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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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...
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 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...
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...
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...
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 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 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 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...
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...
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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...
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 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 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 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....
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 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...
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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...
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 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....
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 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...
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...
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;...
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 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 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 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...
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 old Warrenton Branch Spur railroad, running 1.5 miles between the trailhead behind the restaurant at the depot in downtown Warrenton (4th St....
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...
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 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 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 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 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 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...
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 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 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....
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 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 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 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...
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...
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...
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 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...
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 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 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 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...
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...
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 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....
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...
I wish I read the reviews before taking my road bike on this trail. I started at the Lorton entrance and the trail quickly became mud and gravel. My road slick tires were definitely ill equipped for this segment of the trail. Better for cyclocross and mountain bikes.
We love this trail and wouldn't mind riding it again someday. We had to travel to get to it so we stayed at a hotel in Hancock, MD so that we could ride the western half one day and the eastern half the next. I can't say I would recommend the America's Best Value Inn. We travel with a camper now, thank goodness. But the trail was just lovely and I recommend it.
Rented bikes from Cumberland Connection (they were AWESOME!). We didn't get on the trail till 4:30 and made it to Gunter Hotel in Frostburg by sunset at 6:29. It is a lot of uphill walking from the trail to downtown Frostburg. Ask for room with new beds at Gunter and make sure and go to the mens bathroom to see the 'jail cell'. Ate at Shift which was amazing! We were on the trail by 8:40am, lunch at Rockwood (Rockwood Mills-the dessert were amazing!) by 12:30 and made it to Confluence by 3:30 for our shuttle pick up . We stopped many, many times for pictures! I hardly wanted to blink because this was such an amazing, beautiful experience!
We got a wonderful work-out on this trail, but the hills were not overly difficult. we biked late afternoon/evening in October. We started on the Martinsburg end, which is definitely hillier that the east end. We stopped for coffee at the Black Dog on the way back. It was a perfect stopping place, with nice bathrooms.
Great trail for multi-day ride with motels or camping, or single day rides. I had to find parking locations in order to ride several days, with Round trip rides of 40-60 miles/day (20-30 each way). A few confusing spots and a couple steep spots. Quite confusing in Pittsburgh, where markings are absent, and trail goes through the city streets, but lovely to arrive at Point State Park fountain. Cedar Creek Park especially lovely area, with camping (but gates lock at sundown so don't park late). Great long ride down gentle hill from Deal, MD (highest point on trail) to Cumberland. Long uphill ride back up 26 miles from Cumberland back to Deal. Beautiful trail.
From hundreds of cars to the overhead planes landing at a nearby airport, this trail was full of urban noise. The challenging hills, the asphalt trail and the geocaches were a plus but, for me, prefer a trail more serene.
This wonderful trail is just far enough from the heavily populated Baltimore/Washington area that it is never crowded. Even on "busy" weekends you'll pass just a few other friendly folks who enjoy biking enough to make the trek to Hancock. For us "weird" recumbent trike riders there are a few teeth rattling tree roots pushing up the asphalt in places. Regular bikes with even modest suspension or fat tires will barely notice them. Enjoy this wonderful gem of a trail!
I have ridden this path several times. There are many hills and some come straight down to a stop to cross the road. After which, you then pedal straight up hill. However, the path is quite do-able. There are two treats for you on this ride - 1) a stop at Black Dog Coffee and at the Martinsburg end, you can cross the highway (carefully) to find the Berkeley County Human Society and visit with the pooches! Enjoy and cycle safe!
This is an excellent trail. Smooth pavement. Places to stop along the way for snacks or restaurants. Good scene scenery along the c&o canal. and can see the river in places. But the eastern end is next to highway 70 is is pretty noisy.
Tom Crotty and I rode the GAP 25-27 Aug 2017 from Pittsburgh (mile 150) to Cumberland (mile 0). I drove in and Tom flew in from Raleigh, NC. Approx. miles: Day1-60, Day2-45, Day3-45. We used a B&B in Connelsville and a B&B in Rockwood. The climb up to the Eastern Continental Divide during Day1, Day2, and half of Day3 was so gradual, it never worked us hard! Mile 150-128 were paved. The fine-crushed gravel trail was in excellent shape! The wild flowers were blooming and the rivers, that the GAP follows for about 80%, were flowing nicely. We stopped @ every major bridge crossing to soak in the beauty of the GAP! Because we rode in summer on Friday-Sunday, we had no trouble finding good food and ice for our water bottles. Warning - The celebratory beers for each end-of-day can only be purchased @ an eating establishment? About 730pm on Day3, we enjoyed a relaxing ride on AmTrak back to Pittsburg (it only made 1 stop @ Connelsville) - I easily biked back to 1st Ave Parking Lot where I had parked my truck. My bro, Al, and I rode 190miles of the KATY trail 3 days Aug 2016, and we had a great time; but the GAP impressed me as much or more. In my opinion, the GAP has more admirable beauty - more often! Although my goal is to ride 1-2 new rails-trails each year, Tom and I have discussed the possibility of returning in the Fall, just to ride the 2-days from Connelsville to Cumberland; I think those 2 days were the most impressive! Every Biker should set the GAP on their dream-trail list!
Great smooth trail that is well kept and full of wonderful scenery. Highly recommended.
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