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 4247 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 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...
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...
Plan a full day (or two) for your visit to the Western Maryland Rail Trail (WMRT), a 22-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...
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...
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 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 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...
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 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 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 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 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...
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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...
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...
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 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 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...
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 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 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 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 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 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 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...
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...
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...
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...
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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 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...
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...
Plan a full day (or two) for your visit to the Western Maryland Rail Trail (WMRT), a 22-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 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....
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...
Plan a full day (or two) for your visit to the Western Maryland Rail Trail (WMRT), a 22-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....
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...
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...
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...
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 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 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...
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 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...
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 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 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 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...
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...
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...
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 new western extension to the Western Maryland Rail Trail is now open (May of 2019). It is an excellent ride with scenic views of the C&O Canal and the Potomac River. Also, you get to see how the Western Maryland RR was built into the side of the Potomac River valley with steep cliffs above the trail and down to the C&O Canal. You can see the western end of the Indigo Tunnel and the trail ends at the High Bridge over the Potomac River. The connections to the C&O Canal towpath are very nicely done. Thank you State of Maryland.
Fantastic trip through wester Pennsylvania
Flat and 100% paved makes for a nice, smooth bike ride. The WMRT parallels the C&O Canal from Big Pool, west through Hancock (about the half-way point), before ending at Sideling Hill Creek. Construction continues on the western end until the trail will eventually extend to Little Orleans.
There are a few areas where you can cross over onto the C&O canal.
Hancock offers a variety of services. I've ridden from Hancock, west on two separate rides, and will return.
WE DID THE ENTIRE C&O AND GAP RIDE WITH A GROUP OF 50 RIDERS IN 2007. IT WAS FULLY SUPPORTED AND JUST A WONDERFUL WEEK. WE STARTED IN WASHINGTON AND FINISHED IN BOSTON, PA.(THE TRAIL ALL THE WAY TO PITTSBURG WAS NOT YET OPEN). WE HAD PEOPLE FROM ALL OVER THE USA INCLUDING CALIFORNIA, OREGON AND ALASKA, AND A YOUNG MAN FROM IRELAND. THE PEOPLE NOT FROM EAST OF THE MISSISSIPPI KEPT SAYING THEY COULDN'T BELEIVE HOW BEAUTIFUL THE EASTEN U.S. IS. THEY ALWAYS THOUGHT OF THE EAST AS NEW YORK, PHILLY AND WASHINGTON, D.C.. AND THE ENTIRE RIDE IS EASY ENOUGH FOR A BEGINNER.
I RECOMEND THE G.A.P. AND THE C&O TRIP AT LEAST ONCE IN YOUR LIFE, AND TAKE A WEEK TO DO BOTH TRAILS WITH A GROUP.
Rode from Williamsport MD upriver to Ft Frederick in 2018. Same potholes and other trail safety issues (only worse) that we saw on our first ride in 2014. Shame there is no biking group in the area to take over and maintain what could be a fantastic ride.
I won't ride this part of the trail again.
Winchester isn’t friendly to bicyclists or runners. So I think in effort they tried to create a nice running/ biking loop but failed. The sidewalks are dangerous if you try to run on them in the city and the green circle still makes you have to run on such treacherous terrain. Also you still have to cross traffic. Pedestrian bridge would help but I know that’s costly. Bottom line it’s an effort made of a broken circle. Consulting runners would have been helpful.
This describes the first 7 miles of the trail from the south. I started at Occoquan Regional Park (more on this later), so traveled about 1.5 mi (all steeply uphill) before actually getting to the southern terminus of the CCT. I have to say that the trail is not well marked. Note that as you fly down Workhouse Rd the trail secretly takes a right without much signage. Also, as has been noted in previous reviews, the path through the prison area was very confusing, again due to lack of signage. After the prison, the trail continues with asphalt - thanks to the person who spray painted directional signals on the asphalt where users must make turns. I had fun crossing the creek several times. With the water level I dismounted only once. Otherwise plowed through the water like a kid! Not long after crossing Pohick Rd (approx 1.5 mi) the trail turned from asphalt to dirt/rocks. Encountered a newly fallen (I swear based on the fresh smell of the leaves and branches that it had fallen the night before) tree that required some nifty maneuvering. I continued on this for a bit, then decided to turn around. Will explore more of the trail later.
But, while parking at Occoquan Regional Park required a 1.5 mile uphill at the start, it provides a 1.5 mile downhill at the end. Plus, and this is the real bonus, you can coast right down to the Brickmaker’s Cafe and have a beer or two before you head out. I recommend the Port City Porter.
We rode it on a couple of sections..We parked at Deal ,road to Big Savage Tunnel & Eastern Continental Divide & little further & back..Then drove to Garrett & parked & rode to Salisbury Viaduct & Meyersdale Train Station,where we stopped . Some neat art work & gift shop. We ended up talking to a volunteer who was Brooke Folk,the local writer who writes about the trail & anyway about 2 weeks later he wrote about us ,which was cool!! He was a very interesting guy.We really enjoyed the trail. Next day parked in Harnedsville & rode to Pinkerton tunnel & little further then back..Had lunch then drove to Ohiopyle & rode about 15 more miles.We like to ride but are more casual riders,maybe 20-30 miles a day. Slight up hill in parts,but not bad.I would recommend getting the Trail Guide book. It is great & has a great map of all the high lights & towns. We will be back to ride other sections..such a great trail,nice towns & nice people..
I really liked this trail. While being a little frustrated on the Pittsburgh city trail, I discovered this one by accident and loved how nice it was. Near Pittsburgh it takes you through some nice Pittsburgh-esqe things.
Last week I rode from Leesburg to Falls Church on the WO&D -- it's a great trail with long flat segments and rolling hills, going through woods and fields all the way to Tysons and Vienna. Be aware that some of the intersections are dangerous, and toward the western, more rural end, many cars don't even bother stopping. But the trail is well-maintained with many opportunities for stopping (but very few of them with bathrooms, unfortunately).
My friend Tom Crotty and I rode the GAP Aug 2017-we had a great time but it was HOT!
This time we came a month later (sept 24-26) and brought along 5 riders new to the GAP!
We used same logistics again riding 1-way from Pitt to Cumberland:
* Day ONE 60 miles to Connelsville Pa -- stayed @ Seems Like Home B&B - Rick took excellent care of all of us and the breakfast he served was awesome!
* Day TWO - 45 miles to Rockwood PA - stayed @ Husqy Haven Cabin and at the Hostel-both were GREAT!
* Day THREE - 45 miles to Cumberland MD!
We hired the Cumberland Trail Connection to shuttle us with our bikes back to Pittsburgh. - Chuck was an excellent driver and took good care of us and our bikes!
The GAP must be one of the most beautiful rail-trails in the USA. Even though we got rained on for at least half of Day One and half of Day Two, none of us slipped, fell, or had any bike troubles... We still had a tremendously wonderful experience!
The sights are absolutely stunning - we heard and saw more running water than we would have if it had not been raining... the temp was very moderate
A GREAT time was had by all!
We already have a plan for the next time we return: We will stay in Cumberland and do a 4-day out and back ride to Connelsville!
Put this one on your Must-Ride list!
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