MD 289 serves Quaker Neck, a peninsula between Langford Creek and the Chester River southwest of Chestertown in Kent County.

MD 289 begins at a wye between Lands End Road and Cliffs City Road near Cliffs City, which lies near the southwestern end of Quaker Neck between the Chester River to the south and east and the East Fork Branch of Langford Creek to the north and west.

MD 289 passes west of Philip G. Wilmer Park and the Chestertown Armory before the highway makes an S-curve, within which its name changes to Cross Street and it passes east of the southern terminus of the Gilchrest Rail Trail and the Chestertown Railroad Station.

[1][2] MD 289 was constructed as a concrete road beginning in 1923, when the highway was completed to Wilkins Lane.

The highway was widened to 20 feet (6.1 m) and resurfaced with bituminous concrete from Wilkins Lane to High Street in Chestertown in 1953.