Hi Howie, I'm probably the other NEW YAWKER here.
Live just outside of Monticello and know exactly what you mean about finding places to ride.
My best suggestion is to do like I did and join a hunting club that has lots of land and allows members to ride.
Hunting season is only about three weeks of the year but we ride year round unless the snow gets too deep.
Getting caught where you're not allowed to be can get painfully expensive in this state and the cost to join a hunting club will be cheaper.
Welcome aboard!