🔍Near me

Trails near Winter Hill, MA

1,208 trails within 30 miles of Winter Hill, for hiking, biking, horseback riding and off-road riding. Tap a trail for its map, trailhead and directions.

Hiking trails (1,139) Walking trails (1,109) Bike trails (399) Mountain bike trails (308) Paved trails (167) Horse trails (80) ATV and UTV trails (3) Dirt bike trails (8) Off-road and 4x4 trails (5) Dog-friendly trails (24) Snowmobile trails (22) Cross-country ski trails (15) Wheelchair-accessible trails (18) Rail trails (24) Greenways (16)

Quick picks

All nearby trails

Wellington Greenway

0.9 mi away

0.6 mi long · Easy · Ten Hills

Hiking Biking Paved Greenway

Clippership Connector

1.2 mi away

0.5 mi long · Easy · Medford

Hiking Biking Paved

Somerville Community Path

1.5 mi away

3.0 mi long · Easy · Somerville

Hiking Biking Paved Wheelchair accessible

Everett Riverwalk

1.9 mi away

1.1 mi long · Malden

Hiking Biking Mountain biking

Broadway

1.9 mi away

0.5 mi long · Everett

Biking Mountain biking

Methane trench

2.1 mi away

1.0 mi long · West Somerville/Davis Square

Hiking

Mystic River Path

2.1 mi away

0.6 mi long · Easy · Tufts University

Hiking Biking Paved

Alewife Brook Parkway Path

2.1 mi away

0.6 mi long · Easy · West Somerville/Davis Square

Hiking Biking Paved

Alewife Linear Park

2.2 mi away

2.1 mi long · Easy · West Somerville/Davis Square

Hiking Biking Paved

Alewife Brook Greenway

2.3 mi away

2.5 mi long · Easy · Tufts University

Hiking Biking Paved Greenway

Dr. Paul Dudley White Path

2.6 mi away

17 mi long · Easy · Dogs on leash · Lower Allston

Hiking Biking Paved Wheelchair accessible Dogs allowed

Freedom Trail

2.7 mi away

0.3 mi long · Boston National Historical Park

Hiking Wheelchair accessible

Harborwalk Charlestown

2.8 mi away

1.9 mi long · VA Boston Healthcare System, Brockton Campus

Hiking

Fresh Pond Path

2.8 mi away

2.5 mi long · Easy · North Brighton

Hiking Biking Paved

Jazz Along the Charles

3.0 mi away

0.4 mi long · Easy · Dogs allowed · Back Bay

Hiking Biking Paved Dogs allowed

Walking City Trail Section 4

3.1 mi away

6.5 mi long · Easy · Dogs allowed · Friends of the Public Garden

Hiking Paved Dogs allowed

Lagoon Path

3.2 mi away

0.5 mi long · Easy · Dogs on leash · Friends of the Public Garden

Hiking Paved Wheelchair accessible Dogs allowed

Fells Path

3.3 mi away

0.4 mi long · Easy · Melrose

Hiking Paved

Cross Fells Trail

3.3 mi away

4.6 mi long · Easy · Medford

Hiking Paved

Chelsea Greenway

3.4 mi away

0.7 mi long · Easy · Chelsea

Hiking Biking Paved Greenway

Washington-Rochambeau Revolutionary Route National Historic Trail

3.5 mi away

0.3 mi long · Easy · Boston

Hiking Paved

Boston Boundless Trail Section 1

3.5 mi away

11 mi long · Easy · Dogs allowed · South Boston

Hiking Paved Dogs allowed

Loop Trail

3.5 mi away

0.7 mi long · Winchester

Hiking Biking Mountain biking

Rock Circuit Trail

3.6 mi away

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

Hiking Dogs allowed

Ring Path

3.6 mi away

0.5 mi long · Arlington

Hiking Biking Mountain biking

Front Concrete Walkway

3.6 mi away

0.0 mi long · Easy · John Fitzgerald Kennedy National Historic Site

Hiking Paved

Southwest Side and Rear Yard Concrete Walkway

3.6 mi away

0.0 mi long · Easy · John Fitzgerald Kennedy National Historic Site

Hiking Paved

Concrete Walk to Basement

3.6 mi away

0.0 mi long · Easy · John Fitzgerald Kennedy National Historic Site

Hiking Paved

Rock Circuit Connector

3.6 mi away

0.6 mi long · Easy · Melrose

Hiking

East Boston Greenway

3.6 mi away

2.3 mi long · Easy · East Boston

Hiking Biking Paved Greenway

Melrose Path

3.7 mi away

0.4 mi long · Easy · Melrose

Hiking

Cray Trail

3.7 mi away

0.6 mi long · Melrose

Hiking

White Rock Path

3.8 mi away

0.5 mi long · Easy · Melrose

Hiking Paved

Long Pond Nature Trail

4.0 mi away

1.2 mi long · Easy · Winchester

Hiking Biking Mountain biking

South Bay Harbor Trail

4.0 mi away

0.5 mi long · Easy · Dogs on leash · South Boston

Hiking Biking Paved Wheelchair accessible Dogs allowed

Pine Grove Path

4.0 mi away

0.4 mi long · Easy · Melrose

Hiking Biking Mountain biking

Mill Creek Riverwalk

4.1 mi away

0.7 mi long · Easy · Dogs on leash · Revere

Hiking Paved Dogs allowed

Melnea Cass Bike Path

4.1 mi away

0.9 mi long · Easy · Roxbury Crossing

Biking Paved

Historic Trail

4.2 mi away

1.0 mi long · Easy · Melrose

Hiking

Virginia Wood Trail

4.2 mi away

0.4 mi long · Easy · Melrose

Hiking

Skyline Trail

4.2 mi away

7.3 mi long · Easy · Winchester

Hiking

Crystal Spring Trail

4.3 mi away

1.4 mi long · Easy · Melrose

Hiking

Tri-Community Greenway

4.3 mi away

6.5 mi long · Easy · Winchester

Hiking Biking Paved Greenway

Western Greenway

4.3 mi away

7.4 mi long · Hard · Belmont

Hiking Biking Mountain biking Greenway

Mountain Bike Loop

4.3 mi away

6.3 mi long · Easy · Winchester

Hiking Biking Mountain biking

Boston HarborWalk

4.5 mi away

29 mi long · Easy · Dogs on leash · Boston Seaport

Hiking Biking Paved Wheelchair accessible Dogs allowed

Coal Road

4.5 mi away

0.8 mi long · Easy · Belmont

Hiking Biking Mountain biking

Highland Farm Loop

4.5 mi away

0.7 mi long · No dogs · Belmont

Hiking

South Bay Harbor Trail

4.6 mi away

2.5 mi long · Easy · Dogs on leash · South Boston

Hiking Biking Paved Wheelchair accessible Dogs allowed

Watertown-Cambridge Greenway

4.6 mi away

2.7 mi long · Easy · Faneuil

Hiking Biking Paved Greenway

Northern Strand Community Trail

4.6 mi away

12 mi long · Easy · Saugus

Hiking Biking Paved

Willow Spring Path

4.8 mi away

0.6 mi long · Winchester

Hiking

orange trail

4.8 mi away

0.2 mi long · Easy · Melrose

Hiking Paved

blue trail

4.9 mi away

0.3 mi long · Easy · Melrose

Hiking Paved

Whip Hill Path

4.9 mi away

0.9 mi long · Easy · Melrose

Hiking Biking Paved

Reservoir Trail

4.9 mi away

5.9 mi long · Easy · Winchester

Hiking Biking Mountain biking

Dark Hollow Pond Trail

5.0 mi away

0.9 mi long · Easy · Stoneham

Hiking

Watertown Community Path

5.0 mi away

0.7 mi long · Easy · Watertown

Hiking Biking Paved

Conservation Trail (green)

5.1 mi away

0.7 mi long · Moderate · Arlington

Hiking Biking Mountain biking

Whipple Hill Locke Farm Loop

5.2 mi away

2.9 mi long · Easy · Arlington

Hiking Biking Mountain biking

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Nearby cities

All trails in Massachusetts

Common questions

How many trails are near Winter Hill?
We list 1,208 trails within 30 miles of Winter Hill, Massachusetts. This page shows the 60 closest.
What is the longest trail near Winter Hill?
Boston HarborWalk is the longest on this page at about 29 miles, 4.5 miles from Winter Hill.
Are there dog-friendly trails near Winter Hill?
Yes. Map data lists 10 trails on this page as open to dogs, including Dr. Paul Dudley White Path, Jazz Along the Charles, Walking City Trail Section 4. Most trails have no dog rule in our data yet, so check signs at the trailhead.