Pine Plains State Forest North-South Technical Loop

The Pine Plains loop strings together forgotten Depression-era logging roads that cut through 3,200 acres of Columbia County’s roughest terrain. You’ll hit the first real test at Roeliff Jansen Kill crossing — knee-deep water over bowling ball rocks that’ll humble cocky drivers fast. The north loop climbs through mixed hardwood forest on roads the CCC carved in the 1930s, with switchbacks that get tighter as you gain elevation toward the fire tower ruins.

This is solid intermediate territory requiring true 4WD with skid plates and good ground clearance. Creek crossings demand careful line selection, and the rocky climbs will test your diff locks. Best tackled May through October when water levels drop and mud firms up. No permits needed, but respect the hunting seasons. Pack recovery gear and extra water — cell service dies once you drop into the hollows, and the nearest gas is 15 miles back in Hillsdale.