well, Pittsfield is in the Berkshires, which could definitely give you a nice place to stop for a day or 2 in the fall. But you would need to rent a car to get around the area. Its not a place to be stuck without transportation. Pittsfield itself isn't very nice. It would be a great area to be in for a night or 2 if you can get a car.

The rest of your stops really don't lend themselves to tourism. Although I think that Springfield chamber of commerce post from a few days ago might try to convince you otherwise.

Worcester is a slightly depressed old mill city, and it does have a few nice restaurants, and a decent art museum, it just doesn't seem worth it as opposed to Boston. Framingham is just a suburb. Nothing to see, and impossible to get around without a car.

Once you get to Boston, you might take the train to Portland Maine for a couple of days. You can also do a single day trip to Rockport or Salem by train.

Portland, Rockport and Salem are great suggestions. Once in Portland you can take a mailboat cruise around the harbor or visit one of the islands.
Late Sept is a little early for fall color but you might see some just starting.

If you wanted to switch trains in New York, you could visit one of my old favorites. Mystic CT. Mystic has a lot to offer for the tourists. Albany-Renseleer to NYP to MYS is about $70pp.
The early morning train from Albany gets you to NYP to catch the train to Mystic at a reasonable hour.

The Amtrak station in Springfield is a very short taxi ride (could be walked) to the Peter Pan bus terminal. Peter Pan is the regional bus system -- Springfield is their hub and you could take a bus to just about anywhere in central or western MA or Connecticut.

If you like restaurants I would recommend Northampton MA or Amherst MA. If you want woods and scenery and a small town consider Lee or Lenox MA. From Amherst, Lenox, Lee, you could catch the bus to Pittsfield where you could resume your train trip.

Sorry, I read the trip Boston to Albany backwards -- Pittsfield comes before Springfield when travelling east. But you get the idea.

None of those towns (except for maybe Pittsfield) are the cute type of New England towns you are envisioning. I would NOT stop at any of them.

Instead, while in Boston, you could take the Commuter Rail to a number of cute towns. Salem, Gloucester, Newburyport and Rockport MA are possibilities. There's also Providence RI which has a lot of charm. You could also take the C&J bus to Portsmouth NH.

C&J Trailways does make several trips daily between Boston and Portsmouth, NH. The buses are usually not crowded, either. And their terminal is a nice indoor one, too -- but unfortunately, they're located a couple miles outside the town center in a park-and-ride. You have to take a taxi or local bus to reach the town center.

Greyhound runs only one or two times at most between Portsmouth and Boston, can be notably more crowded, and their stop is just an outdoor curb waiting area. But they have one advantage -- their stop is located right in the town center.

Another town easily reached by commuter rail from Boston is Concord.

Thanks for the responses. Think we will go for some day trips from Boston, maybe an overnight or two. The suggestions sound great, very much appreciated.

One of my guests just mentioned to me: Amtrak has train service from Springfield to North Hampton (just a twenty minute ride). North Hampton would be great (www.northamptonma.gov)! It's not a coastal town but it is a funky and fun New England college town.