SR 14 begins at an intersection with US 360 in St. Stephens Church. The roadway continues on the north side of the intersection as SR 721, the old route of SR 14 that continues northwest to near Bowling Green. SR 14 heads southeast as The Trail, a curvaceous highway with multiple right-angle turns that serves as the primary north-south highway of King and Queen County. The state highway passes through the hamlets of Bruington, Henleys Fork, Stevensville, Cumnor on its way to the county seat of King and Queen Court House, which contains the county offices and the county's only high school. SR 14 continues southeast through the small communities of Truhart, Little Plymouth, Shanghai, and Elsom to its junction with SR 33 in Shacklefords. SR 14 and SR 33 run concurrently along the four-lane divided highway named for the decorated U.S. Marine Chesty Puller east to Shacklefords Fork, where SR 14 heads southeast along Buena Vista Road. After passing through Cologne and Plain View, the state highway veers east and crosses the Poropotank River into Gloucester County. SR 14 continues east a short distance as Adner Road to Adner, where the state highway turns southeast onto US 17. SR 14 and US 17 follow the four-lane divided highway southeast to Gloucester Courthouse, where US 17 bypasses the county seat on its way to Yorktown. SR 14 and US 17 Business head east on Main Street, along which the highways pass through a roundabout surrounding the county courthouse. At the east end of Gloucester Courthouse, SR 14 turns north onto John Clayton Memorial Highway, a four-lane divided highway. The intersection where SR 14 diverges from US 17 Business is also the eastern terminus of SR 3. SR 14 and SR 3 head north then curve east to cross Burke Mill Stream into Mathews County. Just east of the stream at Fort Nonsense, SR 3 turns north onto Windsor Road to head for Middlesex County and the Northern Neck. SR 14 reduces to two lanes and heads through Foster before reaching a junction with SR 198 just south of Hudgins. The state highways run concurrently south to the village of Mathews, where SR 198 veers east as Buckley Hall Road toward Moon. SR 14 turns south to pass through the county seat as Main Street, then becomes John Clayton Memorial Highway again as it continues in the direction of New Point Comfort, the point of land on the north side of the entrance of the York River to the Chesapeake Bay. In the hamlet of Bavon, SR 600 continues east toward New Point Comfort Natural Area Preserve while SR 14 turns south toward Bayside. The state highway turns west, then north, to a cul-de-sac at Bayside Wharf on Davis Creek.
