Explore the best rated trails in Winchester, VA. Whether you're looking for an easy walking trail or a bike trail like the H & F Trolley Trail and Meadowlark Connector Trail. With more than 29 trails covering 4295 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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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 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 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 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 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...
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 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...
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 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,...
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...
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...
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....
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;...
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...
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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...
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...
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...
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...
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...
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...
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 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...
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...
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...
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...
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...
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 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...
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 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...
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...
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 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...
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 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 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...
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 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...
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...
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...
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 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...
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...
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 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,...
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...
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...
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...
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;...
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...
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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...
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...
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...
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 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...
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...
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 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...
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...
Rode this trail Friday October 4 took canal towpath west until the second bridge connection and continued until the pave trail ended. Towpath was nice and dry but rough ( should have worn gloves ) Went back on paved Western Maryland Rail Trail. There were 2 gigantic parking lots which had no cars not sure if they are necessary but nice. The trail has grown longer since the last time I was here.
First time at this trail. Went to Purcellville Saturday October 5 after riding Brunswick to Harpers Ferry. Lots of parking even for the big minivan. Heading East out of town the trail is smooth and flat following the power line right of way. Total ride was around 40 miles seemed easier going East. Many rest areas and food stops along my ride. Kind of cool but nice weather. Also 90 percent of the cars stopped to let me cross at the many intersections. Not used to this and strange ( I am from Ohio )
I use the trail in the Vienna area and am elderly and love to use the trail walking to exercise. There are some longer parts where there are no facilities (benches) to stop and rest. Could more benches be added please to aid those of us (the elderly) who love to walk the trail but are limited because we need to stop and rest more often. Thank you.
Love the trail, but surface could use a little TLC though, many gravely spots for folks with three wheels on the ground.
Brings back a lot of childhood memories, I was always riding my bike on this trial, started the trial in West Newton, PA!!!
I enjoyed this trail so much! I can say we road to the 12.5 mile marker and it was paved all the way through. There was slight elevation, but not enough to notice. There were signs all along the way talking about the Rail Line and also mile markers every mile. There are some decent bumps in the pavement from tree roots growing under the trail but not enough to deter riders but sure does hurt your bum if you're talking and not expecting it! All in all, a lovely paved trail and I would drive 2 hours all over again just to ride it! Fair warning, the bathrooms at the Big Pool trailhead are a little bit like walking into a gas station bathroom off the beaten path...but I survived!
Started at the north end and got ½ mile in before turning around. Large cobble stones, slick mud, large rocks, stair steps to bridge crossings and rocky water crossings are BAD news for road tires! Nobby mountain or gravel tires will have no problems. Don’t try without the right tired unless you want to ruin your bike crashing.
Excellent. Rode from Little Orleans to Hancock. Small area of gravel but mostly asphalt.
Rode from Cumberland to Frostburg and back. Uphill climb to Frostburg but reasonable, not strenuous. Easy downhill return to Cumberland. Excellent trail conditions. Beautiful scenery. One tunnel.
Just feel so fortunate to have this available to us.
I just finished the (GAP/C&O) trail this past weekend and all was good. The dry couple of weeks helped a lot. Some ruts and only a few puddles, which is to be expected. Nice to see some of the new upgrades along the trail. Make sure you take extra water during these months. Sometimes the pumps don’t work. Great to see the trail patrol cyclists out riding as well.
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