northern berkshire here,(williamstown). we wheel and ride atvs all over within probably 20 mins max of my home. there is tons of trails with all different difficulties. some you have a VERY hard time making in a built jeep, some you could ride on a scooter. if you are ever in the area just ask someone with a lilfted rig, they can point you in the direction.
If you are ever down on Cape Cod, there is a local spot in Mashpee that we call the "back roads", tons of dirt roads, Sand pits, trails through the woods, right next to Otis Air Force base, my friends and I all go wheelin there, quads and dirtbikes too, A great spot and in the summer time we have 100+ pallet bonfires.