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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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 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 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....
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 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...
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 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 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 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 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...
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...
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...
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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...
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 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 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...
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 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 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 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 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 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...
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 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 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 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 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....
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 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...
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...
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;...
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...
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 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 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...
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...
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;...
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 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...
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...
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 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 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 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 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...
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 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...
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 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 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....
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 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!
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.
If you're okay with riding along side traffic, and stopping at red lights, then this "trail" might be for you. The local commuters don't appear to be very bike friendly. After hubby almost got hit by a car when we had the blinking right of way, and the next car almost clipped me, we turned around and left the "trail". Perhaps it is better done by foot. A lot of hills, not flat. Paved and concrete sidewalk. The park is nice, but cyclists are not permitted to ride around it. We chose to explore Shenandoah University by bike, and may returns to this path as walkers instead of cycling. Maybe you'd like this circle, but it is not for us. Happy Trails!
It is a wide sidewalk with plenty of room to pass people. It is smooth and very stroller friendly. The traffic along side it can be very busy and loud. There are a few larger hills.
This was our first long bike adventure ever. I've been retired several years and my wife retired last summer '16 from teaching. She had been a complete academic and never was interested in sports except when our kids were involved. Now, she loves exercising and gym workouts. We've done single day bike excursions, but nothing like this. We started in Homewood (Pittsburgh area) and rode far (52 miles) for rookies on the first day, to Connellsville. Unbelievably beautiful natural environment surrounded us every stroke of the pedal. First night we stayed at the Connellsville B&B and were very impressed with immaculate cleanliness, delicious breakfast, and pleasant owner, Lucille. After our 52-mile day, I was worried about my wife's physical well being, but by the next morning she felt much better and we were glad we had planned a much shorter ride (28 miles) Day 2 to Confluence. There, we stayed overnight at Parker House, also a pleasant stay, though no breakfast is included. We purchased simple breakfast food items at the local grocery store. The third day was our longest ride (62 miles), planned knowing the last 24 miles into Cumberland are downhill. Our daughter, husband, and granddaughters were waiting at Mile Zero with flowers and cheers. Just a beautiful, enjoyable, and educational trip. And you meet the kind, helpful, friendly people on the trail that help make this world a better place. Outstanding scenery, cool shade on hot days thanks to beautiful vegetation, historical passageway with awesome bridges and tunnels, well-maintained trails. We can't wait to do it again!
Can't say more been riding the YRT trail for years!!
Also, you can see cool rocks and things from the bridge. The spiral staircase to get up to the bridge was not built with bicyclists in mind.
I did this trail as a little side trip off the C&O. I think its name is actually Knobley Tunnel Trail. Unmarked from the Maryland side, but it's right beside the remnants of a railroad trestle. My first tunnel on a bicycle - quite the experience! Incredibly humid!
This is a 22 mile smooth asphalt trail that is great for Road bikes, and gives a 44 mile roundtrip run. I managed over 500 miles on this trail during the month of June 2017 starting at Big Pond and riding the length of the trail each time. I averaged over 17 miles an hour so it is a great trail for just riding, it is pretty quiet especially during the week and is well shaded for summer use. Highly recommend and worth the drive to go an enjoy.
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