From the parking area on the west side of US-7, two trails lead to the summit. Off Indian Monument Trail, look for a cairn about 100yds off the trail that marks the grave of the Indian maiden for whom Squaw Peak is named. Turn right and continue, always selecting the right spur. The second, more difficult trail (ascent 45min) begins to the right of the parking area and is blazed with round white markers. From the rocky summit, called Squaw Peak after an Indian maiden who leaped to her death from this point, you will behold a sweeping view of the Berkshires.