Winchester, VA Dog Walking Trails and Maps

378 Reviews

Looking for the best Dog Walking trails around Winchester?

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

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Activities
Length
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Type
29 Results
Activities
Length
Surfaces
Type

Black Hill Trail

4.3 mi
State: MD
Asphalt, Dirt

Braddock Road Sidepath

10 mi
State: VA
Asphalt, Concrete

Carpendale Trail

0.8 mi
State: MD, WV
Crushed Stone

Centreville Road Sidepath

4.7 mi
State: VA
Asphalt

Chesapeake & Ohio Canal National Historical Park

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

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

Great Allegheny Passage

150 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

0.72 mi
State: MD
Asphalt

Harpers Ferry Railroad Bridge

0.14 mi
State: MD, WV
Boardwalk

Hawksbill Greenway

2 mi
State: VA
Asphalt

Herndon Parkway Sidepath

2 mi
State: VA
Concrete

Linton Hall Road Trail

5.4 mi
State: VA
Asphalt

Meadowlark Connector Trail

1.25 mi
State: VA
Asphalt

Rocky Run Stream Valley Trail

4.6 mi
State: VA
Asphalt, Crushed Stone

Stringfellow Road Sidepath

3 mi
State: VA
Asphalt, Concrete
Accordion

Sudley Manor Drive Trail

4.3 mi
State: VA
Asphalt

Unfinished Railroad Loop Trail

1.2 mi
State: VA
Dirt

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
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...
MD 4.3 mi Asphalt, Dirt
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 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
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
Following the Potomac River, the C&O Canal Towpath traverses the Chesapeake & Ohio Canal National Historical Park for 184.5 miles between Georgetown in Washington, D.C., and Cumberland, Maryland. For...
DC, MD 184.5 mi Brick, Concrete, Crushed Stone, Dirt
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
The Great Allegheny Passage (GAP) is an iconic rail-trail that runs 150 miles from Cumberland, Maryland, to Pittsburgh, Pennsylvania, and was built in partnership between state agencies and many local...
MD, PA 150 mi Asphalt, Concrete, Crushed Stone, Dirt, Gravel
The Great American Rail-Trail highlights some of the country’s most iconic landmarks, well-known geography and storied history across a 3,700-miles-plus route between Washington and Washington....
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 0.72 mi Asphalt
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
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
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
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
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
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 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
Accordion
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 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 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

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Trails by activity

Recent Trail Reviews

Great Allegheny Passage

Great Bike Trail!!!

September, 2019 by daysofourlives84

Brings back a lot of childhood memories, I was always riding my bike on this trial, started the trial in West Newton, PA!!!

Western Maryland Rail Trail

PAVED!

September, 2019 by tappindiva

I enjoyed this trail so much! I can say we road to the 12.5 mile marker and it was paved all the way through. There was slight elevation, but not enough to notice. There were signs all along the way talking about the Rail Line and also mile markers every mile. There are some decent bumps in the pavement from tree roots growing under the trail but not enough to deter riders but sure does hurt your bum if you're talking and not expecting it! All in all, a lovely paved trail and I would drive 2 hours all over again just to ride it! Fair warning, the bathrooms at the Big Pool trailhead are a little bit like walking into a gas station bathroom off the beaten path...but I survived!

Cross County Trail (VA)

Do not attempt with a road bike!

September, 2019 by terriannjma

Started at the north end and got ½ mile in before turning around. Large cobble stones, slick mud, large rocks, stair steps to bridge crossings and rocky water crossings are BAD news for road tires! Nobby mountain or gravel tires will have no problems. Don’t try without the right tired unless you want to ruin your bike crashing.

Accordion

Western Maryland Rail Trail

western MD rail trail

August, 2019 by rhon22jp

Excellent. Rode from Little Orleans to Hancock. Small area of gravel but mostly asphalt.

Great Allegheny Passage

GAP trail

August, 2019 by rhon22jp

Rode from Cumberland to Frostburg and back. Uphill climb to Frostburg but reasonable, not strenuous. Easy downhill return to Cumberland. Excellent trail conditions. Beautiful scenery. One tunnel.

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

Lucky Us

August, 2019 by sharonaevans00

Just feel so fortunate to have this available to us.

Chesapeake & Ohio Canal National Historical Park

Just finished!

August, 2019 by ah205

I just finished the (GAP/C&O) trail this past weekend and all was good. The dry couple of weeks helped a lot. Some ruts and only a few puddles, which is to be expected. Nice to see some of the new upgrades along the trail. Make sure you take extra water during these months. Sometimes the pumps don’t work. Great to see the trail patrol cyclists out riding as well.

Western Maryland Rail Trail

great ride

August, 2019 by llmoyers

It’s definitely a 5, but the mile marker is only up to 23. I enjoyed it very much. Especially viewing the mountains and going through them.

Great Allegheny Passage

This is the 4th we section of the GAP trail we've done. This time we started in Garret MD and rode to the continental divide. great ride. slight grade going to the divide but nice ride headed back. trail very well maintained..

August, 2019 by bpatch

This is the 4th we section of the GAP trail we've done. This time we started in Garret MD and rode to the continental divide. great ride. slight grade going to the divide but nice ride headed back. trail very well maintained..

Great Allegheny Passage

Bucket List

July, 2019 by ahaus

A definite on your bucket list! We rode the GAP/C&O from Pittsburgh to Georgetown. If you aren't a camper, the C&O requires thought and planning on where to stay. Riding both gives you a great perspective on different trails. When on the C&O, make sure you jump over to the Western Maryland Rail Trail for 22 miles, beautiful trail and a nice break from ruts and sticks (and turtles). Rode in late July, not many puddles.

Cub Run Stream Valley Trail

This trail is a danger to society

July, 2019 by tangierslane

The asphalt is broken every 4 feet with grass growing through it. It's only 4 feet wide. There are multiple steep slopes with little sight distance. Multiple locations with gravel out washes.

Bicyclists could not pass each other in opposite directions. Very large trees restrict bail-outs.

It has clear been abandoned by the FCPA.

Chesapeake & Ohio Canal National Historical Park

great trail needs maintenance badly in areas

July, 2019 by deborah.addy_tl

Rode the entire length a couple of times. Last time in June 2019. The first 10 miles out of Cumberland are terrible. If it has rained recently you will get muddy. When we went through it looked like they hadn't even mowed sections of it in a year. After that the trail had some rough patches but was ride-able. I would definitely not ride a rode bike on this trail, especially not with road tires. You need a bike with some suspension and some grip through this area. The Paw Paw tunnel was open when we went through, very interesting. Very rough and narrow inside the tunnel.
Don't know what you do if you meet a bicyclist coming the opposite direction inside the tunnel. Between Harper's Ferry and Brunswick they have resurfaced the trail and it was great. They need to put a ramp on the bridge to Harper's Ferry. We skip it as we don't want to leave our bikes behind and we aren't carrying fully loaded bikes up the spiral staircase. Fort Fredrick is an interesting side trip. The only reason the trail gets as a high a rating as I gave it is that there are free campsites all along the trail and historical markers. A lot of the campsites are by the Potomac river. They are very rustic just a picnic table, fire ring and Porta John. Sometimes there is a working water pump, sometime there isn't. I would suggest carrying a water filter, the water from the pumps is usually orange with iodine. They are usually quiet except for the occasional train. Along this trail you really can't get away from the occasional train. Also, bring bug spray in the summer if you are camping. You really don't need sunscreen, very seldom are you out from under the trees. There are huge trees all along the path.

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