I live in WMass, and work in CT. Gillette Ridge is great. My wife works at MetLife which is right on the course, so when she needs rides to work for whatever reason (car in shop, ect...) I try to get there 5 hours early!!
I was just at Wintonbury in Bloomfield. Great course also.
I am a member at Hampden Country Club, try that one out. Hampden is on the CT line, bordering Somers and Stafford, CT. 40 minutes from Hartford.
I also play a few rounds per year with a friend of mine from NH. We meet halfway, which , for us, happens to be right at Bernardston, MA and Crumpin Fox. The Fox has been voted best course in MA, so if you haven't played there, i'd give it a try. 30 minutes north of Springfield, MA.
other good courses are the Ranch in Southwick, MA, and the Ledges in South Hadley, MA. Both 20 minutes from Springfield.
Anybody wanting to play Hampden, let me know. I'm always up for a round.