How many trails are near Winchester?

We list 441 trails within 30 miles of Winchester, Virginia. This page shows the 60 closest.

What is the longest trail near Winchester?

Sky Meadows State Park is the longest on this page at about 8.9 miles, 18 miles from Winchester.

Are there dog-friendly trails near Winchester?

None of the trails on this page have a dog rule in our data yet. Check signs at the trailhead or the park's website.

Trails near Winchester, VA

441 trails within 30 miles of Winchester, for hiking, biking, horseback riding and off-road riding. Tap a trail for its map, trailhead and directions.

Hiking trails (409) Walking trails (379) Bike trails (217) Mountain bike trails (203) Paved trails (38) Horse trails (135) ATV and UTV trails (4) Off-road and 4x4 trails (5) Dog-friendly trails (10) Snowmobile trails (10) Cross-country ski trails (27) Wheelchair-accessible trails (16) Rail trails (7) Greenways (21)

Quick picks

Closest: Sycamore Trail 0.6 mi, 0.9 mi away
Longest: Sky Meadows State Park 8.9 mi, 18 mi away
Easy walk: Kiwanis Parcourse (Fitness Trail) 1.0 mi, 1.0 mi away
Paved: Green Circle Trail 3.2 mi, 0.9 mi away
Mountain biking: Perimeter Trail 3.0 mi, 18 mi away
Horseback riding: Historic Packhorse Trail 0.9 mi, 14 mi away

All nearby trails

Sycamore Trail

0.9 mi away

0.6 mi long · Winchester

Hiking

Green Circle Trail

0.9 mi away

3.2 mi long · Easy · Winchester

Biking Paved

Kiwanis Parcourse (Fitness Trail)

1.0 mi away

1.0 mi long · Easy · Winchester

Hiking Biking Paved

Third Battle of Winchester Trail

1.8 mi away

0.6 mi long · Winchester

Hiking Biking Mountain biking

Snowden walking path

4.5 mi away

0.6 mi long · Easy · Winchester

Hiking Paved

Bowman Lake Trail

6.0 mi away

0.5 mi long · Frederick County Parks and Recreation

Hiking

Sherando Park Mountain Bike Trail G (Long Path)

7.0 mi away

1.3 mi long · Stephens City

Biking Mountain biking

Sherando Park Mountain Bike Trail F

7.1 mi away

1.4 mi long · Stephens City

Biking Mountain biking

Walking path

8.9 mi away

1.7 mi long · Easy · Shawnee Land

Hiking Paved

Lake Frederick Hiking Trail

9.9 mi away

7.7 mi long · Stephens City

Hiking

Native Plant Trail

10 mi away

0.7 mi long · Shenandoah Farms

Hiking

Pangleton Trail

10 mi away

1.2 mi long · Shawnee Land

Biby Wilderness Trail

11 mi away

0.6 mi long · Shawnee Land

Hiking

Orange Trail

12 mi away

0.7 mi long · Shawnee Land

Hiking

Red Trail

12 mi away

1.4 mi long · Shawnee Land

Hiking

Linda's Loop

13 mi away

1.2 mi long · Charles Town

Hiking

Chipmunk Trail

14 mi away

1.6 mi long · Shawnee Land

Tuscarora Trail

14 mi away

0.6 mi long · Inwood

Hiking

Historic Packhorse Trail

14 mi away

0.9 mi long · Inwood

Horses

Hayes-Ramseur Loop Trail

14 mi away

0.5 mi long · Middletown

Hiking

Thomas' Brigade Loop Trail

14 mi away

0.7 mi long · Middletown

Hiking

Vermont Monument Trail

14 mi away

0.1 mi long · Middletown

19th Corps Trail

14 mi away

1.3 mi long · Middletown

Hiking

Mill Race Trail (yellow)

14 mi away

1.4 mi long · Inwood

Hiking Biking Mountain biking

Tuscarora Trail

15 mi away

3.7 mi long · Inwood

Hiking

Tuscarora Trail (Slickee Blur)

15 mi away

1.4 mi long · Inwood

Hiking Biking Mountain biking

Pee Wee Point Trail

16 mi away

2.0 mi long · Inwood

Ambassador Whitehouse Trail

16 mi away

1.1 mi long · Shenandoah Farms

Hiking

Old Trail

16 mi away

1.9 mi long · Shenandoah Farms

Hiking

South Ridge Trail

16 mi away

1.7 mi long · Shenandoah Farms

Hiking

Ridge to River Trail

16 mi away

1.3 mi long · Rolling Ridge Conservancy

Hiking Biking Mountain biking

Gap Run Trail

17 mi away

0.7 mi long · Shenandoah Farms

Hiking

Perimeter Trail

17 mi away

1.9 mi long · Rolling Ridge Conservancy

Hiking Biking Mountain biking

James Ball Trail

17 mi away

0.8 mi long · Shenandoah Farms

Hiking

Piedmont Overlook Trail

17 mi away

0.6 mi long · Shenandoah Farms

Hiking

Boston Mill Road Trail

17 mi away

0.5 mi long · Easy · Shenandoah Farms

Hiking Biking Horses Paved

North Ridge Trail

17 mi away

1.7 mi long · Shenandoah Farms

Hiking

Hadow Trail

17 mi away

0.7 mi long · Shenandoah Farms

Hiking

Ridge to River / Perimeter Trail

17 mi away

0.5 mi long · Rolling Ridge Conservancy

Hiking Biking Mountain biking

Snowden Trail

17 mi away

1.1 mi long · Shenandoah Farms

Hiking

Niles Cabin Trail

17 mi away

0.7 mi long · Rolling Ridge Conservancy

Hiking Biking Mountain biking

Ridge to River / Perimeter / Power Line Trail

17 mi away

0.6 mi long · Rolling Ridge Conservancy

Hiking Biking Mountain biking

Sensory Explorer's Trail

17 mi away

0.3 mi long · Shenandoah Farms

Hiking

Sky Meadows State Park

18 mi away

8.9 mi long · Easy · Shenandoah Farms

Hiking Horses Paved

Tribute Trail

18 mi away

0.4 mi long · Shenandoah Farms

Hiking

Tuscarora Trail (Blue)

18 mi away

0.6 mi long · Inwood

Hiking

TRACK Trail

18 mi away

0.6 mi long · Shenandoah Farms

Hiking

Corporal Morgan Trail

18 mi away

1.5 mi long · Shenandoah Farms

Hiking

Hayfield Trail

18 mi away

0.8 mi long · Easy · Virginia Department of Conservation and Recreation

Hiking Biking Horses Paved

Strasburg Trail

18 mi away

0.9 mi long · Strasburg

Hiking Biking Mountain biking

Friends Trail

18 mi away

1.0 mi long · Rolling Ridge Conservancy

Hiking

Perimeter Trail

18 mi away

3.0 mi long · Rolling Ridge Conservancy

Hiking Biking Mountain biking

Trico Tower Trail

18 mi away

0.5 mi long · Shenandoah Farms

Hiking

Langdon Loop

18 mi away

0.5 mi long · Shannondale

Hiking Biking Mountain biking

Rolling Meadows Trail

18 mi away

2.4 mi long · Easy · Virginia Department of Conservation and Recreation

Hiking Biking Horses Paved

Old Pasture Trail

18 mi away

0.6 mi long · Easy · Virginia Department of Conservation and Recreation

Hiking Biking Horses Paved

Old Romney Grade Jeep Trail

18 mi away

4.3 mi long · Shawnee Land

Shermans Mill Trail

18 mi away

1.0 mi long · Shenandoah Farms

Hiking

Lost Mountain Trail

18 mi away

1.8 mi long · Virginia Department of Conservation and Recreation

Hiking Horses

Washington's Ridge Trail

18 mi away

0.6 mi long · Virginia Department of Conservation and Recreation

Hiking Horses

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Nearby cities

All trails in Virginia

Common questions

How many trails are near Winchester?: We list 441 trails within 30 miles of Winchester, Virginia. This page shows the 60 closest.
What is the longest trail near Winchester?: Sky Meadows State Park is the longest on this page at about 8.9 miles, 18 miles from Winchester.
Are there dog-friendly trails near Winchester?: None of the trails on this page have a dog rule in our data yet. Check signs at the trailhead or the park's website.