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Trails near Gloucester, MA

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

Hiking trails (361) Walking trails (339) Bike trails (177) Mountain bike trails (118) Paved trails (84) Horse trails (21) ATV and UTV trails (6) Dirt bike trails (6) Off-road and 4x4 trails (17) Dog-friendly trails (16) Snowmobile trails (71) Cross-country ski trails (3) Wheelchair-accessible trails (12) Rail trails (12) Greenways (10)

Quick picks

All nearby trails

Ledge Hill Trail (Orange)

1.6 mi away

1.1 mi long · Gloucester

Hiking Biking Mountain biking

Babson Boulder Trail

1.8 mi away

0.7 mi long · Gloucester

Hiking Biking Mountain biking Horses

Moraine Trail

1.9 mi away

0.8 mi long · Gloucester

Hiking Biking Mountain biking Horses

Art's Trail

1.9 mi away

0.8 mi long · Rockport

Hiking Biking Mountain biking Horses

Ted Nugent

2.0 mi away

0.7 mi long · Rockport

Hiking

Fernwood Lake Trail (Blue)

2.1 mi away

1.8 mi long · Gloucester

Hiking Biking Mountain biking

Boulder Field Trail (Red)

2.2 mi away

0.6 mi long · Gloucester

Hiking

Frontline

2.2 mi away

0.6 mi long · Rockport

Hiking

Susan's Point

2.2 mi away

0.5 mi long · Gloucester

Hiking

Magnolia Swamp Trail (Yellow)

2.3 mi away

1.1 mi long · Easy · Gloucester

Hiking

Coyote

2.4 mi away

1.3 mi long · Rockport

Hiking

Spiderman

2.4 mi away

1.2 mi long · Rockport

Hiking

Captain Nemo

2.5 mi away

0.7 mi long · Rockport

Hiking

Granite Top

2.5 mi away

0.7 mi long · Gloucester

Hiking Biking Mountain biking

Mongrel

2.5 mi away

0.5 mi long · Rockport

Hiking

Nellie's Trail

2.6 mi away

0.9 mi long · Rockport

Hiking Biking Mountain biking Horses

Wallace Drop In

2.6 mi away

0.7 mi long · Gloucester

Hiking Biking Mountain biking

Tarr Trail

2.7 mi away

1.1 mi long · Rockport

Hiking Biking Mountain biking Horses

Pipeline

2.7 mi away

0.7 mi long · Rockport

Hiking

Dinosaur

2.9 mi away

0.5 mi long · Rockport

Hiking Biking Mountain biking Horses

Polaris

3.0 mi away

0.9 mi long · Gloucester

Hiking

Yellow Trail

3.0 mi away

0.7 mi long · Gloucester

Hiking

ManBearPig

3.2 mi away

0.5 mi long · Rockport

Hiking

Passing Gas

3.2 mi away

0.9 mi long · Essex

Hiking

NHL

3.3 mi away

0.8 mi long · Rockport

Hiking

Black Coffee

3.4 mi away

0.6 mi long · Manchester-by-the-Sea

Hiking Biking Mountain biking

4x4 trail

3.8 mi away

0.7 mi long · Essex

Hiking

Bad Dog

3.9 mi away

0.7 mi long · Rockport

Hiking

Stoneman

4.1 mi away

0.7 mi long · Manchester-by-the-Sea

Hiking

NSA

4.2 mi away

0.8 mi long · Manchester-by-the-Sea

Hiking

4x4 Ledge Trails

4.2 mi away

1.3 mi long · Essex

Hiking

4x4 trail

4.2 mi away

0.6 mi long · Essex

Hiking

Hooper-Trask

4.2 mi away

0.5 mi long · Manchester-by-the-Sea

Hiking

Resdawg

4.4 mi away

1.7 mi long · Hard · Manchester-by-the-Sea

Hiking Biking Mountain biking

Stupid Trail

4.4 mi away

0.9 mi long · Hard · Manchester-by-the-Sea

Hiking Biking Mountain biking

4x4 trail

4.5 mi away

1.5 mi long · Essex

Hiking

Old Rail Track

4.5 mi away

1.1 mi long · Rockport

Hiking

Bandidos

4.6 mi away

0.6 mi long · Hard · Essex

Hiking Biking Mountain biking

Cliffhanger

4.7 mi away

1.2 mi long · Manchester-by-the-Sea

Hiking

Fishbone

4.7 mi away

1.2 mi long · Hard · Essex

Hiking Biking Mountain biking

Tombstone

4.7 mi away

1.1 mi long · Hard · Manchester-by-the-Sea

Hiking Biking Mountain biking

The Gloucester Spot

4.8 mi away

1.8 mi long · Hard · Manchester-by-the-Sea

Hiking Biking Mountain biking

Stu & Erin's

4.9 mi away

0.8 mi long · Hard · Manchester-by-the-Sea

Hiking Biking Mountain biking

Dark Tower

5.0 mi away

0.6 mi long · Hard · Manchester-by-the-Sea

Hiking Biking Mountain biking

Charlie Trail

5.2 mi away

0.6 mi long · Manchester-by-the-Sea

Hiking

Atlantic Path

5.5 mi away

0.6 mi long · Rockport

Hiking

Cedar Swamp Trail

5.8 mi away

1.0 mi long · Manchester-by-the-Sea

Hiking

Yellow Trail

5.9 mi away

0.7 mi long · The Trustees of Reservations

Hiking

Prospect Ledge Trail

5.9 mi away

1.9 mi long · Manchester-by-the-Sea

Hiking

Homestead Trail

6.0 mi away

0.8 mi long · Essex

Hiking Biking Mountain biking

Pulpit Rock

6.2 mi away

0.8 mi long · Manchester-by-the-Sea

Hiking Biking Mountain biking

Sesame Street Trail

6.3 mi away

1.2 mi long · Essex

Hiking Biking Mountain biking

Cheever Commons Loop

6.5 mi away

0.6 mi long · Manchester-by-the-Sea

Hiking Biking Mountain biking

Ancient Line Trail

6.5 mi away

1.5 mi long · Manchester-by-the-Sea

Hiking

Red Trail

6.6 mi away

1.8 mi long · The Trustees of Reservations

Hiking

Green Trail

6.6 mi away

1.6 mi long · Essex

Hiking

Bishop's Grave Cartway

6.6 mi away

1.6 mi long · Essex

Hiking Biking Mountain biking

Skirt

6.8 mi away

0.6 mi long · Manchester-by-the-Sea

Hiking

Gas Line

6.8 mi away

0.8 mi long · Essex

Hiking

Dug Hill Trail

7.1 mi away

0.5 mi long · Moderate · Manchester-by-the-Sea

Hiking Biking Mountain biking

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Nearby cities

All trails in Massachusetts

Common questions

How many trails are near Gloucester?
We list 403 trails within 30 miles of Gloucester, Massachusetts. This page shows the 60 closest.
What is the longest trail near Gloucester?
Prospect Ledge Trail is the longest on this page at about 1.9 miles, 5.9 miles from Gloucester.
Are there dog-friendly trails near Gloucester?
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.