Keep in mind that finding legal wheeling spots in MA are hard to come by so in most cases you have to drive a bit. Your best bet is to find a handful of clubs that interest you and then see about getting in on a run or two. After you've hand the chance to wheel with them you'll be able to make the call on wether or not that club is right for you. You never know you could join a club based out of the Cape or one from the western part of the state. I think what you will find is that clubs have members from everywhere. Using us for example: Western Mass 4x4 started out as a thread on JeepForum that grew into a club, we have members all over the state from New Bedford to Lee, Lunenburg (NH line) to Uxbridge (CT line).
What are your rig specs?
What do you like to wheel?