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The Best Hiking in Lee

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

Top hiking spots in and near Lee

  • 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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  • 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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  • 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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  • Lee, Massachusetts

    Upper Goose Pond via Appalachian Trail

    6.56 mi / 922 ft gain
    Upper Goose Pond via Appalachian Trail is an out-and-back trail that takes you by a lake located near Lee, Massachusetts.
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  • Lee, Massachusetts

    Appalachian Trail: Pittsfield Road to Goose Pond

    10 mi / 1581 ft gain
    Appalachian Trail: Pittsfield Road to Goose Pond is a point-to-point trail that takes you through a nice forest located near Lee, Massachusetts.
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  • Great Barrington, Massachusetts

    Turkey and Airplane Trail

    3.22 mi / 302 ft gain
    Turkey and Airplane Trail is an out-and-back trail where you may see beautiful wildflowers located near Great Barrington, Massachusetts.
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  • Becket, Massachusetts

    Basin Pond Trail

    2.17 mi / 292 ft gain
    Basin Pond Trail is an out-and-back trail that takes you through a nice forest located near Lee, Massachusetts.
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  • Lee, Massachusetts

    Finerty Pond via Appalachian Trail

    5.97 mi / 1253 ft gain
    Finerty Pond via Appalachian Trail is an out-and-back trail that takes you by a lake located near Lee, Massachusetts.
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  • Lee, Massachusetts

    Appalachian Trail: Lee to Tyringham

    8.68 mi / 1437 ft gain
    Appalachian Trail: Lee to Tyringham is a point-to-point trail that takes you by a lake located near Becket, Massachusetts.
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  • Lee, Massachusetts

    Upper Goose Pond

    3.56 mi / 715 ft gain
    Upper Goose Pond is an out-and-back trail where you may see beautiful wildflowers located near Becket, Massachusetts.
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  • Lee, Massachusetts

    Hike Tyringham Cobble

    5.0
    2.1 mi / 450 ft gain
    You can choose to start the loop in either direction.  I chose to start of and take a right.  You will pass through a section of wide open meadow full of goldenrod.  Then as you ascend you will enter the woodlands featuring many stone walls.  Eventually the trail meets up with the Appalachian tra...
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  • Tyringham, Massachusetts

    Baldy Mountain

    3.03 mi / 1020 ft gain
    Baldy Mountain is an out-and-back trail that provides a good opportunity to view wildlife located near Tyringham, 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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  • 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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  • 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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