How many trails are near Holliston?

We list 1,118 trails within 30 miles of Holliston, Massachusetts. This page shows the 60 closest.

What is the longest trail near Holliston?

Upper Charles Trail is the longest on this page at about 14 miles, 4.4 miles from Holliston.

Are there dog-friendly trails near Holliston?

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 Holliston, MA

1,118 trails within 30 miles of Holliston, for hiking, biking, horseback riding and off-road riding. Tap a trail for its map, trailhead and directions.

Hiking trails (1,051) Walking trails (1,037) Bike trails (328) Mountain bike trails (246) Paved trails (156) Horse trails (67) Off-road and 4x4 trails (3) Dog-friendly trails (19) Snowmobile trails (23) Cross-country ski trails (11) Wheelchair-accessible trails (13) Rail trails (16) Greenways (18)

Quick picks

Closest: White Trail 0.8 mi, 1.0 mi away
Longest: Upper Charles Trail 14 mi, 4.4 mi away
Easy walk: White Trail 6.6 mi, 3.6 mi away
Paved: Charles River Link Trail 2.2 mi, 4.4 mi away
Mountain biking: White Trail 6.6 mi, 3.6 mi away
Horseback riding: Yellow Trail 0.7 mi, 3.4 mi away

All nearby trails

White Trail

1.0 mi away

0.8 mi long · Holliston

Hiking Biking Mountain biking

Blue Trail

1.2 mi away

0.6 mi long · Holliston

Hiking Biking Mountain biking

Hoag's Woodsy Walk

1.9 mi away

0.5 mi long · Holliston

Hiking

Cart Path

2.1 mi away

0.5 mi long · Holliston

Hiking

Sassafras Trail

2.3 mi away

1.0 mi long · Ashland

Hiking

Karl Mighton Trail

2.7 mi away

0.8 mi long · Ashland

Hiking

Field Trail

3.1 mi away

0.7 mi long · Ashland

Hiking

Hidden Meadow Trail

3.1 mi away

0.5 mi long · Sherborn

Hiking

Powerline trail

3.2 mi away

0.7 mi long · Hopkinton

Hiking

Yellow Trail

3.4 mi away

0.7 mi long · Sherborn

Hiking Biking Mountain biking Horses

Right Turn Clyde

3.5 mi away

0.6 mi long · Easy · Milford

Hiking Biking Mountain biking Horses

White Trail

3.6 mi away

6.6 mi long · Sherborn

Hiking Biking Mountain biking

Burial By-pass

3.7 mi away

0.9 mi long · Easy · Milford

Hiking Biking Paved

Orange Trail - College Rock Park

3.8 mi away

0.7 mi long · Easy · Hopkinton

Hiking Biking Mountain biking Horses

Discovery Loop

3.8 mi away

0.8 mi long · Millis

Hiking

The Main Trail

3.8 mi away

1.2 mi long · Milford

Hiking Biking Mountain biking

Cornell Connection

3.9 mi away

0.5 mi long · Hopkinton

Hiking

Peloquin Trail

3.9 mi away

0.8 mi long · Hopkinton

Hiking

Challenger

4.1 mi away

0.7 mi long · Milford

Hiking

Elmwood Loop

4.1 mi away

0.9 mi long · Hopkinton

Hiking

Echo Lake Trail

4.2 mi away

0.6 mi long · Hopkinton

Hiking

Legacy Farms Trail

4.2 mi away

1.1 mi long · Hopkinton

Hiking

White Trail

4.3 mi away

7.0 mi long · Milford

Hiking Biking Mountain biking

Misery Loves Company

4.3 mi away

0.7 mi long · Sherborn

Hiking

Charles River Link Trail

4.4 mi away

2.2 mi long · Easy · Sherborn

Hiking Paved

Cranberry Bog Trail (Blue)

4.4 mi away

1.3 mi long · Hopkinton

Hiking

Upper Charles Trail

4.4 mi away

14 mi long · Easy · Milford

Hiking Biking Paved

Nemba Loop

4.5 mi away

0.7 mi long · Milford

Hiking Biking Mountain biking

Orange Trail

4.5 mi away

0.7 mi long · Sherborn

Hiking Biking Mountain biking Horses

Three Sisters

4.5 mi away

0.8 mi long · Milford

Hiking Biking Mountain biking

Pine Thrill

4.6 mi away

0.7 mi long · Sherborn

Hiking

Extended Day

4.6 mi away

0.5 mi long · Sherborn

Hiking

Dirty Little Secret

4.7 mi away

0.9 mi long · Milford

Biking Mountain biking

495 Rock Run

4.7 mi away

0.6 mi long · Milford

Hiking

Little Farm Pond Trail

4.8 mi away

0.7 mi long · Sherborn

Hiking

Peter's Hill Path

5.1 mi away

0.7 mi long · Sherborn

Hiking

Deer Run Trail

5.1 mi away

0.6 mi long · Hopkinton

Hiking

Center School Trail

5.1 mi away

0.6 mi long · Hopkinton

Hiking

Bay Colony Rail Trail

5.2 mi away

1.3 mi long · Easy · Medfield

Hiking Biking Horses Paved Rail trail

Dudley Road Multi-Use Path

5.2 mi away

0.9 mi long · Easy · Framingham Center

Hiking Biking Paved

Center Trail

5.3 mi away

0.7 mi long · Hopkinton

Hiking Biking Mountain biking

Blueberry Swamp Loop

5.6 mi away

0.8 mi long · Sherborn

Hiking

Blue Loop

5.7 mi away

1.1 mi long · No dogs · Sherborn

Hiking

Blue Diamond

5.8 mi away

0.8 mi long · Ashland

Hiking

Berry Acres

5.8 mi away

0.7 mi long · Hopkinton

Hiking

Red Loop

5.9 mi away

1.2 mi long · No dogs · Dover

Hiking

Sudbury Aqueduct Trail

5.9 mi away

0.6 mi long · Framingham Center

Hiking

Timothy Coolidge Hill

5.9 mi away

0.6 mi long · Town of Natick

Hiking

Green Diamond

6.0 mi away

0.5 mi long · Ashland

Hiking

Yellow Diamond

6.0 mi away

0.5 mi long · Ashland

Hiking

Pipeline Trail

6.0 mi away

0.9 mi long · Hopkinton

Hiking

Bishop Condo Foot Path

6.0 mi away

1.0 mi long · Easy · Framingham

Hiking Paved

Pink Trail

6.0 mi away

0.7 mi long · Hopkinton

Hiking

Glebe Trail

6.0 mi away

0.7 mi long · Hopkinton

Hiking

Duck Pond Trail

6.0 mi away

1.3 mi long · Hopkinton

Hiking

Glacial Hill Trail

6.1 mi away

1.4 mi long · Sherborn

Hiking

Donelly's Trail

6.2 mi away

0.9 mi long · Dover

Hiking Biking Mountain biking Horses

Charles River Loop

6.2 mi away

1.0 mi long · Easy · Natick

Hiking Paved

Yellow Diamond

6.2 mi away

0.6 mi long · Ashland

Hiking Biking Mountain biking

Red Diamond

6.3 mi away

1.8 mi long · Ashland

Hiking Biking Mountain biking

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Nearby cities

All trails in Massachusetts

Common questions

How many trails are near Holliston?: We list 1,118 trails within 30 miles of Holliston, Massachusetts. This page shows the 60 closest.
What is the longest trail near Holliston?: Upper Charles Trail is the longest on this page at about 14 miles, 4.4 miles from Holliston.
Are there dog-friendly trails near Holliston?: 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.