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The Best Hiking in Richmond

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

Top hiking spots in and near Richmond

  • West Stockbridge, Massachusetts

    Stevens Glen Trail

    1 mi / 249 ft gain
    Stevens Glen Trail is a loop trail that takes you by a waterfall located near West Stockbridge, Massachusetts.
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  • West Stockbridge, Massachusetts

    Olivia's Overlook Via Charcoal Trail

    1.74 mi / 489 ft gain
    Olivia's Overlook Via Charcoal Trail is a loop trail that is moderately difficult located near Richmond, Massachusetts.
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  • Richmond, Massachusetts

    Burbank Trail

    2.98 mi / 482 ft gain
    Burbank Trail is a loop trail where you may see beautiful wildflowers located near Richmond, Massachusetts.
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  • Lenox, Massachusetts

    Trail of the Ledges and Overbrook Trail

    2.56 mi / 879 ft gain
    Trail of the Ledges and Overbrook Trail is a loop trail where you may see beautiful wildflowers located near Lenox, Massachusetts.
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  • Pittsfield, Massachusetts

    Shaker Mountain Loop via Shaker Trail

    5.19 mi / 1027 ft gain
    Shaker Mountain Loop via Shaker Trail is a loop trail that takes you by the lake located near Pittsfield, Massachusetts.
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  • Pittsfield, Massachusetts

    Shaker Mountain (Short Option)

    3.17 mi / 774 ft gain
    Shaker Mountain (Short Option) is an out-and-back trail that takes you by a lake located near Pittsfield, Massachusetts.
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  • Pittsfield, Massachusetts

    Holy Mount via Shaker Trail

    6.64 mi / 1302 ft gain
    Holy Mount via Shaker Trail is an out-and-back trail that takes you through a nice forest located near Pittsfield, Massachusetts.
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  • Austerlitz, New York

    Harvey Mountain and Pinnacle Point Loop

    4.33 mi / 748 ft gain
    Harvey Mountain and Pinnacle Point Loop is a loop trail where you may see local wildlife located near Austerlitz, New York.
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  • Austerlitz, New York

    Harvey Mountain Trail

    3.16 mi / 630 ft gain
    Harvey Mountain Trail is an out-and-back trail where you may see beautiful wildflowers located near Austerlitz, New York.
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  • Chatham, New York

    Beebe Hill

    1.61 mi / 308 ft gain
    Beebe Hill is an out-and-back trail that is good for all skill levels located near East Chatham, New York.
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  • Canaan, New York

    Green Trail Loop to Red Trail

    1.94 mi / 433 ft gain
    Green Trail Loop to Red Trail is a loop trail that takes you by a lake located near East Chatham, New York.
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  • Lenox, Massachusetts

    October Mountain Loop

    6.69 mi / 1401 ft gain
    October Mountain Loop is a loop trail that takes you by the lake located near Lee, Massachusetts.
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  • Stockbridge, Massachusetts

    Laura's Tower and Ice Glen

    5.0
    2.4 mi / 676 ft gain
    You will park at the end of Park Street in Stockbridge, Massachusetts.  From the parking are you will cross a beautiful bridge over the Housatonic River.  The trail crosses railroad tracks and immediately begins to climb into the woods.  You will reach a split in the trail, a left will take you...
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  • Stockbridge, Massachusetts

    Mary V. Flynn Trail

    1.29 mi / 138 ft gain
    Mary V. Flynn Trail is an out-and-back trail that takes you by a river located near Stockbridge, Massachusetts.
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  • Lee, Massachusetts

    Beartown Mountain to Laura's Tower

    4.05 mi / 981 ft gain
    Beartown Mountain to Laura's Tower is an out-and-back trail that provides a good opportunity to view wildlife located near South Lee, Massachusetts.
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  • Great Barrington, Massachusetts

    Housie Rail Trail

    8.56 mi / 233 ft gain
    Housie Rail Trail is an out-and-back trail where you may see beautiful wildflowers located near Housatonic, Massachusetts.
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