Explore the best rated trails in Winchester, VA. Whether you're looking for an easy walking trail or a bike trail like the Meadowlark Connector Trail and Fairfax County Parkway Trail. With more than 33 trails covering 4312 miles you’re bound to find a perfect trail for you. Click on any trail below to find trail descriptions, trail maps, photos, and reviews.
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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...
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...
Following the Potomac River, the C&O Canal Towpath traverses the Chesapeake & Ohio Canal National Historical Park for 184.5 miles be-tween Georgetown in Washington, D.C., and Cumberland, Maryland. For...
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...
Ever since the Great Allegheny Passage (GAP) was completed in 2013, overnight bicycle riders and backpackers have flocked to the 150-mile rail-trail that travels through Western Pennsylvania and...
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...
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...
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...
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...
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...
Hugging the picturesque Potomac River and the Chesapeake and Ohio Canal (C&O Canal Towpath), the Western Maryland Rail Trail (WMRT) rolls for nearly 28 miles through Maryland’s narrow panhandle wedged...
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...
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...
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The Washington and Old Dominion Trail (W&OD), one of suburban Washington, D.C.’s most popular rail-trails, is a fantastic link between the state’s rural and historical past and the nation’s capital....
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....
Named in honor of the late Ed Miller, a longtime caretaker at Renfrew Park & Museum and member of the Waynesboro Historical Society and Renfrew Institute, the Ed Miller Memorial Trail winds through...
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...
Running along N. East Street in Frederick, this very short segment of trail is built on a former rail corridor. There are plans to extend the trail along the former Walkerville Southern Railroad...
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...
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...
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...
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,...
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...
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....
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...
Ever since the Great Allegheny Passage (GAP) was completed in 2013, overnight bicycle riders and backpackers have flocked to the 150-mile rail-trail that travels through Western Pennsylvania and...
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...
Named in honor of the late Ed Miller, a longtime caretaker at Renfrew Park & Museum and member of the Waynesboro Historical Society and Renfrew Institute, the Ed Miller Memorial Trail winds through...
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...
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...
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...
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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...
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...
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...
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...
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...
Leading visitors through the final events of the Second Battle of Manassas in the Manassas National Battlefield Park, this trail is comprised of several connected loops with a number of short spur and...
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...
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...
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...
Hugging the picturesque Potomac River and the Chesapeake and Ohio Canal (C&O Canal Towpath), the Western Maryland Rail Trail (WMRT) rolls for nearly 28 miles through Maryland’s narrow panhandle wedged...
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...
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The Cross County Trail is a multi-use trail that generally follows the various stream valleys in Fairfax County, Virginia. It is officially named the Gerry Connolly Cross County Trail in recognition...
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...
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...
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;...
Ever since the Great Allegheny Passage (GAP) was completed in 2013, overnight bicycle riders and backpackers have flocked to the 150-mile rail-trail that travels through Western Pennsylvania and...
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,...
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...
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...
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...
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...
Leading visitors through the final events of the Second Battle of Manassas in the Manassas National Battlefield Park, this trail is comprised of several connected loops with a number of short spur and...
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...
Following the Potomac River, the C&O Canal Towpath traverses the Chesapeake & Ohio Canal National Historical Park for 184.5 miles be-tween Georgetown in Washington, D.C., and Cumberland, Maryland. For...
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...
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...
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...
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...
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...
Deep, sloshy, watery mud track; not even a trail. What a shame the National Park hasn’t improved this area. The GAP trail going northwest toward Pittsburgh is a dream to ride.
This is a must ride trail. Gravel path is well maintained, better than many asphalt trails I've been on in fact. Trees, rivers, waterfalls, butterflies, bridges 100ft+ above the canopy, if you enjoy nature, you can't miss this trail!
This is the best trail I have rode. Putts burgh to Cumberland md with many bridges and tunnels along the way. Great “patch towns” along the way. Connie to to cno canal and goes to dc
Rode from Pittsburgh to Cumberland. Great bridges and tunnels. Slight uphill until the continental divided. Then hold on for a few miles. Connects to cno which I did not do yet.
Great trail. Shaded for most of the route. Asphalt for all but two miles. The two miles goes around a spectacular tunnel that is closed for some reason. Very little cell service in little orleans which made it hard to find a he parking spot. The trail potentially could go over the Potomac to paw paw and connect to the cno. That has been scrapped for now. Most roots are Marked on the pavement which helps. You are on your own from Hancock to little orleans. Very remote.
All asphalt except for two miles that passes a tunnel that hopefully will be open some day. It would be nice if the abandoned bridges over the Latinos could be added someday and connect to the cno canal trail. Mostly shaded. Cool bars in Hancock md. You have to not to park in Hancock but no on the western end (little orleans). Zero cell device near there
A nice ride. The hub is a good place to start.
My husband and I rode from Homestead to Cumberland, with stops in Connelsville and Rockwood. Trail in excellent condition and adequate water stops. The slight upward grade going east on day 2 worth it, after Continental Divide on day 3 was all down hill. Took shuttle back to Pittsburgh, wish the train got in before 1130pm because that would have been a more economical option.
We took electric scooters and did 16miles of this trail was so beautiful seen 6 deer 5 turkeys will glad go back and explore more
Peaceful calm relatively long for your first trail but absolutely amazing couldn’t recommend more
Awesome trail. Nice scenery with history along the way. Only did point of rock to Brunswick. Stopped at the brewery. Next trip will be to Harpers Ferry.
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