How many trails are near Winchester?

We list 1,257 trails within 30 miles of Winchester, Massachusetts. This page shows the 60 closest.

What is the longest trail near Winchester?

Minuteman Bikeway is the longest on this page at about 10 miles, 4.5 miles from Winchester.

Are there dog-friendly trails near Winchester?

Yes. Map data lists 1 trail on this page as open to dogs, including Rock Circuit Trail. Most trails have no dog rule in our data yet, so check signs at the trailhead.

Trails near Winchester, MA

1,257 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 (1,180) Walking trails (1,149) Bike trails (424) Mountain bike trails (321) Paved trails (185) Horse trails (82) ATV and UTV trails (3) Dirt bike trails (8) Off-road and 4x4 trails (4) Dog-friendly trails (22) Snowmobile trails (24) Cross-country ski trails (14) Wheelchair-accessible trails (18) Rail trails (28) Greenways (17)

Quick picks

Closest: Tri-Community Greenway 6.5 mi, 0.1 mi away
Longest: Minuteman Bikeway 10 mi, 4.5 mi away
Easy walk: Tri-Community Greenway 6.5 mi, 0.1 mi away
Paved: Tri-Community Greenway 6.5 mi, 0.1 mi away
Dog friendly: Rock Circuit Trail 4.1 mi, 2.4 mi away
Mountain biking: Mountain Bike Loop 6.3 mi, 0.9 mi away
Horseback riding: Whispering Hill Loop 0.8 mi, 3.1 mi away

All nearby trails

Tri-Community Greenway

0.1 mi away

6.5 mi long · Easy · Winchester

Hiking Biking Paved Greenway

Long Pond Nature Trail

0.6 mi away

1.2 mi long · Easy · Winchester

Hiking Biking Mountain biking

Skyline Trail

0.8 mi away

7.3 mi long · Easy · Winchester

Hiking

Loop Trail

0.9 mi away

0.7 mi long · Winchester

Hiking Biking Mountain biking

Mountain Bike Loop

0.9 mi away

6.3 mi long · Easy · Winchester

Hiking Biking Mountain biking

Willow Spring Path

1.2 mi away

0.6 mi long · Winchester

Hiking

Reservoir Trail

1.3 mi away

5.9 mi long · Easy · Winchester

Hiking Biking Mountain biking

Dark Hollow Pond Trail

1.8 mi away

0.9 mi long · Easy · Stoneham

Hiking

Mystic River Path

2.4 mi away

0.6 mi long · Easy · Tufts University

Hiking Biking Paved

Rock Circuit Trail

2.4 mi away

4.1 mi long · Easy · Dogs on leash · Massachusetts Department of Conservation and Recreation

Hiking Dogs allowed

Conservation Trail (green)

2.5 mi away

0.7 mi long · Moderate · Arlington

Hiking Biking Mountain biking

Crystal Spring Trail

2.6 mi away

1.4 mi long · Easy · Melrose

Hiking

Historic Trail

2.6 mi away

1.0 mi long · Easy · Melrose

Hiking

Virginia Wood Trail

2.6 mi away

0.4 mi long · Easy · Melrose

Hiking

Melrose Path

2.6 mi away

0.4 mi long · Easy · Melrose

Hiking

Pine Grove Path

2.6 mi away

0.4 mi long · Easy · Melrose

Hiking Biking Mountain biking

Whip Hill Path

2.7 mi away

0.9 mi long · Easy · Melrose

Hiking Biking Paved

Whipple Hill Locke Farm Loop

2.8 mi away

2.9 mi long · Easy · Arlington

Hiking Biking Mountain biking

orange trail

2.9 mi away

0.2 mi long · Easy · Melrose

Hiking Paved

blue trail

2.9 mi away

0.3 mi long · Easy · Melrose

Hiking Paved

Rock Circuit Connector

3.0 mi away

0.6 mi long · Easy · Melrose

Hiking

White Rock Path

3.0 mi away

0.5 mi long · Easy · Melrose

Hiking Paved

Fells Path

3.0 mi away

0.4 mi long · Easy · Melrose

Hiking Paved

Cross Fells Trail

3.0 mi away

4.6 mi long · Easy · Medford

Hiking Paved

Whispering Hill Loop

3.1 mi away

0.8 mi long · Burlington

Hiking Biking Mountain biking Horses

ALC ACROSS Lexington Route C

3.2 mi away

2.5 mi long · Easy · Town of Lexington

Hiking Biking Paved

Clippership Connector

3.2 mi away

0.5 mi long · Easy · Medford

Hiking Biking Paved

Ring Path

3.3 mi away

0.5 mi long · Arlington

Hiking Biking Mountain biking

Pipeline Trail

3.6 mi away

0.7 mi long · Burlington

Hiking

Alewife Brook Greenway

3.7 mi away

2.5 mi long · Easy · Tufts University

Hiking Biking Paved Greenway

Alewife Linear Park

3.8 mi away

2.1 mi long · Easy · West Somerville/Davis Square

Hiking Biking Paved

Lower Vine Brook Loop

3.9 mi away

0.7 mi long · Lexington

Hiking

Cray Trail

3.9 mi away

0.6 mi long · Melrose

Hiking

ACROSS Lexington Route A

4.0 mi away

5.3 mi long · Hard · Lexington

Hiking Biking Paved Wheelchair accessible

Alewife Brook Parkway Path

4.0 mi away

0.6 mi long · Easy · West Somerville/Davis Square

Hiking Biking Paved

Highland Farm Loop

4.4 mi away

0.7 mi long · No dogs · Belmont

Hiking

Western Greenway

4.4 mi away

7.4 mi long · Hard · Belmont

Hiking Biking Mountain biking Greenway

Wellington Greenway

4.5 mi away

0.6 mi long · Easy · Ten Hills

Hiking Biking Paved Greenway

Methane trench

4.5 mi away

1.0 mi long · West Somerville/Davis Square

Hiking

Minuteman Bikeway

4.5 mi away

10 mi long · Easy · Town of Bedford

Hiking Biking Paved

ACROSS Lexington Route L

4.6 mi away

4.4 mi long · Easy · Lexington

Hiking Paved

Everett Riverwalk

4.7 mi away

1.1 mi long · Malden

Hiking Biking Mountain biking

Coal Road

4.7 mi away

0.8 mi long · Easy · Belmont

Hiking Biking Mountain biking

Wakefield Lynnfield Rail Trail

4.8 mi away

0.9 mi long · Easy · Wakefield

Hiking Biking Paved Rail trail

Carriage Road

4.9 mi away

0.9 mi long · Easy · Belmont

Hiking Biking Mountain biking

Fresh Pond Path

5.1 mi away

2.5 mi long · Easy · North Brighton

Hiking Biking Paved

ALB ACROSS Lexington Route B

5.1 mi away

4.4 mi long · Easy · Lexington

Hiking Paved

ACROSS Lexington Route E

5.1 mi away

4.7 mi long · Easy · Lexington

Hiking Paved

Landlocked Forest Yellow Trail

5.2 mi away

4.4 mi long · Lexington

Hiking Biking Mountain biking

Broadway

5.3 mi away

0.5 mi long · Everett

Biking Mountain biking

Official Burlington Trail

5.4 mi away

1.0 mi long · Burlington Conservation Department

Hiking

Ali-Waji

5.5 mi away

0.7 mi long · Pinehurst

Hiking Biking Mountain biking

social path

5.5 mi away

1.3 mi long · Wilmington

Hiking

Fern Trail

5.6 mi away

0.6 mi long · Easy · Saugus

Hiking

ACROSS Lexington Route H

5.6 mi away

3.8 mi long · Easy · Lexington

Hiking Paved

ACROSS Lexington Route M

5.6 mi away

2.7 mi long · Lexington

Hiking

Ash Path

5.7 mi away

1.0 mi long · Saugus

Hiking Biking Mountain biking

Milk Crate

5.8 mi away

0.7 mi long · Hard · Bedford

Hiking Biking Mountain biking

North 40 Loop

5.8 mi away

0.8 mi long · Easy · Wakefield

Hiking Paved

Somerville Community Path

5.9 mi away

3.0 mi long · Easy · Somerville

Hiking Biking Paved Wheelchair accessible

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Nearby cities

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Common questions

How many trails are near Winchester?: We list 1,257 trails within 30 miles of Winchester, Massachusetts. This page shows the 60 closest.
What is the longest trail near Winchester?: Minuteman Bikeway is the longest on this page at about 10 miles, 4.5 miles from Winchester.
Are there dog-friendly trails near Winchester?: Yes. Map data lists 1 trail on this page as open to dogs, including Rock Circuit Trail. Most trails have no dog rule in our data yet, so check signs at the trailhead.