As Mr. Legs mentioned, we did a multi-day tour last year from Boston to Gardner, MA, then Gardner to Newfane, VT (passing through NH and crossing the CT River to Brattleboro), then Newfane back east to Petersham, MA (and that day had the biggest climbs of the trip). Last day was a shorter ride to Worcester, MA, to take the commuter rail back to Boston. It was a great trip!