This hike is very popular, and for good reason. The Hickey Trail leads to the summit at a moderately steep grade. The Squaw Peak Trail then traverses the ridge, where there are great views of the Berkshires. Descend via the Indian Monument Trail, which is longer and more gradual than the Hickey Trail. My only criticisms are that despite its popularity, there are no restrooms at the bottom, and there are some large cliffs at the top.