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 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 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) . 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. Route description NY 404 begins at NY 590 exit 8 in Irondequoit as Empire Boulevard, although the portion of Empire Boulevard between NY 590 and the Rochester city line is also state maintained as NY 941B, an unsigned reference route. Irondequoit Bay is northeast of this intersection, and Empire Boulevard serves as the northernmost non-bridge route from one side of the bay to the other; that is, between the inner-ring suburbs of Irondequoit and Brighton and the outer-ring suburbs of Webster and Penfield. The four-lane Empire Boulevard heads east from NY 590, intersecting North Winton Road (former NY 47) in a residential neighborhood before descending into a valley surrounding the bay. NY 404 continues east across the base of the valley, crossing the southern tip of the bay at the Irondequoit–Penfield town line. At the eastern edge of the bay valley, the route begins to turn to the northeast, slowly ascending in elevation as it heads away from Irondequoit Bay. The terrain levels off at the top of the valley, where NY 404