Spend An afternoon climbing a peak, discovering a waterfall, or both.

With a belly full of pizza and a pack full of locally grown or prepared food, hunger won’t be a problem as you hike Monument Mountain. Mountain and river views await you after a 720 foot climb in elevation to the peak. The entrance to Monument Mountain is about 4 miles from the center of town. Never underestimate the joy of reaching the top of a mountain and looking at the vast land below. Plan on at least two hours up and back.

Photo Credit: Andy Arthur

Walking through the woods on a quest to discover a waterfall is one of our favorite pastimes and as it so happens, arguably the best waterfall in the state, Bash Bish Falls, is only 30 minutes from downtown Great Barrington. While the hike to the falls is not long (15 minutes downhill, but remember, that means it’s an uphill climb out), it can get slippery. And don’t get any ideas, swimming is prohibited at the falls. But those who are game will get to enjoy the serenity of an 80 foot, twin drop waterfall that’s the highest waterfall in the state of Massachusetts.