Winchester, VA Inline Skating Trails and Maps

553 Reviews

Looking for the best Inline Skating trails around Winchester?

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

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Activities
Length
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19 Results
Activities
Length
Surfaces
Type

Ballenger Creek Linear Trail

4.2 mi
State: MD
Asphalt, Concrete

Ed Miller Memorial Trail

2 mi
State: PA
Asphalt

H & F Trolley Trail

1.1 mi
State: MD
Asphalt

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

Gerry Connolly Cross County Trail

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

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

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

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

Folly Lick Branch Trail

2 mi
State: VA
Asphalt

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
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
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
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
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 the nation’s...
VA 44.4 mi Asphalt, Crushed Stone
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 Pennsylvania and...
MD 27.5 mi Asphalt
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 Connolly Cross...
VA 40 mi Asphalt, Ballast, Concrete, Crushed Stone, Dirt, Gravel
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
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 shade. While...
WV 10 mi Asphalt
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. About the Route While the paved trail varies in width and...
VA 28.3 mi Asphalt
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
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
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

Great Allegheny Passage

well maintained trail, beautiful scenery

October, 2025 by cjb1937est

Just got done this trail 10/9. Gap trail is a wonderful easy ride. Places we stayed were awesome! Bright Morning B&B, Ohiopyle suites. We stayed in the Karly. It was great! Right off the trail!! Coffee shop is great too. They also have a laundromat. We then traveled to Meyersdale where we stayed in the hotel airstream! Gotta stay here! It was great! Know that if you need to take the train back to Pittsburgh like we had too, it can run late. 5hrs for us. We met so many nice people along the way. That’s what I think of when I think of this trail!

Carpendale Trail

Trail is not well-maintained.

October, 2025 by stanlmaz

I decided to park in Cumberland on my way home from a trip to WV and ride down the C&O towpath to ride this trail.

I was disappointed in the state of the trail. It appears as if no one is maintaining this trail.

The path on the Maryland side is now almost covered with encroaching weeds.

The bridge is in good enough shape to permit you to ride across to West Virginia for the time being but it looks a little iffy. If no one is taking care of this trail the wooden planks may need replacing. At some point it may become a dangerous crossing when these planks start rotting.

The tunnel is blocked off so you can go no further than the WV side of the bridge.

I would recommend that riders skip this trail until such time as it is maintained.

Great Allegheny Passage

great trail for a beginner trail rider

September, 2025 by lob4fun

We just finished the GAP trail & C&O towpath 9/20 from Pittsburgh to DC. We took 8 days and our days ranged between 32 miles to 63 miles. Highly recommend this trail. Well maintained, accessible and clean port a John’s, always had plenty of toilet paper and were frequent enough to remove any anxiety about not being able to relieve yourself in privacy. Potable water was available along the trail which we still used a filter just to be safe. Beautiful trail, friendly riders and towns to visit. We rented a full sized SUV in DC and dropped it off at the Budget on Stanwix St just two blocks from fountain starting point. Worked perfectly to get going on our ride without delay.

Accordion

Chesapeake & Ohio Canal National Historical Park

Rough ride for a first timer trail rider

September, 2025 by lob4fun

This is probably the most I could handle on a bike ride. We rode the GAP and C&O back to back like many do in 8 days. It was great fun but the C&O is noticeably rougher, fewer port-a-Johns and very scarce potable water sources. On our 7th day from Williamsport to Brunswick we ran out of water midway and rode the remaining 25 miles without water. Fortunately the shade offered by the beautiful canopy of trees made it bearable. We made sure to load up on extra water on our final day. The mix of loose sand that caught us by surprise & the larger stones on the trail made for a more challenging ride than expected. On the one rainy day we had from Cumberland to Little Orleans, some of the puddles we encountered offered a new sense of “oh dear” as we didn’t know how deep the hole we were riding thru when there was no room to go around the puddle.

Great Allegheny Passage

Great ride on a great trail.

September, 2025 by joanna10_tl

I just completed the entire GAP. It was well worth it. The trail was in good shape and there was not too much traffic. I’d like to do it again.

Western Maryland Rail Trail

Open the Tunnel

September, 2025 by jandre

Biked from Hancock to Little Orleans and return on August 30, 2025. Distance: 34.5 miles. Stopped for lunch at Bill's Place in Little Orleans and got good food and friendly service. The paved portion of the trail is in excellent condition -- thanks to the Maryland Park Service for recently repaving the trail. The only negative is the 3-mile detour on the C & O Canal towpath around the abandoned Indigo tunnel. The towpath detour is unpaved and has a rougher surface than the trail. The nearly one-mile long tunnel was closed in 2010 to protect a handful of bats allegedly living inside. The tunnel is an engineering marvel that should be seen and experienced by humans. Opening it to trail users would help the economically depressed Western Maryland area. For example, the equally-long Blue Ridge Tunnel in Afton, Virginia, draws about 50,000 visitors annually since it was reopened in 2020.

Chesapeake & Ohio Canal National Historical Park

cumberland to little orleans

August, 2025 by aldo_desalvo

there are some really old bridges that go over the C&O. the highlight is the paw paw tunnel. better to walk through it. once you hit little orleans, i suggest going on the western maryland trail. it is fully paved and nice.
hancock is a great town

Great Allegheny Passage

Riding on this was a bucket list trail. Had hoped to ride further on it but had time restraints. Great trail. The rest stop in Meyersdale is wonderful. Plan someday to return and ride more of it.

June, 2025 by kjw979

Riding on this was a bucket list trail. Had hoped to ride further on it but had time restraints. Great trail. The rest stop in Meyersdale is wonderful. Plan someday to return and ride more of it.

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.

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

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