MD 363 connects Princess Anne and U.S. Route 13 (US 13) with the communities of Deal Island, Chance, and Dames Quarter on Tangier Sound in northwestern Somerset County.

The state highway heads north as a two-lane undivided road, sharply curving before crossing Middle Creek.

The route passes a boat ramp accessed from Ralph Abbott Road before a high-level bridge carries it over Upper Thorofare, a strait between Laws Cove and Tangier Sound.

After passing Haines Point Road, which leads to a large public boat ramp, the state highway continues northeast across the two branches of Rock Creek and through more marshland before entering Dames Quarter.

After passing to the south of Venton, which features the historic home Panther's Den and All Saints Church, MD 363 traverses the Chesapeake Forest Lands.

The roadway continues east through the Princess Anne Historic District toward MD 675 (Somerset Avenue) in the center of the town.