Deerfield, Massachusetts

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

  • Ashburnham, Massachusetts

    Summit Mount Watatic via the Wapack Trail

    5.0
    3 mi / 800 ft gain
    Entering Mount Watatic in your GPS will take you to Rindge State Road (119), continue about two minutes down the road past where the GPS tells you. on the Right hand side you will will see a sign for Mount Watatic Parking area or just enter in coordinates: 42.696796, -71.904521 You will begin the...
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  • Sandisfield, Massachusetts

    Buck River Swimming Hole

    4.0
    0.3 mi / 250 ft gain
    This swimming hole is 7-feet deep. At the top of the swimming hole is a 12-foot waterfall with slide down. Parking: The swimming hole is located between Sandisfield Town Office and the post office. There is one dirt pull-off space near the swimming hole. The easiest parking is at the Town Offic...
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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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  • 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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  • Great Barrington, Massachusetts

    Mt. Wilcox and Beartown Mountain Trail Loop

    5.0
    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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  • Temple, New Hampshire

    Hike the North & South Peaks of Pack Monadnock

    5.0
    8.3 mi / 2290 ft gain
    This route will take you to both peaks and on most of the trails in this section of the park! Take the Wapack Trail (1.4 miles, rocky, challenging) to the summit of South Pack (2290') and climb the fire tower for some incredible views! On a clear day, you can see the Boston skyline. Then continue...
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  • Temple, New Hampshire

    Hiking Pack Monadnock at Miller State Park

    4.0
    2.8 mi
    Miller State Park is the oldest State park in New Hampshire and offers the perfect spring, summer or fall hike. From the parking area, visitors can choose from one of three trails: The Marion Davis Trail (1.4 miles to peak), The Wapack Trail (1.4 miles to peak) or the Auto-road (~ 1.0 miles to pe...
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  • Bennington, Vermont

    The Mile-Around Woods

    5.0
    1.33 mi / 243 ft gain
    The Mile-Around Woods in Bennington, Vermont, offers a moderate hiking trail that spans approximately 1.33 miles. The trail is circular, providing a continuous path through the woods. The terrain is varied, with some flat sections and others that are slightly hilly, making it suitable for interme...
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  • Great Barrington, Massachusetts

    Hike Monument Mountain

    4.5
    2 mi / 720 ft gain
    At 1642 feet (with a total elevation gain of 720 feet), Squaw Peak is a great spot to see both Mt Greylock along the Vermont border, and the Catskills in New York. There are several trail options here to get to the summit, but no matter which combination you choose, you can keep your trip under ...
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  • Granby, Connecticut

    Enders Falls

    4.0
    0.5 mi / 118 ft gain
    Enders State Forest sprawls over approximately 2000 acres, and is found within the towns of Granby and Barkhamsted in Connecticut.  Enders has a good sized parking lot directly on Route 219.  From the junction of Route 219 and Route 20, visitors will proceed west on Route 219 for 1.2 miles and tu...
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  • Shaftsbury, Vermont

    Lake Shaftsbury Loop

    4.0
    1.39 mi / 160.98 ft gain
    Lake Shaftsbury State Park is a small park in Southern Vermont between Bennington and Manchester. It is well-loved by locals as swimming spot in the summer, especially for families with kids.  Less well known is the nature trail that meanders around the perimeter of the lake. While only a mile in...
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  • Cropseyville, New York

    Hike Dickinson Hill Fire Tower

    4.5
    3 mi / 200 ft gain
    Once you drive onto N. Long Pond Road you will follow it appproximately 1.5 miles to the end. From the parking you can take the short walk back on the road to the start of the trail. The trail is actually a rough Fire Tower Road. You will follow this for about 1.3 miles. Here you will see a se...
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  • Norfolk, Connecticut

    Campbell Falls

    4.0
    0.99 mi / 161 ft gain
    Campbell Falls, one of the most beautiful parks in CT. Don't let the size of the park fool you, that's what adds to the beauty. With it's strong pine and fresh flower scented woods you slowly forget that you're even in Connecticut. The trails aren't labeled the greatest but still can be made out....
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  • East Nassau, New York

    Kinderhook Creek

    5.0
    1.62 mi / 308 ft gain
    Kinderhook Creek is a loop trail that takes you by a river located near Stephentown, New York.
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  • Glen Road, Vermont

    Hike the Lye Brook Falls Trail

    4.0
    4.7 mi / 938 ft gain
    The Lye Brook Falls Trail is a 4.7 mile hike through scenic trails just outside of Manchester Center, Vermont. The trail is open year-round, but the best time to go is during spring blooms or to see the fall colors. This hike is family friendly and fun for all ages. Dogs are allowed on this trail...
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  • Simsbury, Connecticut

    Hike to the Heublein Tower on Talcott Mountain

    4.3
    2.54 mi / 404 ft gain
    The Heublien Tower Trail, located just inside the Talcott Mountain State Park entrance off of Route 185 in Simsbury CT, is a short 1.25 miles. While the hike isn't long, the first 1/3 of a mile is a steep incline that will get your heart pumping. The trail itself it very well kept, and although ...
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