I'd also recommend the D2R2 which starts in Deerfield, MA and goes into Southern VT. There's several different routes with the longest being up to 180k. Very hilly but beautiful rural gravel roads. If you fly into Boston, it's not very far to drive to the Deerfield area so that could be very convenient for you. Even flying into New York wouldn't have a very long drive although Boston is definitely closer. It runs in August but they have the cue sheets on-line so you could ride on your own if you're so inclined (that's what I've done and pieced together variations of the different routes).