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  • Great Barrington, Massachusetts

    Top Spots in and near Great Barrington

    • 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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    • 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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    • 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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    • Sheffield, Massachusetts

      Race Brook Falls

      4.0
      2.47 mi / 1145 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

      Bash Bish Falls

      4.3
      0.75 mi / 295 ft gain
      Bash Bish Falls is a spectacular 60-foot waterfall located on the Massachusetts-New York border in the southern Berkshires. This popular destination offers easy hiking access and stunning natural beauty, making it perfect for families and casual hikers. Parking Options Massachusetts Side: 0...
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    • Copake, New York

      Bash Bish Falls from Taconic State Park

      1.53 mi / 167 ft gain
      Bash Bish Falls from Taconic State Park is an out-and-back trail that takes you by a waterfall located near Copake, New York. Swimming is not permitted at Bash Bish Falls. 
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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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    • 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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    • 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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    • 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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    • 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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    • 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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    • 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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    • 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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    • 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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