Greenfield, New Hampshire

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

Top Hiking Spots in and near Greenfield

  • Erving, Massachusetts

    Rattlesnake Loop to Red Trail

    1.97 mi / 676 ft gain
    Rattlesnake Loop to Red Trail is a loop trail that provides a good opportunity to view wildlife located near Erving, Massachusetts.
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  • Andover, Massachusetts

    Haggetts Rail Trail to Haggetts Pond

    5.0
    2.08 mi / 16 ft gain
    Haggetts Rail Trail to Haggetts Pond is an out-and-back trail that takes you through a nice forest located near Lawrence, Massachusetts.
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  • Acton, Massachusetts

    Hike the Pratt's Brook Conservation Area Loop

    4.0
    1.5 mi / 85 ft gain
    Park in the small parking area right before the trailhead. *Notice this parking area is small and only fits about 3-4 cars so prepare to find street parking on a busy day. You can punch in the coordinates to a GPS if you need help finding it: 42.4545482, -71.4358192.  The loop is very diverse wit...
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  • 368 Weathersfield Trail, Vermont

    Hike Mount Ascutney

    3.0
    5.2 mi / 2326 ft gain
    This route to the top of Mount Ascutney is completed via the Weathersfield Trail. This trail goes past gorgeous Cascade Falls - often frozen in the winter months. There is a great spot to eat lunch at the top of Mount Ascutney to the side of the hang glider landing. While the summit itself does n...
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  • Concord, Massachusetts

    Walden Pond Path

    4.7
    1.65 mi / 49 ft gain
    Step into literary history and natural tranquility with a walk around the Walden Pond Path, located in Walden Pond State Reservation near Concord, Massachusetts. This iconic loop trail circles the pond made famous by Henry David Thoreau, who lived on its shores and wrote the American classic Wa...
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  • Marlborough, Massachusetts

    Hemingway Street Trail

    1.73 mi / 197 ft gain
    Hemingway Street Trail is an out-and-back trail that provides a good opportunity to view wildlife located near Marlborough, Massachusetts.
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  • Jamaica, Vermont

    Hamilton Falls

    3.5
    6.51 mi / 1431.32 ft gain
    The hike to Hamilton Falls is an enjoyable 6.8 miles roundtrip voyage through gorgeous forest scenery alongside a babbling brook. Be sure to visit the upper and lower falls! This trail is kid and dog friendly, so why not bring both?! If you are visiting the falls in the summer, bring a towel and ...
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  • Orange, New Hampshire

    Hike Cardigan Mountain via the West Ridge Trail

    4.8
    3 mi / 1200 ft gain
    Cardigan Mountain is located in Cardigan Mountain State forest just outside of Canaan, New Hampshire.  Just make sure to go to The Cardigan Mountain state park parking lot, via Cardigan Mountain Road and not the AMC Cardigan Lodge. The trail begins right from the parking lot where there is a port...
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  • Wilmington, Vermont

    Mount Olga Fire Tower Loop

    2.25 mi / 667.32 ft gain
    Tucked along Route 9 in Wilmington, Vermont, Molly Stark State Park is home to one of the most satisfying short hikes in the southern Green Mountains: the climb to the Mount Olga fire tower. At just 1.8 miles as a loop, it punches well above its weight — rewarding hikers with a genuine fire tow...
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  • Alexandria, New Hampshire

    High Cabin

    5.0
    4 mi / 1275 ft gain
    High Cabin, located in Cardigan State Forest, is owned and operated by the Appalachian Mountian Club (AMC). It was originally built in 1931 and since renovated in 2004. Renovations included a new roof, siding, bunk beds, a wood stove, and a composting toilet. It comes supplied with wood, bunks(st...
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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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