That's the type of riding I would love to be able to do, but here in southern Maine you would need a street legal bike and still have to dodge a lot of posted land. I have been looking for a late '70's to early '80's 2 stroke on/off bike for that exact purpose, but affordable ones in decent shape are impossible to find. An '81 Suzuki TS250 just went for almost $2000 a few towns away from me!! I would love to ride to work in the morning, and hit a couple trails on the way home, and then on the weekend, disappear all day.....
