I've lived in Newport News for more than 20 years and don't know of any "legal" wheeling areas closer than a couple hours away. Best bet would be to link up with one of the local Jeep (or offroad) clubs as we do organized runs to places like Shoe Creek, GWNF, Crozet...etc.
If you're interested, swing on by the Dunkin Donuts in Newport News at the corner of Jefferson Ave and Denbigh Blvd at 10am on Saturdays. Our club (Middle Penn Jeep Assoc MPJAI) does a "Coffee Run" at that time.. basically hanging out shooting the breeze.
If you're interested.. from Glouseter just cross the bridge, turn right at Denbigh, drive 2 miles to Jeff and you'll see the Dunkin Donuts in the parking lot at the little shopping mall.
Although I'm pimping our club, there are several others in the vicinity.. all have good people in them. You can hit the Virginia Four Wheel Drive Association website and it has a listing of all the clubs in VA..