Top Adventures in Great Barrington

  • Hike Monument Mountain

    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 com...

    2 miles 720 ft gain

  • 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, ...

  • Hike the Lookout Trail in Beartown State Forest

    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 o...

    0.5 miles 117 ft gain

  • Hike the Benedict Pond Loop Trail

    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 ...

    1.7 miles

  • Hike to Laura's Tower and Ice Glen

    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...

    2.58 miles 600 ft gain

  • Hike to Race Brook Falls

    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 H...

    3.4 miles 1174 ft gain

  • Hike Mount Everett

    Depending on when you do this hike, you may drive into Mount Everett State Reservation to find the gates open or closed to traffic.  The gates are generally open in the summer during the day (closed at night) so people can drive all the way up to ...

    4.6 miles

  • Hike Tyringham Cobble

    You can choose to start the loop in either direction.  I chose to start of and take a right.  You will pass through a section of wide open meadow full of goldenrod.  Then as you ascend you will enter the woodlands featuring many stone walls.  Even...

    2.1 miles 450 ft gain

  • Explore Bash Bish Falls

    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 an...

    1 miles

  • Swim in the Buck River

    his swimming hole is 7 feet deep. At the top of the swimming hole is a 12-foot waterfall with slide down. There is developed camping on the NY side in Copake Falls NY - Taconic State Park. You can also swim in a water-filled quarry: there is a rop...

    0.3 miles 250 ft gain

  • Climb Alander Mountain

    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 Bis...

    10.6 miles 2250 ft gain

  • Hike Mount Frissell to Brace Mountain

    This 5.2 mile round trip out/back hike takes you through three states. You start the hike on Mt Washington Road just across from the stone pillar designating the Connecticut/Massachusetts border. At 0.5 miles you reach Round Mountain 2289 feet. 1....

    5.2 miles 1000 ft gain

  • Nearby camping, hotels, and more

    • Hillsdale, New York

      Hillsdale Hideaway

      Perched above the historic hamlet of Hillsdale, NY, enjoy your own private mountaintop with panoramic views of the Harlem Valley. Surrounded on three sides by a state park and a thousand-acre Audub...

      From $115/night

    • New Marlborough, Massachusetts

      Echo Hill

      This quiet, secluded camp on over 30 acres is a great place to unplug and rewind. There is also plenty to do in the towns nearby!Echo Hill is located in the heart of the Berkshire Mountains, home t...

      From $150/night

    • Canaan, New York

      The Lodge's Campsite

      Picturesque camp in the middle of a forest. Enjoy the isolation and quiet at your tent, or experience all that the Berkshires and Taconics have to offer. Because you cannot drive to the tent, man...

      From $75/night

    • Richmond, Massachusetts

      Berkshire Mountain Hideaway

      Magical, quiet campsite, only a short walk ( less than 1/4 mile) ) from easy access parking. Glacial rock to one direction, seasonal spring stream to another. Hiking trails right from the site to P...

      From $120/night

    • Salisbury, Connecticut

      Glacial Erratic At Moore Brook

      Camp next to your own Glacial Erratic between Moore Brook with a refreshing swimming hole and a trail up the ridge, past the ski jumps, and on to the Appalachian Trail. In the opposite direction, a...

      From $150/night

    • Ancram, New York

      Malowina

      MALOWINA FOREST is a magical place of tranquility, wonder and breathtaking beauty where people deepen their love affair with nature and reconnect with their higher selves. Surrounded by the vibrant...

      From $125/night

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