The Best Hiking in Gloucester

Looking for the best hiking in Gloucester? We've got you covered with the top trails, trips, hiking, backpacking, camping and more around Gloucester. The detailed guides, photos, and reviews are all submitted by the Outbound community.

Top hiking spots in and near Gloucester

Gloucester, Massachusetts

Gloucester Biking Loop

24.47 mi / 709 ft gain

Gloucester Biking Loop is a loop trail where you may see beautiful wildflowers located near Gloucester, Massachusetts.
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Gloucester, Massachusetts

Stage Fort Trail

1.28 mi / 82 ft gain

Stage Fort Trail is a loop trail where you may see beautiful wildflowers located near Gloucester, Massachusetts.
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Gloucester, Massachusetts

Babson Boulder, Tarr Trail and Common Road

6.52 mi / 292 ft gain

Babson Boulder, Tarr Trail and Common Road is a loop trail that takes you by a river located near Gloucester, Massachusetts.
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Gloucester, Massachusetts

Babson Reservoir Dogtown Loop Trail

1.85 mi / 157 ft gain

Babson Reservoir Dogtown Loop Trail is a loop trail that takes you by the lake located near Gloucester, Massachusetts.
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Gloucester, Massachusetts

Good Harbor Beach

1.38 mi / 30 ft gain

Good Harbor Beach is an out-and-back trail where you may see beautiful wildflowers located near Gloucester, Massachusetts.
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Gloucester, Massachusetts

Goose Cove Reservoir

1.96 mi / 138 ft gain

Goose Cove Reservoir is a loop trail that takes you past scenic surroundings located near Gloucester, Massachusetts.
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Gloucester, Massachusetts

Gloucester Breakwater

0.96 mi / 10 ft gain

Gloucester Breakwater is a loop trail that provides a good opportunity to view wildlife located near Gloucester, Massachusetts.
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Gloucester, Massachusetts

Whales Jaw Trail

1.95 mi / 144 ft gain

Whales Jaw Trail is an out-and-back trail that provides a good opportunity to view wildlife located near Gloucester, Massachusetts.
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Gloucester, Massachusetts

Ravenswood Outer Loop

4.32 mi / 361 ft gain

Ravenswood Outer Loop is a loop trail that takes you past scenic surroundings located near Gloucester, Massachusetts.
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Gloucester, Massachusetts

Fernwood Lake (Blue Trail) and Old Salem Trail Loop

3.57 mi / 190 ft gain

Fernwood Lake (Blue Trail) and Old Salem Trail Loop is a loop trail that takes you through a nice forest located near Gloucester, Massachusetts.
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Gloucester, Massachusetts

Ridge Road to Old Salem Road Loop

2.06 mi / 102 ft gain

Ridge Road to Old Salem Road Loop is a loop trail where you may see beautiful wildflowers located near Gloucester, Massachusetts.
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Gloucester, Massachusetts

Red Maple Swamp Trail

1.51 mi / 79 ft gain

Red Maple Swamp Trail is an out-and-back trail that provides a good opportunity to view wildlife located near Gloucester, Massachusetts.
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Gloucester, Massachusetts

Sunset Mountain Trail

3.15 mi / 269 ft gain

Sunset Mountain Trail is an out-and-back trail that provides a good opportunity to view wildlife located near Gloucester, Massachusetts.
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Gloucester, Massachusetts

Thompson Mountain Loop

1.3 mi / 89 ft gain

Thompson Mountain Loop is a loop trail that takes you through a nice forest located near Gloucester, Massachusetts.
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Rockport, Massachusetts

Briar Swamp Loop via Luce Trail

2.16 mi / 39 ft gain

Briar Swamp Loop via Luce Trail is a loop trail that takes you by the lake located near Rockport, Massachusetts.
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Gloucester, Massachusetts

Mount Avalon Loop

0.43 mi / 98 ft gain

Mount Avalon Loop is a loop trail that takes you through a nice forest located near Gloucester, Massachusetts.
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