Route: Monadnock - Wachusett (NH, MA)

Monadnock to Wachusett ties together two of the most popular hiking destinations in the Boston area. In addition to the two main summits, you summit a smaller peak, Gap Mountain, and traverse a series of trails (Pumpelly, White Arrow, Royce, Midstate, and Old Indian), fire roads, and bike paths (Monadnock Recreation Rail Trail, North Central Bike Path, and Heywood Branch Bike Path) as you go from one mountain to the other.  The route is about 75% off road, goes through the towns of Jaffrey, Fitzwilliam, Winchedon, Gardner, Westminster, and Princeton.