Greetings touring intelligence committee.
I have a new plan for the week-end: New Haven (CT) to Amherst (western MA) on Friday, and Amherst to Boston on Saturday.
If you have any tips for any leg of the journey on what best route to follow (or anything about the journey whatsoever - nice spots or good food), I would appreciate it very much.
You have the Rubel Maps? www.bikemaps.com. If not, you should grab some when you get into Massachussetts as they are a dream for cycling here. Also, don't forget about the commuter trains as a way to bail out or oddly reconfigure your trip into Boston. www.mbta.com. For example, it might be a nicer second day to go from Amherst up to Fitchburg and then take the train in to the city.
I've only been down to CT once for bike touring, but I really enjoyed Route 169 and the NE corner of the state, which maybe worth considering at some point.
That's a VERY ambitious two-day schedule you've got, there! Each leg is over 100 miles, so you've got a LOT of riding to do. But hey, since you asked, Amherst is a very nice town, with plenty of restaurants and little shops and green spaces. You also wouldn't have to go far out of town to find a quiet little camping spot either, I don't think.
Getting to Fitchburg on your bike and then taking the train could make your second day easier - Fitchburg is a mere 50 or so miles from Amherst, which should be a snap after getting to Amherst from New Haven!