Winchester Inline Skating Trails and Maps

339 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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  • Length
Activities
Length
Surfaces
Type
16 Results
Activities
Length
Surfaces
Type

Braddock Road Sidepath

10 mi
State: VA
Asphalt, Concrete

Centreville Road Sidepath

4.7 mi
State: VA
Asphalt

Cross County Trail (VA)

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

Fairfax County Parkway Trail

28.3 mi
State: VA
Asphalt

Folly Lick Branch Trail

2 mi
State: VA
Asphalt

H & F Trolley Trail

0.72 mi
State: MD
Asphalt

Linton Hall Road Trail

5.4 mi
State: VA
Asphalt

Meadowlark Connector Trail

1.25 mi
State: VA
Asphalt

Sudley Manor Drive Trail

4.3 mi
State: VA
Asphalt

WV Route 9 Bike Path

10 mi
State: WV
Asphalt

Warrenton Branch Greenway

2 mi
State: VA
Asphalt

West Ox Road Sidepath

2.9 mi
State: VA
Asphalt

Western Maryland Rail Trail

22 mi
State: MD
Asphalt

White's Mill Trail

1.3 mi
State: VA
Asphalt

Winchester Green Circle

5.3 mi
State: VA
Asphalt
Trail Image Trail Name States Length Surface Rating
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
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 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...
VA 40 mi Asphalt, Ballast, Concrete, Crushed Stone, Dirt, Gravel
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 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
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 0.72 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
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
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...
WV 10 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 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...
VA 45 mi Asphalt, Concrete
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
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...
MD 22 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
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

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Trails by activity

Linton Hall Road Trail

VA - 5.4 miles

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...

Cross County Trail (VA)

VA - 40 miles

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...

H & F Trolley Trail

MD - 0.72 miles

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...

Winchester Green Circle

VA - 5.3 miles

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...

Accordion

White's Mill Trail

VA - 1.3 miles

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...

Western Maryland Rail Trail

MD - 22 miles

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...

Fairfax County Parkway Trail

VA - 28.3 miles

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...

Centreville Road Sidepath

VA - 4.7 miles

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...

Sudley Manor Drive Trail

VA - 4.3 miles

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...

WV Route 9 Bike Path

WV - 10 miles

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...

Warrenton Branch Greenway

VA - 2 miles

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...

Meadowlark Connector Trail

VA - 1.25 miles

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;...

West Ox Road Sidepath

VA - 2.9 miles

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...

Braddock Road Sidepath

VA - 10 miles

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...

Folly Lick Branch Trail

VA - 2 miles

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...

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

VA - 45 miles

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...

Folly Lick Branch Trail

VA - 2 miles

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...

Linton Hall Road Trail

VA - 5.4 miles

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...

Fairfax County Parkway Trail

VA - 28.3 miles

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...

West Ox Road Sidepath

VA - 2.9 miles

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...

Accordion

Winchester Green Circle

VA - 5.3 miles

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...

Sudley Manor Drive Trail

VA - 4.3 miles

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...

H & F Trolley Trail

MD - 0.72 miles

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...

Cross County Trail (VA)

VA - 40 miles

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...

Braddock Road Sidepath

VA - 10 miles

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...

White's Mill Trail

VA - 1.3 miles

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...

Centreville Road Sidepath

VA - 4.7 miles

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...

WV Route 9 Bike Path

WV - 10 miles

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...

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

VA - 45 miles

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...

Meadowlark Connector Trail

VA - 1.25 miles

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;...

Western Maryland Rail Trail

MD - 22 miles

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...

Warrenton Branch Greenway

VA - 2 miles

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...

Linton Hall Road Trail

VA - 5.4 miles

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...

WV Route 9 Bike Path

WV - 10 miles

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...

Folly Lick Branch Trail

VA - 2 miles

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...

West Ox Road Sidepath

VA - 2.9 miles

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...

Accordion

Meadowlark Connector Trail

VA - 1.25 miles

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;...

White's Mill Trail

VA - 1.3 miles

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...

H & F Trolley Trail

MD - 0.72 miles

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...

Centreville Road Sidepath

VA - 4.7 miles

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...

Winchester Green Circle

VA - 5.3 miles

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...

Fairfax County Parkway Trail

VA - 28.3 miles

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...

Warrenton Branch Greenway

VA - 2 miles

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...

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

VA - 45 miles

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...

Sudley Manor Drive Trail

VA - 4.3 miles

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...

Western Maryland Rail Trail

MD - 22 miles

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...

Cross County Trail (VA)

VA - 40 miles

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...

Braddock Road Sidepath

VA - 10 miles

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...

Recent Trail Reviews

Warrenton Branch Greenway

Great community asset!

May, 2018 by laurastark

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.

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

Nice trail! Well paved & marked.

May, 2018 by opstadp

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!

Western Maryland Rail Trail

clean, paved trail with a little bit of history.

April, 2018 by amosonu

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.

Accordion

Cross County Trail (VA)

Not for Road Bikes

April, 2018 by dgoosbey2

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.

Western Maryland Rail Trail

One of my favorites

February, 2018 by beckyaboardsvanteris

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.

Great Allegheny Passage

Allegheny/ CO Labor Day

December, 2017 by mmblhb

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.

Great Allegheny Passage

Can't wait to do this again!

October, 2017 by aeboe

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!

WV Route 9 Bike Path

We Loved It!

October, 2017 by hummelr

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.

Great Allegheny Passage

serene and calm

October, 2017 by bicycle67

Great trail for multi-day ride with motels or camping, or single day rides. I had to find parking locations in order to ride several days, with Round trip rides of 40-60 miles/day (20-30 each way). A few confusing spots and a couple steep spots. Quite confusing in Pittsburgh, where markings are absent, and trail goes through the city streets, but lovely to arrive at Point State Park fountain. Cedar Creek Park especially lovely area, with camping (but gates lock at sundown so don't park late). Great long ride down gentle hill from Deal, MD (highest point on trail) to Cumberland. Long uphill ride back up 26 miles from Cumberland back to Deal. Beautiful trail.

WV Route 9 Bike Path

Far from peaceful

September, 2017 by scott_music

From hundreds of cars to the overhead planes landing at a nearby airport, this trail was full of urban noise. The challenging hills, the asphalt trail and the geocaches were a plus but, for me, prefer a trail more serene.

Western Maryland Rail Trail

Just far enough from the cities!

September, 2017 by rmjonesjr

This wonderful trail is just far enough from the heavily populated Baltimore/Washington area that it is never crowded. Even on "busy" weekends you'll pass just a few other friendly folks who enjoy biking enough to make the trek to Hancock. For us "weird" recumbent trike riders there are a few teeth rattling tree roots pushing up the asphalt in places. Regular bikes with even modest suspension or fat tires will barely notice them. Enjoy this wonderful gem of a trail!

WV Route 9 Bike Path

omega3jane

September, 2017 by omega3jane

I have ridden this path several times. There are many hills and some come straight down to a stop to cross the road. After which, you then pedal straight up hill. However, the path is quite do-able. There are two treats for you on this ride - 1) a stop at Black Dog Coffee and at the Martinsburg end, you can cross the highway (carefully) to find the Berkeley County Human Society and visit with the pooches! Enjoy and cycle safe!

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