The Best Hiking in Deerfield

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

Top hiking spots in and near Deerfield

  • Deerfield, Massachusetts

    Rock via Old Pine Nook Road

    1.32 mi / 259 ft gain
    Rock via Old Pine Nook Road is an out-and-back trail that provides a good opportunity to view wildlife located near Deerfield, Massachusetts.
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  • Montague, Massachusetts

    Canalside Rail Trail

    7.23 mi / 223 ft gain
    Canalside Rail Trail is an out-and-back trail that takes you by a river located near Deerfield, Massachusetts.
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  • Deerfield, Massachusetts

    North Sugarloaf via Brookside and Pocumtuck Ridge Trail

    2.93 mi / 594 ft gain
    North Sugarloaf via Brookside and Pocumtuck Ridge Trail is a loop trail where you may see beautiful wildflowers located near South Deerfield, Massachusetts.
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  • Greenfield, Massachusetts

    Temple Woods Loop Trail

    2.84 mi / 299 ft gain
    Temple Woods Loop Trail is a loop trail that takes you through a nice forest located near Greenfield, Massachusetts.
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  • Greenfield, Massachusetts

    Sachem Head

    1.82 mi / 59 ft gain
    Sachem Head is a loop trail that provides a good opportunity to view wildlife located near Greenfield, Massachusetts.
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  • Sunderland, Massachusetts

    Sunderland Caves and Sugar Shack via Robert Frost Trail

    2.42 mi / 446 ft gain
    Sunderland Caves and Sugar Shack via Robert Frost Trail is a loop trail where you may see beautiful wildflowers located near Sunderland, Massachusetts.
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  • Sunderland, Massachusetts

    Mount Toby via Sugar Farms to Summit to Tower Loop

    5.96 mi / 1037 ft gain
    Mount Toby via Sugar Farms to Summit to Tower Loop is a loop trail that takes you by a river located near Sunderland, Massachusetts.
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  • Sunderland, Massachusetts

    Mount Toby via Robert Frost Trail

    3.08 mi / 948 ft gain
    Mount Toby via Robert Frost Trail is an out-and-back trail where you may see beautiful wildflowers located near Sunderland, Massachusetts.
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  • Sunderland, Massachusetts

    Sugar Farms Trail to Tower Road Loop

    6.54 mi / 915 ft gain
    Sugar Farms Trail to Tower Road Loop is a loop trail that takes you by a waterfall located near Sunderland, Massachusetts.
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  • Sunderland, Massachusetts

    Mount Toby Trail

    4.25 mi / 856 ft gain
    Mount Toby Trail is a loop trail that takes you by a river located near Sunderland, Massachusetts.
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  • Deerfield, Massachusetts

    South Sugarloaf Trail

    1.48 mi / 404 ft gain
    South Sugarloaf Trail is a loop trail that takes you by a river located near South Deerfield, Massachusetts.
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  • Deerfield, Massachusetts

    South Sugarloaf Mountain

    0.68 mi / 331 ft gain
    South Sugarloaf Mountain is an out-and-back trail that takes you through a nice forest located near South Deerfield, Massachusetts.
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  • Deerfield, Massachusetts

    North and South Sugarloaf

    2.76 mi / 840 ft gain
    North and South Sugarloaf is a loop trail that provides a good opportunity to view wildlife located near South Deerfield, Massachusetts.
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  • Leverett, Massachusetts

    Mount Toby via Tower Road

    3.82 mi / 827 ft gain
    Mount Toby via Tower Road is an out-and-back trail that provides a good opportunity to view wildlife located near Leverett, Massachusetts.
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  • Millers Falls, Massachusetts

    Lynn's Falls Loop

    2.05 mi / 344 ft gain
    Lynn's Falls Loop is an out-and-back trail where you may see beautiful wildflowers located near Wendell, Massachusetts.
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  • Shelburne Falls, Massachusetts

    High Ledges via Dutch and Mary Barnard to Waterthrush Loop

    2.16 mi / 272 ft gain
    High Ledges via Dutch and Mary Barnard to Waterthrush Loop is a loop trail that provides a good opportunity to view wildlife located near Shelburne Falls, Massachusetts.
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