cumberland, Maryland, ...
Asphalt
Crushed Stone

Harpers Ferry Railroad Bridge

0.14 miles
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 between Harpers Ferry and the Chesapeake & Ohio ...
Boardwalk

Herndon Parkway Sidepath

2 miles
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 most street intersections. The trail also connects ...
Concrete

Linton Hall Road Trail

5.4 miles
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 local residents of the communities lining the ...
Asphalt

Lord Fairfax Community College Connector Trail

0.3 miles
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 Warrenton Branch Greenway will connect to ...
Crushed Stone

Lovettsville Shared-Use Path (Route 287)

1.13 miles
From the Town of Lovettsville, VA web site: Pedestrian/Bike Path on 287 VDOT awarded Highway Enhancement Grant Funds to the Town to develop a Pedestrian/Bike Path along 287 through the Town of Lovettsville. Loudoun County Gas Tax money ...

Meadowlark Connector Trail

1.25 miles
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; trail-goers can then take the longer trail southeast ...
Asphalt

Pike 2 Bike Trail

8.5 miles
This corridor is an 8+ mile section of abandoned Pennsylvania Turnpike (built and never used) and is currently owned by the Southern Alleghenies Conservancy (http://sac-sarcd.org/sac_info.htm). The "trail" is officially closed for liability ...
Concrete

Seneca Creek Greenway Trail

22.1 miles
Seneca Creek Greenway Trail was built by a coalition of organizations and follows the meandering Seneca Creek near Germantown, MD, from the Potomac River to State Route 355 (Frederick Road). NOTE: Only parts of the trail are multi-use; horses ...
Dirt

Stringfellow Road Sidepath

3 miles
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 amenities, such as Chantilly High School and ...
Asphalt
Concrete

Sudley Manor Drive Trail

4.3 miles
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 and Bull Run, and acts as a recreation and ...
Asphalt

Unfinished Railroad Loop Trail

1.2 miles
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 Gap Railroad’s main line, which linked Manassas ...
Dirt

WV Route 9 Bike Path

10 miles
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 of the trail is fairly flat, the northern ...
Asphalt

Warrenton Branch Greenway

1.5 miles
The Warrenton Branch Greenway follows a segment of the old Warrenton Branch Spur railroad, running 1.5 miles between the trailhead behind the restaurant at the depot in downtown Warrenton (4th St. near Lee St.) and Castle Kingston Lane just ...
Asphalt

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

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 fantastic link between Virginia's rural and historical ...
Asphalt
Concrete

West Ox Road Sidepath

2.9 miles
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 Fairfax), providing a link to numerous neighborhoods ...
Asphalt

Western Maryland Rail Trail

22 miles
Plan a full day (or two) for your visit to the Western Maryland Rail Trail, a 22-mile paved route that will take you through several eras of American history. You can access this trail from many points, but the main trailhead is in the quaint ...
Asphalt

White's Mill Trail

1.3 miles
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 viewing along the path.
Asphalt