Winchester, VA Hiking Trails and Maps

545 Reviews

Looking for the best Hiking trails around Winchester?

Find the top rated hiking trails in Winchester, whether you're looking for an easy short hiking trail or a long hiking trail, you'll find what you're looking for. Click on a hiking trail below to find trail descriptions, trail maps, photos, and reviews.

  • Relevance
  • Name
  • Length
  • Most Popular
Activities
Length
Surfaces
Type
36 Results
Activities
Length
Surfaces
Type

Ballenger Creek Linear Trail

4.2 mi
State: MD
Asphalt, Concrete

Black Hill Trail

4.5 mi
State: MD
Asphalt, Dirt

Chesapeake & Ohio Canal National Historical Park

184.2 mi
State: DC, MD
Brick, Concrete, Crushed Stone, Dirt

Ed Miller Memorial Trail

2 mi
State: PA
Asphalt

Great Allegheny Passage

153.22 mi
State: MD, PA
Asphalt, Concrete, Crushed Stone, Dirt, Gravel

Great American Rail-Trail

3743.9 mi
State: DC, IA, ID, IL, IN, MD, MT, NE, OH, PA, WA, WV, WY
Asphalt, Concrete, Crushed Stone

H & F Trolley Trail

1.1 mi
State: MD
Asphalt

Powerline Trail (MD)

6 mi
State: MD
Dirt, Grass

Rocky Run Stream Valley Trail

4.6 mi
State: VA
Asphalt, Crushed Stone

Unfinished Railroad Loop Trail

1.2 mi
State: VA
Dirt

Warrenton Branch Greenway

2 mi
State: VA
Asphalt

Washington and Old Dominion Railroad Regional Park (W&OD)

44.4 mi
State: VA
Asphalt, Crushed Stone

Western Maryland Rail Trail

27.5 mi
State: MD
Asphalt

Carpendale Trail

0.8 mi
State: MD, WV
Crushed Stone

Gerry Connolly Cross County Trail

40 mi
State: VA
Asphalt, Ballast, Concrete, Crushed Stone, Dirt, Gravel

Harpers Ferry Railroad Bridge

0.14 mi
State: MD, WV
Boardwalk

Hawksbill Greenway

2 mi
State: VA
Asphalt

Linton Hall Road Trail

5.4 mi
State: VA
Asphalt

Meadowlark Connector Trail

1.25 mi
State: VA
Asphalt

WV Route 9 Bike Path

10 mi
State: WV
Asphalt
Accordion

Centreville Road Sidepath

4.7 mi
State: VA
Asphalt

Cub Run Stream Valley Trail

9.1 mi
State: VA
Asphalt

Fairfax County Parkway Trail

28.3 mi
State: VA
Asphalt

Stringfellow Road Sidepath

3 mi
State: VA
Asphalt, Concrete

Sudley Manor Drive Trail

4.3 mi
State: VA
Asphalt

Winchester Green Circle

5.3 mi
State: VA
Asphalt

Braddock Road Sidepath

10 mi
State: VA
Asphalt, Concrete

Carroll Creek Path

3 mi
State: MD
Asphalt, Concrete

East Street Rail Trail

0.8 mi
State: MD
Asphalt

Folly Lick Branch Trail

2 mi
State: VA
Asphalt

Herndon Parkway Sidepath

2 mi
State: VA
Concrete

Second Manassas Trail

6.7 mi
State: VA
Dirt, Grass

West Ox Road Sidepath

2.9 mi
State: VA
Asphalt

White's Mill Trail

1.3 mi
State: VA
Asphalt
Trail Image Trail Name States Length Surface Rating
The Ballenger creek Linear Trail is a 4.2 mile greenway in Frederick County Maryland. Constructed by both local developers and the county government, whose goal was to connect the community, the trail...
MD 4.2 mi Asphalt, Concrete
Overview Black Hill Trail offers a 4.5-mile wooded trek with gentle inclines through Black Hill Regional Park in Boyds, Maryland, just outside of Washington, D.C. The trail is primarily paved,...
MD 4.5 mi Asphalt, Dirt
Overview Following the Potomac River, the C&O Canal Towpath traverses the Chesapeake & Ohio Canal National Historical Park for 184.2 miles between Cumberland, Maryland, and the Georgetown...
DC, MD 184.2 mi Brick, Concrete, Crushed Stone, Dirt
Named in honor of the late Ed Miller—a longtime caretaker at Renfrew Park and Museum and member of the Waynesboro Historical Society and Renfrew Institute—the Ed Miller Memorial Trail connects three...
PA 2 mi Asphalt
Notice: There are a couple detours along the long GAP route. For all trail notices, see GAP website for more current information. Overview Ever since the Great Allegheny Passage (GAP) was...
MD, PA 153.22 mi Asphalt, Concrete, Crushed Stone, Dirt, Gravel
Note: This developing route is not yet fully contiguous – it is just over 50% complete. Please refer to the Trail Map for more information on the existing sections of trail, as well as the online...
DC, IA, ID, IL, IN, MD, MT, NE, OH, PA, WA, WV, WY 3743.9 mi Asphalt, Concrete, Crushed Stone
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...
MD 1.1 mi Asphalt
This trail traces a hilly green swath located in a Pepco electric utility right-of-way that stretches between South Gernmantown Recreational Park and Muddy Branch Stream Valley Park. It's a natural...
MD 6 mi Dirt, Grass
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...
VA 4.6 mi Asphalt, Crushed Stone
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...
VA 1.2 mi Dirt
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...
VA 2 mi Asphalt
Overview  The 44.4-mile Washington and Old Dominion Trail (W&OD), one of suburban Washington, D.C.’s most popular rail-­trails, is a fantastic link between the state’s rural and historical past and...
VA 44.4 mi Asphalt, Crushed Stone
Overview Hugging the picturesque Potomac River and the C&O Canal Towpath, the Western Maryland Rail Trail (WMRT) rolls for nearly 28 miles through Maryland’s narrow panhandle wedged between...
MD 27.5 mi Asphalt
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...
MD, WV 0.8 mi Crushed Stone
Overview The Gerry Connolly Cross County Trail is a multi-use trail that follows along the various stream valleys in Fairfax County, Virginia for 41.4 miles. It is officially named the Gerry...
VA 40 mi Asphalt, Ballast, Concrete, Crushed Stone, Dirt, Gravel
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...
MD, WV 0.14 mi Boardwalk
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....
VA 2 mi Asphalt
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...
VA 5.4 mi Asphalt
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;...
VA 1.25 mi Asphalt
Overview The WV Route 9 Bike Path follows the busy thoroughfare from Martinsburg to the Charles Town/Ranson area. About the Route Note that the path runs through open space with little to no...
WV 10 mi Asphalt
Accordion
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...
VA 4.7 mi Asphalt
The Cub Run Stream Valley Trail offers a paved route meandering through Cub Run Stream Valley Park in the Northern Virginia suburb of Centreville. Though it's surrounded by residential neighborhoods,...
VA 9.1 mi Asphalt
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...
VA 28.3 mi Asphalt
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...
VA 3 mi Asphalt, Concrete
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...
VA 4.3 mi Asphalt
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...
VA 5.3 mi Asphalt
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...
VA 10 mi Asphalt, Concrete
Overview The Carroll Creek Path runs for 3 miles through the heart of Frederick, MD. About the Route The Carroll Creek Path leaves off in the north from Rosemount Ave., near the Schifferstadt...
MD 3 mi Asphalt, Concrete
Running along N. East Street in Frederick, this very short segment of trail is built on a former rail corridor. There are plans to extend the trail along the former Walkerville Southern Railroad...
MD 0.8 mi Asphalt
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...
VA 2 mi Asphalt
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...
VA 2 mi Concrete
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...
VA 0.3 mi Crushed Stone
Leading visitors through the final events of the Second Battle of Manassas in the Manassas National Battlefield Park, this trail is comprised of several connected loops with a number of short spur and...
VA 6.7 mi Dirt, Grass
Right in the middle of the Herndon suburbs, the Sugarland Run Stream Valley Trail provides an Oasis for hikers and bikers looking to escape into the woods. For it's nearly 3 mile run, the trail...
VA 6 mi Asphalt
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...
VA 2.9 mi Asphalt
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...
VA 1.3 mi Asphalt

Recent Trail Reviews

Chesapeake & Ohio Canal National Historical Park

Simply spectacular

June, 2025 by ethantabor

I just finished a two-day solo tour (Cumberland to Williamsport, Williamsport to DC) and had an incredible experience despite the rain and the tough going over a few stretches. I hear a lot of criticism about the C & O, particularly when compared to the GAP (which I have also done). I appreciate the contrast and hope that the C&O retains its historic character as a more rugged towpath (not a rail trail). That said, the conditions on the east side of Paw Paw and from White’s Ferry to DC were challenging (again, I like the changing surfaces). Highlights: wilderness character, Paw Paw Tunnel, sycamores between Harper’s Ferry and Antietam, Great Falls, Monocacy, Point of Rocks station and the towns.

Chesapeake & Ohio Canal National Historical Park

A Disappointment

June, 2025 by redebski

My son and I rode the C&O the first week of June '25 as part of a ride from Pittsburgh to Washington DC.

I am going to preface this review making it clear that it was an unusually wet Spring and significant damage has occurred due to flooding. Kudos to the efforts to repair the damage and keep the trail open. There were numerous detours off of the trail but it was open and passable. However, had I not taken this into consideration, and had not just completed the GAP as a comparison, I would have rated the trail 2 stars.

Here are my key issues rated from most, to least, significant:

1) The terminus of the trail in Georgetown is inaccessible due to construction. We rode 334 miles in 5 days to unceremoniously end our accomplishment carrying our bikes up a series of stairs, only to encounter detour signs that literally pointed in all four directions. After a half hour walking through urine-laden alleys searching for mile 0, a bicycle cop told us that we were as close as we could get. Our victory picture was taken next to a detour sign, each of us providing a middle-finger salute.

2) The trail surface through the Paw Paw tunnel can only be described as interconnecting pot holes filled with 6" of water. Had there not been other traffic in the tunnel, it may have been rideable. Just accept that you will get the opportunity to stretch your legs for a half-mile walk in the dark. Your shoes will eventually drain and dry by the time you arrive in DC.

3) For 15-20 miles south of the Paw Paw tunnel the trail is unmaintained. The riding surface is basically sunken truck tire tracks, separated by a hump of uncut weeds. The tracks themselves were devoid of any gravel which ensured that you were riding in either water or mud. The weeds on both sides of the trail had yet to be trimmed and had encroached into the tracks. The good news is that we were concentrating so hard on keeping our bikes upright in the slop, we didn't have time to think about the ticks. Anyone who has hiked the Adirondack high peaks knows exactly what I am describing.

4) Most of the trail repairs have been made with loose, coarse, crushed stone. I was fortunate to be riding a mountain bike with 2" tires at 60psi. My son was riding a gravel bike with 40mm tires which mean he was riding sideways much of the time. He ended up riding a combined total of 400 miles considering the lateral component of his travel.

5) Where washouts had yet to be filled with the previously mentioned stone, you have to cross crevices 6-8 inches deep. Not such a big problem if you were travelling slow enough to identify them before jamming your arms through your shoulders and ramming your saddle through the softer tissues of your rear end.

6) Having camped in Assateague for half my life, I thought that I knew aggressive mosquitoes. However, since the trail is totally devoid of any breeze, the stabbing critters locate you as soon as your bike comes to a halt. The good news is that we saved time taking breaks.

I will be posting a 5-star review for the GAP next. If you average the two scores together, the total trail experience was a 4. That still makes the ride from the 'Burgh to DC worthwhile. Just be prepared for the unexpected challenges.

Great Allegheny Passage

well maintained, pretty area

April, 2025 by astroman

PA-Cumberland 5/2023. Loved this trail with lots of places to camp, a winding and entertaining trail, views of the river, tunnels, small towns along the way. I particularly liked Frostburg and camped two nights. The switchbacks up to town aren't as miserable as some describe and the view is rewarding. The Toasted Goat in Hotel Gunter is an old hotel worth a walk around and a meal. Check out the basement holding cell and speakeasy.

Accordion

Western Maryland Rail Trail

completely resurfaced 5 star

April, 2025 by aldo_desalvo

I rode this for a second time recently. The trail is in great shape. I will they would add the path through the tunnel. Extending the trail over the three bridges would make this the best in the area. Not sure if that is a plan. Hancock is a great town. Very remote in little orleans

Western Maryland Rail Trail

Wmrt 2025 all repaved

April, 2025 by loisslong

This is my favorite paved trail. All the bumps and roots are gone since the repaving project was completed in fall 2024. Hancock is the town at about the middle mileage. The western end is quiet through the woods. There are very few road crossings and it's pretty flat grade. Berkeley Springs WV is only 6 miles south of Hancock MD and that's a cute tourist town to visit. There's also a good bike store in Hancock.

Great American Rail-Trail

Warden to Lind

April, 2025 by howmarplus3

Ok section, kind of dull. Agriculture & cows. Found a bit of shade by a grain elevator for lunch. Several washouts filled with tumbleweeds as you get closer to Lind.

Harpers Ferry Railroad Bridge

Difficult but doable for cyclists

February, 2025 by luv2bike23

The railroad bridge appears to be the only way to access the C&O Canal Towpath directly from Harpers Ferry. It's narrow and congested in the warmer months, and walking a bike across the bridge can be challenging. More difficult is the tight spiral staircase descending to the towpath from the bridge. It's not exceptionally strenuous with a light bicycle but I wouldn't attempt it with a heavy E-bike. Once at the bottom, the towpath is a beautiful cycling experience and it's also an easy walk to the Maryland Heights trail with its Civil War fortifications and fantastic overlook of Harpers Ferry.

Rocky Run Stream Valley Trail

easy wooded trail

November, 2024 by eklic

I just completed walking the main trail in both directions. Two days of hiking, with about 10,000 steps each day. I started by parking in a shopping mall lot about 1/3 of a mile from the eastern end trail head. In retrospect, the trail is near residential homes. I could have parked on the street and accessed the trail with a public access point. It is a lovely trail. The one downside is that i was never really in the woods. From almost every point on the trail, one can see the back of somebody’s house. This is more pronounced on the eastern half. The prettiest is within Ellanor C Lawrence Park.

Chesapeake & Ohio Canal National Historical Park

Rough with Rider-Beware Hazards

October, 2024 by morgan.paul511

I biked from Pittsburgh to DC (GAP and C&O trails combined) 9/8 thru 9/14/24. This review is for the C&O only. Weather – excellent. Scenery- beautiful. Accommodations – very good. Trail surfaces –highly variable from narrow dirt paths laced with muddy holes to relatively smooth, hardpacked dirt to loose gravel (better for a pickup truck than a bicycle!). From 10 miles south of Great Falls into DC the trail/road was especially rough. I was riding an Off-road bike with 40 MM wide tires and momentarily lost front tire stability in MANY spots due to loose gravel (especially on the sloped paths leading into & out of lock areas). My biggest safety concern were the numerous concrete bridges over creeks & culverts that had ZERO guard rails, warning signs or even yellow paint. The bridge widths were narrower than the trail requiring the biker to NOTICE and move more to the center for safety. If a biker went off the side of any of these bridges, I’d expect serious injuries or worse. The worst safety hazard was at Lock 38. Approaching the lock from the southwest side, the (main) trail leads right across the top of the lock wall- that is 3 to 4 ft wide with only an outer rail – very dangerous. The drop off to the grassy floor below was about 7-9 feet straight down. I was in a group of riders that suddenly saw this “tightrope” situation and jammed on their brakes. (Nobody realized we should have diverted onto a narrow, unmarked path that led downward through the lock.) Fortunately, everyone stopped safely; walked their bikes down a slope and on to the safe path through the bottom of the lock. A simple, cheap sign could prevent the near-miss accidents at this spot.
I’m really disappointed that this National Park hasn’t (at least) marked these safety hazards. Considering all the hazards and the rough gravel, I think this C&O Towpath trail merits 2 stars.

Great American Rail-Trail

such a beautiful trail!

October, 2024 by sherryschie

We started in Akron and rode about 18 miles north. Loved it!!!

Great Allegheny Passage

Epic ride, bucket list achievement.

October, 2024 by biknbob51

My wife had a yen to do a through ride and chose the GAP trail as her goal.
We spent 5 days on the trail, starting in Pittsburgh, and finishing in Cumberland. Even with drizzling rain on several portions of the ride, we both count this as one of the best we ever rode.
The trail surface is so consistently even, it is easy rolling, especially once you cross the Eastern Continental Divide, where it steepens a bit, downhill. There was literally no trash to be found along the trail, and any debris from trees, like limbs, was quickly removed by the crews that do that. There were times when we rode many miles without seeing another rider, or crossing a road. Along the way we noticed many places to take a break, with benches or shelters, and near each trailhead you will find a bike maintenance stand, with tools and air pump. We stayed in Pittsburgh, Boston, Connersville, Confluence, Meyersdale, and finished in Cumberland. All the lodgings were very nice, and we left our vehicle at our hotel in Pittsburgh ( paid to park it there ) and hired a livery service to get us back from Cumberland to the steel city. If you are considering this trail, go do it ! It was great.

Gerry Connolly Cross County Trail

The entire Gerry Connolly trail

October, 2024 by eklic

I recently walked virtually every foot of the 40+ mile long Jerry Connolly Cross County trail, in both directions. This includes the part of the route which is not a trail at all, but a 2-mile long sidewalk along a busy road. I would start by driving to a starting point and walk about 5000 steps in one direction, stopping at a convenient point where I could park my truck nearby. Then, I walked back along the same trail. Most of the southern part of the trail, from the Occoquan river to Arlington Blvd is paved in asphalt. Almost all of the northern part, from the Oakmont rec center to Great Falls park is a rough trail. This part would be quite muddy after a rain. Most of the trail parallels a stream, from Difficult Run in the north, to Accotink Creek in the middle, to Pohick Creek in the south. Trail markers range from excellent in some parts to hardly noticeable in other parts. Having Google Maps on a phone app was super helpful at times when I accidently veered from the trail, or was at a point with a fork in the trail. There are several signs along the way with a map of the trail in the near vicinity. These were necessary and helpful when the trail came to an apparent end and the resumption point was several yards away. Almost all of the trail is an easy walk with just a few steep-ish ascents and descents. Most of the trail is really quite pretty. Overall, a very fulfilling experience for me.

Find Nearby City trails

Register for free!

Register for free with TrailLink today!

We're a non-profit all about helping you enjoy the outdoors
  • View over 40,000 miles of trail maps
  • Share your trail photos
  • Save your own favorite trails
  • Learn about new trails near you
  • Leave reviews for trails
  • Add new and edit existing trails

Get the Free TrailLink App

The trail is always better with TrailLink

Scan the QR code to get TrailLink on your phone

Explore by City

Explore by City

Explore by Activity

Explore by Activity

Log in to your account to:

  • View trail paths on the map
  • Save trails to your account
  • Add trails, edit descriptions
  • Share photos
  • Add reviews

Log in with Google

Log in with Apple

OR

Register for free!

Join TrailLink (a non-profit) to view more than 40,000 miles of trail maps and more!

Register with Google

Register with Apple

OR

Your account has been deleted.