Discover a wealth of scenic hiking trails and incredible views of the southern Berkshires at majestic Monument Mountain in Great Barrington, Massachusetts. The trails, which are short, offer hikers a few loops. Indian Monument Trail is 1.5 miles long and encompasses 300 years of history. Hikers will encounter everything from ancient Native American trails, the stone walls of old sheep pastures, and cart paths to roads that horse-and-carriages traveled upon, foot paths, and roads that once were used by Model T’s made by Ford. Just under a mile long, Hickey Trail is the most direct route to the summit of Monument Mountain. Featuring the best views, Squaw Peak Trail is a little over one-half mile long and it connects the Indian Monument and Hickey Trails.
Those with the ability to reach Squaw Peak, which, at over 1,600 feet high, is the high point of Monument Mountain will be treated to some spectacular vistas. These include the Housatonic River Valley, Mount Greylock near the Vermont border, and New York’s Catskill Mountains. Bird watchers will be treated to hawks and, on occasion, bald eagles. Since there’s an elevation gain of 720 feet, hikers need to be in good shape. Remember to wear proper footwear and make sure to take along lots of water. When it rains or snows, the trails can be treacherous, especially along the ledges, so be cautious. Monument Mountain is open all year, from sunrise to sunset. It’s recommended that two hours are allotted for your visit.