New York State Route 404

New York State Route 404 (NY 404) is an east–west state highway located in eastern Monroe County, New York, in the United States. It extends for just over 10 miles (16 km) from an interchange with NY 590 in Irondequoit to an intersection with NY 104 on the Monroe–Wayne County line in the town of Webster. The route traverses the southern tip of Irondequoit Bay and passes through the village of Webster, where NY 404 intersects NY 250. Most of NY 404 passes through commercial areas; however, the western and eastern extents of the highway serve areas more residential in nature. The westernmost 3 miles (5 km) of the route is part of the Seaway Trail, a National Scenic Byway.

NY 404 largely follows the path of the Theodore Roosevelt International Highway, an early 20th century auto trail, through the towns of Irondequoit, Penfield, and Webster. Most of modern NY 404 was designated as NY 3 in 1924 and redesignated as U.S. Route 104 (US 104) c. 1935. In the early 1970s, US 104 was realigned to follow a new freeway between Irondequoit and Five Mile Line Road in Webster while NY 404 was assigned to US 104's former surface routing along the southern and eastern extents of Irondequoit Bay. NY 404 was gradually extended eastward to the Wayne County line over the course of the next decade as more sections of the freeway opened to traffic.