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

    Ravenswood Park Trail

    2.35 mi / 197 ft gain
    Ravenswood Park Trail 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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