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The Best Backpacking in Massachusetts

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

Top backpacking spots in and near Massachusetts

  • Great Barrington, Massachusetts

    Camp at Beartown State Forest

    On a spontaneous adventure, we were lucky to have ended up car camping at the beautiful Beartown State Forest. From the main entrance of the state forest, the campsite is only a few minutes drive to the right of the road. The campsite is popular, but only limited to 12 sites, so during the summer...
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  • Ashburnham, Massachusetts

    Wapack Trail: Mount Watatic to Barrett Mountain

    17.49 mi / 2838 ft gain
    Wapack Trail: Mount Watatic to Barrett Mountain is an out-and-back trail that takes you through a nice forest located near Ashburnham, Massachusetts.
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  • Cheshire, Massachusetts

    The Cobbles via Appalachian Trail

    1.64 mi / 738 ft gain
    The Cobbles via Appalachian Trail is an out-and-back trail that takes you past scenic surroundings located near Cheshire, 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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  • Taunton, Massachusetts

    Massasoit Trails

    7.99 mi / 669 ft gain
    Massasoit Trails is a loop trail that takes you by the lake located near Middleborough, Massachusetts.
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  • Carver, Massachusetts

    Plymouth Wishbone Walking Trail

    14.06 mi / 922 ft gain
    Plymouth Wishbone Walking Trail is a point-to-point trail that takes you by a lake located near Plymouth, Massachusetts.
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  • Egremont, Massachusetts

    Appalachian Trail from Jug End to Bear Mountain

    10.81 mi / 3074 ft gain
    Appalachian Trail from Jug End to Bear Mountain is a point-to-point trail that takes you by a lake located near Great Barrington, Massachusetts.
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  • Mount Washington, Massachusetts

    Alander Mountain and Brace Mountain Loop

    11.07 mi / 1667 ft gain
    Alander Mountain and Brace Mountain Loop is a loop trail where you may see beautiful wildflowers located near Sheffield, Massachusetts.
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  • North Adams, Massachusetts

    Mount Prospect, Mount Williams, and Mount Greylock Loop via Appalachian Trail

    13.37 mi / 4652 ft gain
    Mount Prospect, Mount Williams, and Mount Greylock Loop via Appalachian Trail is a loop trail where you may see beautiful wildflowers located near North Adams, Massachusetts.
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  • Ashburnham, Massachusetts

    Wapack Trail

    20.95 mi / 3799 ft gain
    Wapack Trail is a point-to-point trail where you may see beautiful wildflowers located near New Ipswich, New Hampshire.
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  • Douglas, Massachusetts

    Ridge-Wallis-Mid State Trail

    12.55 mi / 1007 ft gain
    Ridge-Wallis-Mid State Trail is an out-and-back trail that takes you by a lake located near Douglas, Massachusetts.
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  • Ashburnham, Massachusetts

    Midstate Trail: Blackburn Village to Nutting Hill

    13.97 mi / 2195 ft gain
    Midstate Trail: Blackburn Village to Nutting Hill is an out-and-back trail that takes you by a lake located near Ashburnham, Massachusetts.
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  • Spencer, Massachusetts

    Midstate Trail: Browning Pond to Barre Falls

    11.35 mi / 1001 ft gain
    Midstate Trail: Browning Pond to Barre Falls is a point-to-point trail that takes you by a lake located near Worcester, Massachusetts.
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  • Great Barrington, Massachusetts

    East Mountain via Appalachian Trail

    9.25 mi / 1857 ft gain
    East Mountain via Appalachian Trail is an out-and-back trail where you may see beautiful wildflowers located near Great Barrington, Massachusetts.
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  • Great Barrington, Massachusetts

    Mt. Wilcox and Beartown Mountain Trail Loop

    9.29 mi / 981 ft gain
    Mt. Wilcox and Beartown Mountain Trail Loop is a loop trail that takes you by the lake located near Great Barrington, Massachusetts.
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  • Douglas, Massachusetts

    NS Trail Wallum Lake to Richardson Trail

    9.62 mi / 787 ft gain
    NS Trail Wallum Lake to Richardson Trail is a point-to-point trail that takes you by a lake located near Douglas, Massachusetts.
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