WIS 57 replaced WIS 78 in the Door Peninsula in 1930, reaching its present-day terminus in Sister Bay. This routing from Milwaukee to Sister Bay stayed mostly the same until the 1990s, with a few minor exceptions. WIS 57 was rerouted onto its current alignment between Hilbert and Askeaton in 1932, replacing a former routing to Hollandtown; the original routing was replaced by county roads. The highway was also realigned between Plymouth and Kiel in 1956, and the former route became part of WIS 67.