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Sheffield, Massachusetts

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

Top Hiking Spots in and near Sheffield

  • Sheffield, Massachusetts

    Hike to Race Brook Falls

    4.0
    3.4 mi / 1174 ft gain
    Hiking along the Appalachian trail I made a detour in Mt Everett State reservation. About a 2.5 mile detour lead me down to a beautiful 100ft waterfall called Race Brook falls. The waterfall felt made me feel like i was in the tropical jungle in Hawaii. Adding to the beauty of the waterfall were ...
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  • Mount Washington, Massachusetts

    Guilder Pond and Mount Washington Lookout Trail

    3.92 mi / 909 ft gain
    Guilder Pond and Mount Washington Lookout Trail is a loop trail that takes you by the lake located near Copake Falls, New York.
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  • Mount Washington, Massachusetts

    Climb Alander Mountain

    10.6 mi / 2250 ft gain
    Close to the popular Bash Bish Falls in Mount Washington State Forest is this amazing summit and perfect day hike! Witness the corners of Massachusetts, Connecticut, and New York all at once (and from the top of this trail, it connects to Bash Bish if you have the time to spear!) From the Mt. Was...
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  • Salisbury, Connecticut

    Bear Mountain Loop

    4.5
    6.05 mi / 1516 ft gain
    At 2,316 feet, Bear Mountain is the highest peak in Connecticut. The peak is about a half-mile south of the Massachusetts state line on the Appalachian Trail. The views are great. On a clear day you can see some of the peaks in southern New Hampshire. The remnants of a stone tower are on the summ...
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  • Mount Washington, Massachusetts

    Explore Bash Bish Falls

    4.3
    1 mi
    One of my favorite walks to a spectacular falls. The trail is easy to follow and one mile from NY parking lot and 0.5 from the parking lot. The apparent place to swim. There are several very nice, family safe swimmable pools in the creek above and after the falls. There are signs at the top of t...
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  • Mount Washington, Massachusetts

    Mount Frissell and Brace Mountain Loop Trail

    5.08 mi / 807 ft gain
    Mount Frissell and Brace Mountain Loop Trail is a loop trail where you may see beautiful wildflowers located near South Egremont, Massachusetts.
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  • Great Barrington, Massachusetts

    Hike the Benedict Pond Loop Trail

    5.0
    1.7 mi
    This is no ordinary loop, it's rain forest-like feels with small hills and curves, wooden bridges over marsh, and lookouts over the pond will keep you in awe at every corner! The trail is easy to find and easy to follow. When you park at the boat launch area, follow the blue blazes and trail sign...
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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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  • 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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  • Great Barrington, Massachusetts

    Hike the Lookout Trail in Beartown State Forest

    0.5 mi / 117 ft gain
    If you ever decide to go to the beautiful Beartown State Forest, be sure to enjoy the short but worthy hike to the vista on the Lookout Trail for views that stretches out to the mountains. There are two places to park:  1. From the main entrance of the park, you can get a spot at the lot at Bened...
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  • Norfolk, Connecticut

    Hike to Campbell Falls

    4.0
    1.4 mi / 187 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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  • Salisbury, Connecticut

    Explore Riga Falls

    The best part of the adventure is finding this hidden gem also known as Riga Falls. Riga Falls is actually one of Connecticut's lesser known waterfalls, but arguably the most scenic. A helpful hint is that the waterfall lies beside dirt road, keep your ears open! I've already said too much, happy...
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  • Great Barrington, Massachusetts

    Hike Monument Mountain

    4.0
    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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  • Canaan, Connecticut

    Explore Great Falls

    3.0
    0.5 mi
    Stumbled upon Great Falls in the Falls Village section of Canaan, CT. The stunning 50ft waterfall doesn't disappoint. very easy hike from parking lot, you must cross the river in order to get close for bottom view. Hop on top of turtle rock and relax as the waterfall tumbles in the distance.
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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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  • Hudson, New York

    High Falls Conservation Area Loop

    1.41 mi / 194 ft gain
    High Falls Conservation Area Loop is a loop trail that takes you by a waterfall located near Philmont, New York.
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