My starting point is Canaan, NY. All on the bike. I remember the shoulders were a bit narrow heading South from Pittsfield (and non-existent going through Pittsfield). So, heading NE would be better? Maybe I'll work out a route on Map My Ride and see what it means for hills. Be nice to see some new country although I like the charm of Stockbridge and Lee, etc. Road bike 18 speed.