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...
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...
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 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 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...
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 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 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...
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...
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...
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...
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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 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 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...
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 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...
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 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 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....
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...
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 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 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 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 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 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 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...
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 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...
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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...
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...
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 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 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 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 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 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...
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...
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 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 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 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...
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 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 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...
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 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 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...
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...
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;...
I had never spent much time on the Mon in years past but was more than pleasantly surprised by the quality trail starting near downtown. We went all the way to McKeesport and next time I plan on going further to link up with the Montoya trail. Well maintained and ample facilities along the way with a number of great river and city views!
Scenic trail, plenty of wildlife, perfect for walking or biking!
One of Maryland's top rail trails for scenery and the amenities in Hancock. However the asphalt surface is becoming a problem due to tree roots. The bumps are frequent and painful, especially on a road bike. Several riders on hybrids also complained. Trail managers need to get on top of this before bikers begin to abandon the trail. Even if repaving is not possible, a milling machine can help smooth out the bumps.
I’ve ridden the entire C&O Canal Trail three times and shorter sections several other times. It is a great trail for its natural beauty as well as historic significance, with one big caveat. You need to pay close attention to the weather and trail conditions because it can become an awful mess after heavy or extended rains and flooding. The first two times we rode the entire C&O (as well as the GAP), we had dry weather and the trail was very rideable except for occasional mud puddles. However, the third time in June 2018 followed several weeks of heavy rains and flooding, and the trail was impassable in many spots. We had to hire shuttles to carry us around two sections, and we were bogged down by thick mud and downed trees in some of the sections we rode. I will follow trail and weather reports more closely if I ride the C&O again.
I started at lock 6 and rode up to Great Falls Tavern. It was a great day. I saw a deer, a few herons, and the water was high on the Potomac. Trail was under construction in two places along the trail during my ride including at Great Falls. Still it is an enjoyable ride with lots of share on hot days.
Good area to walk, jog, run, bike, ..... our dog loved it as well.
One of our favorites. About 3 miles on west end closed because of mud slides. Rest of trail good, but tree roots are starting to make some sections bumpy.
This is one of the best trails in the east coast. Long, well maintained, and very varied along the way. You can connect with the Capital Crescent Trail through the Custis Trail and complete a century going back and forth.
Yes, some portions of the trail are under electric towers but is still a great trail to ride.
There is a Barbeque restaurant (Carolinas Brothers) in Ashburn, where you can have the best pulled pork sandwich with cole slaw and beans!
The end of the trail at Purcelville is anti-climatic. You end up in a town that seems to be oblivious to the bike trail.
Fortunately, the old train station has bathrooms with hot water! Unbelievable!!!
The Warrenton Branch Greenway is a beautiful little connector trail. On a Tuesday morning, we saw folks out biking, jogging, and walking their dogs. During our early May visit, the trail was shady and green with lots of flowering bushes alongside. At the downtown Warrenton trailhead, we were also greeted by a little red caboose, which was cool to see. There were a couple of street crossings on quiet residential roads, but they were well marked and the drivers were courteous and happy to stop and let us cross.
Rode part of this trail from Purcellville to Leesburg. We were short on time so only got to ride 7 miles out and 7 miles back. Loved the trail. Quiet, nicely paved, marked well and rural when you start out at the Purcellville end. Hope to go back and ride another section again and eventually cover all of it after a few rides!
I rode from the trail head in Big Pool, MD to the fruit market about 8 miles away on Thursday, 4/26/18. It was a sunny day, 65°. I rode through a sparsely populated area and then paralleled the C&O canal for the rest of the way. The foliage is not in bloom yet so it is not so much a joyous experience as a healthy ride in cool weather. There was a road biker taking advantage of the paved asphalt surface riding at a fast clip. There were also a few other riders on comfort bikes enjoying the scenery like myself. I would recommend this trail to anyone who is tired of crushed gravel surface rail trails but still want that rail-trail feel. This trail parallels I-70 so it is a bit noisy. For this reason I give it only three stars.
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