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 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 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...
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;...
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...
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 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...
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 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....
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 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...
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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...
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...
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 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...
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...
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 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 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 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...
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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...
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 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 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 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....
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 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...
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...
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 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...
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...
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...
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;...
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...
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 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 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 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 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 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 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...
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 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...
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 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 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...
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 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...
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..
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!
Towpath is nearly impassable from lack of basic maintenance over the past 20 years. Mud in places is over 8" deep. The tunnel has trees growing out of its face and the boardwalk has holes rotted through in many places. Such a shame that America can't maintain a simple bike path.
Enjoyable ride, some level areas and a few gentle rollers. Beginners may find it slightly challenging due to the hills but for the experienced rider it’s a cake walk. NOTE: there is no shade to speak of, take a camel pak and hydrate because it’s hot as hades and there is no escape from the sun.
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!
We rode Amtrak from Pittsburgh to Cumberland on June 30th. Fortunately the train was very late, so we didn't get on the trail until 3:30 and were able to avoid some of the sun we likely would have had earlier in the day. The climb to the Continental Divide was long and slow, but beautiful. We stopped to take quite a few pictures and chilled for a bit in Frostburg (ice cream shop closed at 4 on a 90 degree Saturday?!?). Stayed at Morguen Toole Co. in Meyersdale and enjoyed a great meal there too. On July 1 we headed to Confluence in the AM. We borrowed a car to visit the Flight 93 Memorial and, once again, managed to avoid riding in the hottest part of the day. Once on our way again we headed to Connellsville and stayed at the Connellsville B&B, which was wonderful. On the 2nd we rode to West Newton for lunch, after an extended stop at Rachel Sager Mosaics in Whitsett. We had a stop at Over the Bars Bike Cafe in Pittsburgh before finishing up the trail just before a thunderstorm hit. We met some wonderful folks along the way and enjoyed a fantastic few days of riding at an enjoyable pace.
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.
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