Maryland Route 290 is a state highway in the U.S. state of Maryland. The highway runs 17.20 miles (27.68 km) from MD 300 at Dudley Corners north to MD 299 near Sassafras. MD 290 roughly parallels U.S. Route 301, which it intersects twice, as it connects the communities of Crumpton in northern Queen Anne's County and Chesterville and Galena in eastern Kent County. The portion of the route in Queen Anne's County was constructed as MD 301 in the early to mid-1920s. In Kent County, a portion south of Galena was built in the late 1910s and extended south to the Chester River in the late 1920s. MD 290 assumed the course of MD 301 in 1940 to avoid a number conflict with US 301. The Galena–Sassafras section of the highway was built in the late 1940s. MD 290 was reconstructed in Queen Anne's County and from south of Galena to Sassafras in the mid- to late 1950s. The highway's interchanges with US 301 were built when the U.S. Highway's course was constructed in the mid-1950s.

Maryland Route 300 is a state highway in the U.S. state of Maryland. Known for most of its length as Sudlersville Road, the highway runs 13.55 miles (21.81 km) from MD 213 in Church Hill east through Sudlersville to the Delaware state line, where the highway continues as Delaware Route 300. MD 300 forms part of an east–west connection between U.S. Route 301 in northern Queen Anne's County and Dover, Delaware. MD 300 between Church Hill and Dudley Corners was one of the original state roads marked for improvement in 1909, but the county constructed the highway with state aid in the mid- to late-1910s from Church Hill to Sudlersville. The highway from Sudlersville to the state line was built in the late 1920s and early 1930s. MD 300 was widened over its entire length around 1950 and extended west to US 213's bypass of Church Hill around 1970. MD 300 was officially split in two when its superstreet intersection with US 301 was built in 2005.