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Trails near Wellesley, MA

1,195 trails within 30 miles of Wellesley, for hiking, biking, horseback riding and off-road riding. Tap a trail for its map, trailhead and directions.

Hiking trails (1,131) Walking trails (1,111) Bike trails (372) Mountain bike trails (279) Paved trails (173) Horse trails (72) ATV and UTV trails (3) Dirt bike trails (3) Off-road and 4x4 trails (3) Dog-friendly trails (21) Snowmobile trails (21) Cross-country ski trails (13) Wheelchair-accessible trails (19) Rail trails (23) Greenways (19)

Quick picks

All nearby trails

Brook Path

0.2 mi away

2.0 mi long · Wellesley

Hiking Biking Mountain biking

Sudbury Aqueduct Path

0.7 mi away

1.1 mi long · Easy · Wellesley

Hiking Biking Paved

Crosstown Trail

0.9 mi away

0.6 mi long · Wellesley

Hiking Biking Mountain biking

Guernsey Path

0.9 mi away

0.8 mi long · Easy · Wellesley

Hiking Biking Mountain biking

Beard Trail

1.1 mi away

0.8 mi long · Wellesley

Hiking

Crosstown Trail

1.2 mi away

1.3 mi long · Wellesley

Hiking Biking Mountain biking

Brook Path

1.4 mi away

0.2 mi long · Easy · Wellesley

Hiking Biking Paved

Boulder Brook Reservation Trail

1.4 mi away

1.1 mi long · Wellesley

Hiking

Lake Waban Loop Trail

1.4 mi away

1.3 mi long · Wellesley

Hiking

Guensey Woodlands

1.4 mi away

0.6 mi long · Moderate · Wellesley

Hiking Biking Mountain biking

Riverside Trail

1.5 mi away

1.5 mi long · Mass DCR

Hiking

Cochituate Aqueduct Trail

1.6 mi away

0.9 mi long · Easy · Natick

Hiking Biking Paved

Centennial Park Trail

1.7 mi away

0.9 mi long · Newton Lower Falls

Hiking

Sudbury Path

1.8 mi away

1.0 mi long · Easy · Newton Lower Falls

Hiking Biking Mountain biking

Esker Trail

1.8 mi away

1.3 mi long · Wellesley

Hiking

Main Trail

2.0 mi away

1.3 mi long · Town of Natick

Hiking

Takawambpait North

2.2 mi away

0.6 mi long · Natick

Hiking

Longfellow Pond Trail

2.3 mi away

0.7 mi long · Newton Lower Falls

Hiking

Crosstown Trail

2.3 mi away

1.1 mi long · Newton Lower Falls

Hiking

Esker Trail

2.3 mi away

0.8 mi long · Newton Lower Falls

Hiking

Yellow Triangle

2.3 mi away

6.8 mi long · Moderate · Needham

Hiking Biking Paved

Lower Loop Trail

2.4 mi away

0.8 mi long · Town of Natick

Hiking

Charles River Path

2.4 mi away

0.9 mi long · Newton Lower Falls

Hiking Biking Mountain biking

Blue Trail

2.5 mi away

0.6 mi long · Needham

Biking Mountain biking

Goat Track

2.6 mi away

1.2 mi long · Weston Ski Track

Hiking Cross-country skiing

Eisenmenger Trail

2.7 mi away

1.9 mi long · Natick

Hiking

Sudbury Aqueduct Trail

2.8 mi away

0.5 mi long · Easy · Newton Upper Falls

Hiking Biking Mountain biking

Bay Colony Rail Trail

2.9 mi away

1.6 mi long · Easy · Dover

Hiking Biking Mountain biking Rail trail

Green Trail

3.1 mi away

0.5 mi long · Needham

Hiking Biking Mountain biking

Cochituate Rail Trail

3.1 mi away

3.6 mi long · Easy · Dogs on leash · Cochituate

Hiking Biking Paved Wheelchair accessible Dogs allowed Rail trail

Cochituate Aqueduct Trail

3.2 mi away

0.8 mi long · Newton Lower Falls

Hiking

Middlesex Path

3.2 mi away

0.6 mi long · Easy · Natick

Hiking Biking Paved

North Trail

3.2 mi away

0.7 mi long · Natick

Hiking

red

3.3 mi away

3.2 mi long · SVT

Hiking

Charles River Loop

3.4 mi away

1.0 mi long · Easy · Natick

Hiking Paved

Pegan Cove

3.4 mi away

0.4 mi long · Natick

Hiking

Glacial Hill Trail

3.5 mi away

1.4 mi long · Sherborn

Hiking

Unmarked Trail

3.5 mi away

0.7 mi long · Weston

Hiking

Deer Path Conservation Area

3.5 mi away

0.6 mi long · Weston

Hiking

yellow

3.8 mi away

1.0 mi long · Cochituate

Hiking

Blue

3.9 mi away

1.4 mi long · SVT

Hiking

Timothy Coolidge Hill

3.9 mi away

0.6 mi long · Town of Natick

Hiking

Blue Heron Trail

4.0 mi away

0.9 mi long · Newton Upper Falls

Hiking Biking Mountain biking

Cochituate Aqueduct Trail

4.0 mi away

1.3 mi long · Newton Upper Falls

Hiking Biking Mountain biking

Blueberry Swamp Loop

4.0 mi away

0.8 mi long · Sherborn

Hiking

Springdale Meadow Trail

4.0 mi away

0.6 mi long · Dover

Hiking Biking Mountain biking

Upper Falls Greenway

4.0 mi away

1.1 mi long · Newton Upper Falls

Biking Mountain biking Greenway

Healthy Heart Trail

4.1 mi away

1.2 mi long · Needham

Hiking Biking Mountain biking

Blue Heron Trail

4.1 mi away

0.9 mi long · Oak Hill Park

Hiking Biking Mountain biking

McKoy's Trail

4.1 mi away

0.5 mi long · Easy · Dover

Hiking Biking Horses Paved

Unmarked Trail

4.2 mi away

0.8 mi long · SVT

Hiking

Noanet Park Trail

4.4 mi away

1.7 mi long · Dover

Hiking Biking Mountain biking

Willoughby

4.5 mi away

0.5 mi long · Easy · Dover

Hiking Biking Paved

Weston Aqueduct Path

4.6 mi away

4.2 mi long · Wayland

Hiking Biking Mountain biking

Powerglide

4.6 mi away

0.8 mi long · Moderate · Westwood

Hiking Biking Mountain biking Horses

Blue Loop

4.6 mi away

1.1 mi long · No dogs · Sherborn

Hiking

Strawberry Hill Trail

4.7 mi away

1.0 mi long · Dover

Hiking Biking Mountain biking

Miller Hill Trail

4.7 mi away

1.4 mi long · Dover

Hiking

Red Loop

4.7 mi away

1.2 mi long · No dogs · Dover

Hiking

Peabody Loop

4.7 mi away

1.6 mi long · Dover

Hiking Biking Mountain biking

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Nearby cities

All trails in Massachusetts

Common questions

How many trails are near Wellesley?
We list 1,195 trails within 30 miles of Wellesley, Massachusetts. This page shows the 60 closest.
What is the longest trail near Wellesley?
Yellow Triangle is the longest on this page at about 6.8 miles, 2.3 miles from Wellesley.
Are there dog-friendly trails near Wellesley?
Yes. Map data lists 1 trail on this page as open to dogs, including Cochituate Rail Trail. Most trails have no dog rule in our data yet, so check signs at the trailhead.