Pittsfield, Massachusetts

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

Top Hiking Spots in and near Pittsfield

  • 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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  • Salisbury, Connecticut

    Bear Mountain Loop

    4.7
    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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  • 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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  • Woodford, Vermont

    Woodford State Park Loop

    5.0
    2.41 mi / 203 ft gain
    A great loop for the summer, Woodford is also amazing when winter winter comes to the State Park. It also comes earlier than just about anywhere else in Southern Vermont. At 2,400 feet above sea level, this is an easy spot to find winter without spending a fortune at the local ski resorts. Woodfo...
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  • Wilmington, Vermont

    Ward’s Cove at Harriman Reservoir

    Harriman Reservoir — also known as Whitingham Lake — is one of Vermont's largest bodies of water, stretching over 2,000 acres through the hills of Wilmington and Whitingham in the southern Green Mountains. Ward's Cove is one of the reservoir's quieter access points, offering a sheltered launch ...
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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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  • 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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  • 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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  • 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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  • 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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  • 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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  • Niskayuna, New York

    Lisha Kill Preserve Loop

    4.5
    2.22 mi / 200 ft gain
    This 2.2 mile loop trail is lightly trafficked and great for all skill levels. Starting out the trail register, you will see signs from The Nature Conservancy which manages the preserve. Descending down a hill with lots of exposed tree roots, you will then cross over the meandering Lisha Kill and...
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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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  • Voorheesville, New York

    Hike the Keleher Preserve Loop

    2.0
    3 mi / 1636 ft gain
    The historic preserve is operated by the Mohawk Hudson Land Conservancy, so trails are clearly marked and extremely well maintained. There are features of the original farm that the land was used for from the 18th Century, including hand-thrown stone walls and an old logging road that cuts throug...
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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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