While I have done limited amounts of hunting in NH, NY and VA, I hunt Mass. a lot, primarily for deer, and I find it relatively satisfactory for how I like to hunt. Many towns (at least in Eastern Mass.) have restrictions on hunting. State forests, on the other hand, pretty much all allow hunting. So do WMA's (see the DFWELE Website for a listing). WMAs are stocked with pheasants and some people have luck with grouse and wood cock hunting and of course waterfowl.

Unlike some other states, if private land is not posted, it is not illegal to hunt (assuming proper stand off distance etc.). Not that I would recommend doing that (at least for private ownership), but you would probably not get into trouble with your license if you happen to cross a boundary line. You can't use a rifle to hunt deer (shotgun, bow, ML only), you can to hunt coyote (during the day) and bear and I guess groundhogs and other varmints if that is your thing. Since you are so close to both CT and RI, each of those states have longer bowhunting seasons than does Mass. I even think RI runs through the end of January. Although it is too late this year, I understand that your part of the state has pretty good turkey hunting. Lastly, even though this is not the forum, don't forget to try striper fishing which is the sporting activity that we are best known for.

Good luck.