Monument Mountain is a highly-visited hiking destination in Great Barrington. The trails are sprinkled with wooden bridges, small waterfalls, rock walls, a set of stairs made from stone, and small wildlife, that all come together to form a pretty adventurous atmosphere. Parking is available right at the foot of the mountain (don’t forget to visit the meter before you start walking). There are three trails to hike: Indian Monument, Hickey, and Squaw Peak. The peak looks out over the Housatonic River Valley and has plenty of gorgeous views. It’s important to note that these trails are not fully suitable for anyone that has under a basic level of fitness capabilities. The scattered ledges create really unique viewpoints, but can become very slippery during and after rainfall.

Squaw Peak makes hiking the trails even more worthwhile. There’s plenty of spots to gaze out  over the ocean of trees in the valley below. The huge boulders that at—and around—the peak are great for taking a moment to sit down and take everything in. Each perspective is unique and adrenaline rushes are almost guaranteed here. The numerous earthy ledges—although very enticing—have no fencing of any sort, so children and pets should be watched carefully. 

Great Barrington, at large, is full of unique places to visit. Just 7 minutes south of Monument Mountain is The Prairie Whale, a restaurant and bar with tons of delicious options on the menu. If the weather is nice, outdoor seating and activities are available there.