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 4296 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 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...
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 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...
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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...
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 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...
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...
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 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 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...
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;...
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 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....
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 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 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...
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 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 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...
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 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...
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...
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...
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...
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...
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 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...
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;...
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...
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 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....
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 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 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 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 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...
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...
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 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 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...
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...
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...
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 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 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 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...
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 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...
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 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...
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....
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 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....
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...
I rode the GAP late last Fall from Cumberland to Pittsburgh and enjoyed it immensely. Did Cumberland to Connellsville Day 1 and that was a little bit too long a day for me but the weather was great and I met up with some very cool people traveling in my direction. I did Connellsville to Pittsburgh relatively quickly on Day 2, arriving at Point State Park by midday. Lovely ride. Well maintained rail trail. Nice amenities all along the way. Beautiful scenery. Got lost a bit in McKeesport but found my way back relatively easily. Highly recommended. Now to go from Pittsburgh to DC!
Beautiful trail amongst the woods and along the stream.
This was my first ride on the C & O in years. I've stayed away due to rough gravel, pot holes, and rocks that even my hybrid couldn't overcome. But recently I heard that there had been resurfacing at Shepherdstown. What a world of difference! Crushed limestone that is compacted into a very level trail. We rode north from Dargan Bend to a couple miles past Shepherdstown. Dargan Bend was the closest parking lot we could find across from Harper's Ferry. Being there in late fall, the trees were bare but the river views were great. The trail north of Shepherdstown is gravel with rocks protruding here and there, making for a rough ride. We only traveled until hitting 10 miles from our start before turning back. Our timing couldn't have been worse as there was some kind of a foot race going on, but since we traveled 100 miles to get here we rode anyway. (I checked the NPS.gov website before going but saw no mention of the race, so not sure how one finds out about events on the towpath.) Overall, though, it was a great 20 mile ride.
Nice short trail. Good signs and not crowded.
Use caution when on a bike. Keep a low speed. While they seem to be making some improvements slowly, in spots the pavement is so broken up it’s nearly impassible. Additionally the side path dumps you off on to the mail road without a clear way how to connection and it doesn’t even exist for a couple of important blocks.
On 10/22/20 my friend and I rode the above stretch. It was absolutely beautiful! We were cautious due to the mornings heavy fog and all the damp leaves on the ground. Made the paths edges somewhat difficult to see. The trail was extremely smooth until you get to the Brunswick Waste Treatment Plant, where you share the dusty and bumpy road with big trucks coming and going from the plant. Pot holes were terrible there. But once back on the trail, it was a smooth sail. I believe it was around a 28-mile ride for us.
This is an easy trail for kids. They learn a little history and have fun. One of my kids danced on most of it. The loop is a good feature.
Very scenic route, paved bike path. We went on a Sunday after 2pm and it wasn’t crazy packed. It is true that there are a bunch of hills so be prepared for a workout. Definitely worth a try.
We did about twelve miles of the western part. Really pretty. We will be back!
This is a mid-level bike trail with plenty of off trail single tracking. Most of the path is paved. There are some rough areas which is why I say, mid-level. Your gonna carry your $3000 road bike. I would have been very happy on my gravel bike, but I chose my fixed gear road bike. I know! I didn’t read reviews, and I’m kicking myself for it! But I still had an awesome time carrying some of the way.
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