 It is the southernmost spot on Maryland's western shore, the coastal region on the western side of the Chesapeake Bay.Captain John Smith, the famed explorer who surveyed the Mid-Atlantic region for the British Crown, came ashore at Point Lookout in 1608.He surveyed the lands and waters of the area, including the mouth of the Potomac River on the south side of Point Lookout and its small nearby tributary, the St. Mary's River.