Maryland Route 16 (MD 16) is a state highway in the U.S. state of Maryland. The state highway runs 51.06 miles (82.17 km) from Taylors Island east to the Delaware state line in Hickman, where the highway continues as Delaware Route 16 (DE 16). MD 16 connects Cambridge with several communities in northern Dorchester County and southwestern Caroline County, including East New Market and Preston. The state highway runs concurrently with U.S. Route 50 (US 50) near Cambridge, MD 331 between East New Market and Preston, and both MD 404 and MD 313 near Andersontown. MD 16 was constructed between Church Creek and Preston as one of the original state roads in the early and mid-1910s. The highway was extended in both directions in the late 1910s: north to what was to be designated MD 313 near Denton and west to Taylors Island. MD 16 was extended through Andersontown to the Delaware state line in the early 1930s. MD 16's bypass of Cambridge was constructed in the mid-1960s.

Delaware Route 16 (DE 16) is an east-west state highway in Delaware, mainly across northern Sussex County, with a small portion near the Maryland border in extreme southwestern Kent County. It runs from Maryland Route 16 (MD 16) at the Maryland border in Hickman east to the Delaware Bay at Broadkill Beach. The route passes through rural areas along with the towns of Greenwood, Ellendale, and Milton. DE 16 intersects DE 36 and U.S. Route 13 (US 13) in Greenwood, US 113 in Ellendale, DE 30 and DE 5 in the Milton area, and DE 1 between Milton and Broadkill Beach. West of DE 1, the route serves as part of a connection between the Baltimore–Washington Metropolitan Area and the Delaware Beaches. DE 16 was built as a state highway during the 1920s and 1930s. By 1936, the route was designated onto its current alignment.