History
By 1920, what would originally become DE 404 was an unimproved county road, with the section east of Bridgeville under contract as a state highway. The entire route of what would become DE 404 was completed as a state highway to a point northwest of Bridgeville by 1924. By 1931, the road was built as a state highway northwest to the Maryland border. When Delaware designated its state highways by 1936, DE 404 was designated to run from the Maryland border, where it connected to MD 404, southeast to DE 18 southeast of Bridgeville. The route followed its current alignment to Bridgeville, where it passed through the town on Market Street and South Main Street before picking up its current alignment east of US 13. At this time, what is now DE 404 past its then-eastern terminus was designated as part of DE 18. By 1987, DE 404 was extended east to DE 1 in Five Points, following DE 18 to Georgetown and US 9 (which had replaced a portion of DE 18) from Georgetown to Five Points. By 1990, DE 404 Alt. was created to bypass Bridgeville to the north and east, following Newton Road and US 13. DE 404 Alt. became a part of DE 404 by 1999, with the former DE 404 through Bridgeville becoming DE 404 Bus.
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