Trip Recommendations (Western MA)

Hi! I’m looking to see if there are any other cities that it would be worth doing a rail trip to from either Northampton, MA or Springfield, MA.

We are looking for a train time less than ~5 hrs long to an interesting and walkable city (one Uber to and from the station is fine) for this winter. All of the places that come top of mind, I think we have been to, so I’m curious if anyone has other recommendations.

We have been to: Boston, MA, Providence, RI, Brattleboro, VT, Burlington, VT, NYC, and Albany, NY.

Thank you!