High Quality Content by WIKIPEDIA articles! Maryland Route 404 is a major highway on Maryland`s Eastern Shore in the United States. It runs 24.61 miles (39.61 km) from Maryland Route 662 in Wye Mills on the border of Queen Anne`s and Talbot Counties, southeast to the Delaware state line in Caroline County, where the road continues as Delaware Route 404 to Nassau (near Rehoboth Beach). The Maryland and Delaware state highways together cross the width of the Delmarva Peninsula and serve to connect the cities west of the Chesapeake Bay by way of the Chesapeake Bay Bridge and U.S. Route 50 with the Delaware beaches. Along the way, MD 404 passes through mostly farmland and woodland as well as the towns of Queen Anne, Hillsboro, and Denton. The road is a two-lane undivided highway for most of its length with the exception of the bypass around Denton, which is a four-lane divided highway.