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 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...
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...
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 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...
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...
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...
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 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 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 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 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....
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 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...
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 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 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...
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...
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 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;...
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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 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 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 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...
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...
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 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 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 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 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 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...
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 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 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...
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 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...
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 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...
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...
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 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 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 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 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 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...
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...
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 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...
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.
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.
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.
I rode the GAP /CO this past Labor Day weekend- best bike trip ever. 120 miles from Pittsburgh to Meyersdale (120 miles). Almost flat- never any sense of climbing, smooth trail on a road bike with 32mm tires and fenders. The ride from Meyersdale to Cumberland was easy- downhill the last 30 miles or so. Thanks to all the groups that put the trail together- what an asset to the region.
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.
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