Known as Piney Point Road, the state highway runs 9.84 miles (15.84 km) from St. George Island north to MD 5 in Callaway.

Just north of its terminus, MD 249 is a two-lane undivided road and begins to closely parallel a riprap along the Potomac River side of the island.

[1][2] Now on the mainland, MD 249 continues through the community of Piney Point, where the highway passes the entrance to the Paul Hall Center for Maritime Training and Education and Lighthouse Road.

The NuStar Energy property had previously been owned by Steuart Petroleum, which had taken over the land from the U.S. Navy, which operated the Piney Point Torpedo Testing Station during World War II.

MD 249 passes between the head of St. George's Creek and Tall Timbers Cove, then curves to the north through the community of Valley Lee.