Best to look for clubs or go out with a group of fellow jeepers.. People wont post addresses or specific locations to trails .. Look around here for other mass threads people meet up all the time and go out
Location: PEOPLES REPUBLIC OF MASSACHUSETTS, Somerset
My club is having it's annual Toy Run/Trail Ride on Sunday 12/1 that is open to the public. Will be an all day event that has something for everyone from stock to Buggy. Space is limited to 60 Jeeps and I believe at this point there are about 9 spots left open. Link below.