There is nothing of any real challenge in eastern MA. Freetown is open but ONLY the roads that are posted as open to motor vehicles. Maps are available online for Freetown SF.
Your best bet is to simply join a club. Most are only $50 a year and thats about half what a simple trespass ticket will get you. Ignorance of the law won't get you out of a ticket.
Although there are some places in western MA that are legal open roads, and getting you there is easy.. getting one through the woods is near impossible. There are turns that end up on private land, one even ends up on the wrong side of a shooting range. Imagine trying to give directions through the woods.. "Take a left at the tree that looks like an old man carrying a sack..." just doesn't work.
I'd go to
EC4WDA -- East Coast 4 Wheel Drive Association -- NorthEast Region for more info on New England clubs.
A nice deal is that all of our clubs offer an open invite to fellow association members, so, you can't make your own club's monthly ride, just hook up with one of our sister clubs. Last year, between our 15 clubs, we offered over 120 events throughout the season.
Or email me if you have any other questions:
E4WBrill@aol.com
Talk soon,