Boston: Mount Wachusett
Credit: John Phelan / Wikipedia

At 2,006 feet, Mount Wachusett – famous among locals for its small ski area, which incessantly broadcasts radio advertisements – is hardly an awe inspiring peak. But the views from the top are astonishing, especially on a clear day when Mt. Monadnock in southern New Hampshire rears into view. The Wachusett Mountain State Reservation is a well-maintained park, so expect dense forest, healthy meadows, and 17 miles of smooth trails. A visitor center sits at the top and makes a good spot for a picnic.