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Stockbridge, Massachusetts

Top Spots in and near Stockbridge

  • Savoy, Massachusetts

    Tannery Falls Loop

    0.54 mi / 135 ft gain
    The hike to Tannery Falls may be a little confusing, I'll clear it up for you before you even go there! To get to The falls you will travel down a dirt road that isn't very well maintained during the winter. As you keep driving down the dirt road you will notice a pond , which means you are almos...
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  • Sharon, Connecticut

    Hike the Pine Knob Loop, Housatonic Meadows SP

    5.0
    2.5 mi / 770 ft gain
    The Pine Knob loop is a 2.5 mile loop trail that takes you through beautiful thick  woods filled with vistas, wild flowers and tons of wild life.  You will start your adventure at the Pine Knob Trail head where you will be able to a Connecticut Appalachian trail guide. Pine Knob is a blue blaze ...
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  • Stanfordville, New York

    Explore Wethersfield Estate & Gardens

    The Wethersfield Estate is a beautiful estate and property located less than 2 hours north of New York City. The gardens are expansive and extremely beautiful, open to the public each day from noon to 5pm (COVID-19 hours). Additionally, there are trails for horseback rides, carriage rides, dog-wa...
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  • Granby, Connecticut

    Hiking Enders Falls

    4.0
    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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  • 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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  • Holyoke, Massachusetts

    Whiting Street Reservoir Loop

    3.74 mi / 138 ft gain
    Whiting Street Reservoir Loop is a loop trail that takes you by a lake located near Holyoke, Massachusetts.
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  • Kent, Connecticut

    Explore Kent Falls

    5.0
    0.75 mi / 250 ft gain
    Every now and then you need a day to rest those sore muscle from all your recent adventures. The only issue is, you don't want to sit around inside, you want to be outside. Insert a trip to Kent Fall State Park. The perfect rest adventure day.Located 1 hour and 45 minutes north of New York City i...
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  • Kent, Connecticut

    Hike the Ridge Loop Trail, Macedonia Brook SP

    3.0
    For a quick weekend trip from Newport, RI, Macedonia Brook State Park had a lot to offer for its size. In three or four hours, with lunch, you can hike the 6.4 mile ridge trail and get some fresh air without having to hike on too busy of trails. The elevation gain is only around 700 ft, however, ...
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  • Greene County, United States

    Hike to Newman's Ledge

    4 mi / 584 ft gain
    Located in the beautiful Catskill Mountains, this is an outdoors-mans(and woman's) dream spot! Although this hike is accessible year round, if you decide to go during the summer you should expect crowds. Luckily, there are so many different trails and activities that it won't even matter. North-S...
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  • Haines Falls, New York

    Summit North Mountain

    4.5
    6 mi / 855 ft gain
    Have you ever wanted to feel as if you were hiking two different locations at once? If so, then North Mountain is definitely somewhere to check out. Take the birch tree forests around Aspen, CO and pair it with the spruces/pines of the Adirondacks and you'll have this route in the Catskills.Parki...
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  • Haines Falls, New York

    Fawns Leap

    2.3
    Please be respectful if visiting this local swimming hole. Pack out what you pack in, carry out others' trash, and familiarize yourself with Leave No Trace principles.  Hidden in the Catskill Mountains is one of the coolest cliff jumping locations I have ever been to. The first time I went was a...
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  • Elka Park, New York

    Layman's Monument and Kaaterskill Falls

    3.05 mi / 892 ft gain
    Layman's Monument and Kaaterskill Falls is an out-and-back trail that takes you to one of New York's tallest waterfalls at 231 feet and to the historical monument for Frank D. Layman, who passed away in 1990 while fighting a forest fire. This trail is located near Haines Falls, New York.
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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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  • Haines Falls, New York

    Kaaterskill Falls

    4.5
    2.57 mi / 719 ft gain
    Although this is a super short hike, it is definitely a tough one! The quick, steep climb is totally worth it once you reach the 260 foot cascade and pool at the end. Hike along the trail, hugging Spruce Creek all the way to the falls. If you hike in the spring, the creek and the falls will be ra...
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  • Albany, New York

    Blueberry Hill East

    1.73 mi / 59 ft gain
    Blueberry Hill East is a loop trail where you may see beautiful wildflowers located near Albany, New York.
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  • Albany, New York

    Blueberry Hill West Red and Yellow Trail

    1.37 mi / 52 ft gain
    Blueberry Hill West Red and Yellow Trail is a loop trail where you may see beautiful wildflowers located near Albany, New York.
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