Winchester, VA Inline Skating Trails and Maps

409 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
Surfaces
Type
17 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

Cub Run Stream Valley Trail

9.1 mi
State: VA
Asphalt

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

26.8 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 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 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 26-mile paved route that will take you through several eras of American history. You can access this trail from...
MD 26.8 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

Now, More Than Ever, Trails Matter!

During COVID-19, trails are being counted on as places where people can find solace and respite and we need your support to keep trails open and provide these critical FREE resources! Please continue to practice physical distancing and check the status of your trail before heading out!

Trails by activity

Cub Run Stream Valley Trail

VA - 9.1 miles

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,...

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 - 26.8 miles

Plan a full day (or two) for your visit to the Western Maryland Rail Trail (WMRT), a 26-mile paved route that will take you through several eras of American history. You can access this trail from...

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...

Accordion

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...

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...

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...

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...

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...

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...

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...

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...

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;...

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...

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...

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...

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...

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...

Accordion

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...

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...

Western Maryland Rail Trail

MD - 26.8 miles

Plan a full day (or two) for your visit to the Western Maryland Rail Trail (WMRT), a 26-mile paved route that will take you through several eras of American history. You can access this trail from...

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...

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...

Cub Run Stream Valley Trail

VA - 9.1 miles

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,...

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...

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;...

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...

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...

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...

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...

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...

Accordion

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...

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...

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...

Cub Run Stream Valley Trail

VA - 9.1 miles

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,...

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...

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...

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...

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...

Western Maryland Rail Trail

MD - 26.8 miles

Plan a full day (or two) for your visit to the Western Maryland Rail Trail (WMRT), a 26-mile paved route that will take you through several eras of American history. You can access this trail from...

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...

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;...

Recent Trail Reviews

Unfinished Railroad Loop Trail

nice trail

August, 2020 by bhattmayank

It’s kind of 2-3 mile if you want to go beyond. In the time of Covid it’s nice gateway to go with kids. You can take bile as well. Not all the way but good mountain bike

Great Allegheny Passage

A much improved trail - Ohiopyle to Confluence

August, 2020 by FrankJ

In my last review (very recent, and in fact, just yesterday) of this section of the Great Allegheny Passage, I complained about the very poor condition of the trail. Well, I rode this section again today just to see if it was repaired yet. Lo and behold, it was! New limestone was laid down on the entire 10+ mile length between Ohiopyle and Confluence. This made for a smooth, fantastic ride. I hope that the trail will be continually maintained like this. Congratulations and a BIG Thank You to the crews who did this work!! What a great surprise this was. The trail was fun again.

Great Allegheny Passage

Rough Trail - Ohiopyle to Confluence

August, 2020 by FrankJ

Generally a great trail. However, the section between Ohiopyle and Confluence is in dire need of repair. I don't know when the last time crushed limestone has been added to this trail, but it must have been 15 years ago. The last few years, this section has been very rough on tires. There is actually no limestone in several places, and you are riding on exposed base stone, which is very rough. Rough enough to destroy a tire if you are moving fast. On my last trip this past spring, the trail condition was still horrible. I'm hoping that the trail has been repaired by now (August 2020).

Accordion

Great Allegheny Passage

wonderful

July, 2020 by stempkajeffrey

Great for cyclists of all ages and levels. Pittsburgh to Ohiopyle was a great trip; lots of shade on a 90+ degree day made the heat not be much of an issue. Riders are very respectful with covid. Bring lots of water- water stations are hit/miss at present. A+ trail!

Great American Rail-Trail

Great ride today

July, 2020 by vlc9802

We rode this trail from Toulon to Princeville today. It was great! The path was very good. It is mostly shaded. Excellent. We stopped in Wyoming on our way back for lunch. Ate at 111 Coffee Shop. Don’t be fooled, this is NOT just a coffee shop. The lunch was delicious. And it is decorated all with bikes! Perfect for us bikers. And check out the bathroom. Cute!!! Can’t wait to do more of the route from Princeville going south.

Great Allegheny Passage

Perfect

July, 2020 by g19bon

We enjoyed riding from Ohiopyle to Connellsville. Even on a 90+ degree day , we were fine in the shade.

Great Allegheny Passage

Best bike trail on east coast

July, 2020 by marcnnicole0110

This trail is very diverse depending on which section you are doing, some sections are urban you have quaint towns and you have deep forest. Such an amazing blend of scenery, wildlife , and history.

Hawksbill Greenway

I enjoyed riding here with my family. A little crowded but if I went earlier in the morning I am sure that would have been better.

July, 2020 by tylerweaver662

I enjoyed riding here with my family. A little crowded but if I went earlier in the morning I am sure that would have been better.

Cross County Trail (VA)

I agree with others- not for road bike

June, 2020 by archibald.samantha

Too many bumps, gravels and turns. Uneven concrete. I have a very light road bike and it was too much for my gears and pedals

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

The best mixed use trail for miles....

June, 2020 by fwgj

This is my favorite trail for distance cycling. I drive 40-45 mins here from MD for the quality of surface and the lack of stress in dodging cars on roads. Too bad the C&O Trust in MD is unwilling and/or unable to pave and model their trail after the W&OD. Just beware of oblivious pedestrians with headphones. Pedestrian traffic is higher on weekends and east of Sterling based on trail proximity to towns and residential areas. Otherwise, get out and enjoy!

Chesapeake & Ohio Canal National Historical Park

Can’t wait until the resurfacing project is complete

June, 2020 by fwgj

Rode the C&O 6/14/2020 from Lock 23 to Edwards Ferry and back on trusty 2003 Gary Fisher Marlin MTB. My road bike would have been shattered to bits with the gravel, rocks and mud. Did try a small section of the resurfaced trail north of Edwards Ferry. WOW! They can’t resurface Swains Lock to Edwards Ferry fast enough for me. I’ll be making a donation to the project today, even with the COVID Shutdown. Find out more on trail status at https://www.nps.gov/choh/planyourvisit/towpath-resurfacing-project.htm

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

my local trail

June, 2020 by akuma758

At Vienna going west is less busy and less stops. I’ve done Shirlington (DC) to Vienna and it was too busy, with big intersections. When I ride during the weekday mornings there’s hardly anybody out, it’s the best time.

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