Obviously Northampton, where I'd be able to see my grandfather every day and go to Jonathan Edwards' church whenever I felt like it.
I didn't know you had family in Western Mass! Do you ever visit the area?
My grandfather was a professor at UMass for some 50 years and lived in the same Amherst house through it all, until a couple years ago when he moved into a smaller place in Northampton with his partner. I've visited him many many times over years of family vacations; to the point where I'd say Amherst (and to some extent Northampton) is the city I know the best outside my own hometown. One of my favorite things we do in Western Mass when I'm there is driving through the Berkshires, where we often go to see Shakespeare & Company in Lenox.