🔍Near me

Trails near Medway, MA

1,049 trails within 30 miles of Medway, for hiking, biking, horseback riding and off-road riding. Tap a trail for its map, trailhead and directions.

Hiking trails (987) Walking trails (976) Bike trails (310) Mountain bike trails (227) Paved trails (157) Horse trails (60) Off-road and 4x4 trails (3) Dog-friendly trails (19) Snowmobile trails (21) Cross-country ski trails (10) Wheelchair-accessible trails (12) Rail trails (15) Greenways (18)

Quick picks

All nearby trails

Hoag's Woodsy Walk

2.6 mi away

0.5 mi long · Holliston

Hiking

Discovery Loop

4.6 mi away

0.8 mi long · Millis

Hiking

White Trail

4.9 mi away

7.0 mi long · Milford

Hiking Biking Mountain biking

BCT 10

5.0 mi away

20 mi long · No dogs · Walpole

Hiking

The Main Trail

5.1 mi away

1.2 mi long · Milford

Hiking Biking Mountain biking

White Trail

5.2 mi away

0.8 mi long · Holliston

Hiking Biking Mountain biking

Right Turn Clyde

5.3 mi away

0.6 mi long · Easy · Milford

Hiking Biking Mountain biking Horses

Yellow Trail

5.4 mi away

0.7 mi long · Sherborn

Hiking Biking Mountain biking Horses

Blue Trail

5.4 mi away

0.6 mi long · Holliston

Hiking Biking Mountain biking

Charles River Link Trail

5.5 mi away

2.2 mi long · Easy · Sherborn

Hiking Paved

Burial By-pass

5.5 mi away

0.9 mi long · Easy · Milford

Hiking Biking Paved

Bay Colony Rail Trail

5.6 mi away

1.3 mi long · Easy · Medfield

Hiking Biking Horses Paved Rail trail

Nemba Loop

5.8 mi away

0.7 mi long · Milford

Hiking Biking Mountain biking

Dirty Little Secret

5.8 mi away

0.9 mi long · Milford

Biking Mountain biking

Three Sisters

5.9 mi away

0.8 mi long · Milford

Hiking Biking Mountain biking

495 Rock Run

5.9 mi away

0.6 mi long · Milford

Hiking

Orange Trail - College Rock Park

6.1 mi away

0.7 mi long · Easy · Hopkinton

Hiking Biking Mountain biking Horses

Upper Charles Trail

6.2 mi away

14 mi long · Easy · Milford

Hiking Biking Paved

Powerline trail

6.2 mi away

0.7 mi long · Hopkinton

Hiking

Cart Path

6.2 mi away

0.5 mi long · Holliston

Hiking

Challenger

6.3 mi away

0.7 mi long · Milford

Hiking

Sassafras Trail

6.3 mi away

1.0 mi long · Ashland

Hiking

Orange Trail

6.3 mi away

0.7 mi long · Sherborn

Hiking Biking Mountain biking Horses

Karl Mighton Trail

6.4 mi away

0.8 mi long · Ashland

Hiking

Cornell Connection

6.6 mi away

0.5 mi long · Hopkinton

Hiking

Echo Lake Trail

6.6 mi away

0.6 mi long · Hopkinton

Hiking

Woodcliff Hills Trail

6.7 mi away

0.8 mi long · Medfield

Hiking

Misery Loves Company

6.8 mi away

0.7 mi long · Sherborn

Hiking

Hidden Meadow Trail

6.9 mi away

0.5 mi long · Sherborn

Hiking

Wilson Swamp Trail

7.0 mi away

0.8 mi long · Medfield

Hiking

Cheney Pond Trail

7.0 mi away

0.6 mi long · Medfield

Hiking

Donelly's Trail

7.1 mi away

0.9 mi long · Dover

Hiking Biking Mountain biking Horses

Warner Trail

7.2 mi away

32 mi long · No dogs · Friends of the Warner Trail

Hiking

Ridge Trail

7.2 mi away

1.0 mi long · Medfield

Hiking

Quarry Trail

7.2 mi away

0.7 mi long · Medfield

Hiking

Little Farm Pond Trail

7.3 mi away

0.7 mi long · Sherborn

Hiking

Field Trail

7.3 mi away

0.7 mi long · Ashland

Hiking

Dover Valley Trail

7.3 mi away

1.0 mi long · Dover

Hiking Biking Mountain biking Horses

Extended Day

7.4 mi away

0.5 mi long · Sherborn

Hiking

Red Loop

7.4 mi away

1.2 mi long · No dogs · Dover

Hiking

Blue Loop

7.4 mi away

1.1 mi long · No dogs · Sherborn

Hiking

White Trail

7.4 mi away

6.6 mi long · Sherborn

Hiking Biking Mountain biking

Elmwood Loop

7.5 mi away

0.9 mi long · Hopkinton

Hiking

White Trail

7.5 mi away

1.6 mi long · Medfield

Hiking Biking Mountain biking

Orange Trail

7.5 mi away

1.5 mi long · Friend of Adams Farm, Inc.

Hiking Biking Mountain biking

Pine Thrill

7.6 mi away

0.7 mi long · Sherborn

Hiking

Harwood Notch Trail

7.6 mi away

0.7 mi long · Medfield

Hiking

Blue Trail

7.7 mi away

1.7 mi long · Dover

Hiking Biking Mountain biking

Red Trail

7.7 mi away

1.9 mi long · Medfield

Hiking Biking Mountain biking

Orange Trail

7.7 mi away

0.5 mi long · Walpole

Hiking Biking Mountain biking

Peloquin Trail

7.7 mi away

0.8 mi long · Hopkinton

Hiking

Miller Hill Trail

7.7 mi away

1.4 mi long · Dover

Hiking

Cranberry Bog Trail (Blue)

7.8 mi away

1.3 mi long · Hopkinton

Hiking

Blue Trail

7.8 mi away

1.7 mi long · Westwood

Hiking Biking Mountain biking

Snow's Hill Trail

7.9 mi away

0.8 mi long · Dover

Hiking

F. Gilbert Hills Off-Highway Vehicle Loop

7.9 mi away

6.4 mi long · Massachusetts Department of Conservation and Recreation

Hiking Biking Mountain biking Dirt bikes

Legacy Farms Trail

7.9 mi away

1.1 mi long · Hopkinton

Hiking

Blueberry Swamp Loop

8.0 mi away

0.8 mi long · Sherborn

Hiking

Willoughby

8.0 mi away

0.5 mi long · Easy · Dover

Hiking Biking Paved

Wrentham State Forest East Off-Highway Motorcycle Loop

8.1 mi away

5.2 mi long · Wrentham

Hiking Biking Mountain biking Dirt bikes

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Nearby cities

All trails in Massachusetts

Common questions

How many trails are near Medway?
We list 1,049 trails within 30 miles of Medway, Massachusetts. This page shows the 60 closest.
What is the longest trail near Medway?
Warner Trail is the longest on this page at about 32 miles, 7.2 miles from Medway.
Are there dog-friendly trails near Medway?
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.