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Trails near Webster, MA

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

Hiking trails (726) Walking trails (715) Bike trails (173) Mountain bike trails (124) Paved trails (83) Horse trails (38) ATV and UTV trails (4) Off-road and 4x4 trails (5) Dog-friendly trails (25) Snowmobile trails (50) Cross-country ski trails (90) Wheelchair-accessible trails (6) Rail trails (6) Greenways (7)

Quick picks

All nearby trails

Frank's Trail

3.2 mi away

0.7 mi long · Dudley

Hiking

North Grosvenordale River Trail

4.1 mi away

1.3 mi long · Easy · North Grosvenor Dale

Hiking Biking Paved

Hay Ride Trail

4.7 mi away

0.8 mi long · Douglas

Hiking

Saddle Trail

5.0 mi away

0.9 mi long · Easy · Douglas

Hiking Paved

Eagle Bridge Trail

5.1 mi away

1.1 mi long · Douglas

Hiking

Grand Trunk Trail

5.2 mi away

1.0 mi long · Easy · Douglas

Paved

Pain in the Pullman

5.2 mi away

1.3 mi long · Douglas

Hiking

Schmidt Trail

5.2 mi away

1.2 mi long · Douglas

Southern New England Railway

5.3 mi away

1.6 mi long · Southbridge

Hiking

Stud Finder

5.3 mi away

1.2 mi long · Douglas

Hiking

Streeter Trail

5.6 mi away

0.7 mi long · Easy · Douglas

Hiking Biking Horses Paved

Buck Hill Yellow Dot

5.6 mi away

1.4 mi long · Douglas

Hiking Biking Mountain biking Horses

Border Trail

6.0 mi away

1.4 mi long · Thompson

Hiking Biking Mountain biking

Wallum Lake Overlook

6.0 mi away

0.5 mi long · Easy · Douglas

Hiking Paved

Grand Trunk Trail

6.0 mi away

0.8 mi long · Easy · Douglas

Paved

Ravenelle Ponds Loop

6.1 mi away

1.5 mi long · United States Army Corps of Engineers

Hiking Biking Mountain biking

Midstate Trail

6.1 mi away

93 mi long · Easy · Paxton

Hiking

Benson Mountain Trail

6.3 mi away

3.5 mi long · Douglas

Hiking

Lost Trail

6.3 mi away

1.2 mi long · United States Army Corps of Engineers

Hiking Biking Mountain biking

Outer Loop Trail

6.4 mi away

1.2 mi long · Wyndham Land Trust

Hiking Biking Mountain biking

Loop Trail

6.5 mi away

0.6 mi long · Wyndham Land Trust

Hiking Biking Mountain biking

Woodland Walk Trail

6.6 mi away

0.5 mi long · United States Army Corps of Engineers

Hiking Biking Mountain biking

Viewpoint Trail

6.7 mi away

0.6 mi long · Easy · Wyndham Land Trust

Hiking Biking Paved

Titanic Rail Trail

6.7 mi away

11 mi long · Town of Dudley

Hiking Biking Mountain biking Rail trail

Quinebaug Valley Rail Trail

6.7 mi away

2.0 mi long · Easy · Town of Southbridge

Hiking Biking Paved Rail trail

Blue Trail

7.0 mi away

0.6 mi long · Dogs on leash · Opacum Land Trust

Hiking Biking Mountain biking Dogs allowed

Buck Hill Point Trail

7.1 mi away

0.7 mi long · Douglas

Hiking Horses

Shoreline Trail

7.3 mi away

4.3 mi long · United States Army Corps of Engineers

Hiking Biking Mountain biking

Quaddick Trail

7.3 mi away

1.4 mi long · Thompson

Hiking

Quinebaug River Trail

7.3 mi away

5.8 mi long · United States Army Corps of Engineers

Hiking Biking Mountain biking

Air Line Trail

7.6 mi away

57 mi long · Easy · Town of Thompson

Hiking Biking Horses Paved

Wabbaquasset Trail

7.7 mi away

1.1 mi long · Southbridge

Hiking

Wilson Trail

7.9 mi away

0.7 mi long · Pascoag

Munyon Trail

7.9 mi away

1.4 mi long · Thompson

Wilson Trail

8.0 mi away

1.0 mi long · Pascoag

Border/Munyon Connector

8.4 mi away

0.8 mi long · Thompson

Joe's Trail

8.4 mi away

1.7 mi long · Sutton

Hiking Biking Mountain biking

Border Trail

8.6 mi away

2.6 mi long · Thompson

The Mistress

8.8 mi away

1.4 mi long · Sutton

Hiking

Par 5

8.8 mi away

3.9 mi long · Sutton

Hiking

Inner Border Trail

8.9 mi away

1.3 mi long · Thompson

Low Roller

8.9 mi away

1.4 mi long · Sutton

Hiking

Putnam River Trail

8.9 mi away

2.2 mi long · Easy · Putnam

Hiking Biking Paved

Green

9.0 mi away

0.7 mi long · Tree House Brewing Company

Hiking

Haze

9.0 mi away

0.7 mi long · Tree House Brewing Company

Hiking

Very Hazy

9.0 mi away

0.5 mi long · Tree House Brewing Company

Hiking

Julius

9.0 mi away

0.5 mi long · Tree House Brewing Company

Hiking

Richardson Trail

9.0 mi away

1.2 mi long · Pascoag

Thompson Loop Trail

9.2 mi away

1.0 mi long · Dogs on leash · Opacum Land Trust

Hiking Dogs allowed

George Washington Orange Trail

9.2 mi away

2.5 mi long · Thompson

Hiking

Blue Dot

9.3 mi away

1.3 mi long · Thompson

Hiking

Westville Lake Trail

9.4 mi away

0.7 mi long · Southbridge

Hiking Biking Mountain biking

Center Trail

9.5 mi away

3.3 mi long · Pascoag

George Washington Orange Trail

9.5 mi away

2.8 mi long · Pascoag

Hiking Biking Mountain biking

Rose of Sharons Way

9.9 mi away

0.6 mi long · Millbury

Hiking

Old Common Road Trail

9.9 mi away

0.7 mi long · Millbury

Hiking

yellow trail

10 mi away

0.5 mi long · Auburn

Hiking

Old Purgatory Trail

10 mi away

0.6 mi long · Massachusetts Department of Conservation and Recreation

Hiking

Ross Trail

10 mi away

1.2 mi long · Pascoag

Charley's Loop Trail

10 mi away

1.0 mi long · Massachusetts Department of Conservation and Recreation

Hiking Cross-country skiing

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Nearby cities

All trails in Massachusetts

Common questions

How many trails are near Webster?
We list 752 trails within 30 miles of Webster, Massachusetts. This page shows the 60 closest.
What is the longest trail near Webster?
Midstate Trail is the longest on this page at about 93 miles, 6.1 miles from Webster.
Are there dog-friendly trails near Webster?
Yes. Map data lists 2 trails on this page as open to dogs, including Blue Trail, Thompson Loop Trail. Most trails have no dog rule in our data yet, so check signs at the trailhead.