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.

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.

NY 404 continues east across the base of the valley, crossing the southern tip of the bay at the Irondequoit–Penfield town line.

The terrain levels off at the top of the valley, where NY 404 enters a major commercial strip that follows the route for 2 miles (3.2 km) into the adjacent town of Webster.

Route 30 exited Rochester on Empire Boulevard and followed it northeastward around Irondequoit Bay to where it merged with Ridge Road west of Webster.

[11] The designation remained in place until c. 1935 when NY 3 was supplanted east of Rochester by US 104, a new highway assigned to the length of Ridge Road between Lewiston and Oswego.

[14][15] The current super two highway paralleling Ridge Road between the Wayne County line and Sodus was built in the mid-1940s.

[16][17] US 104 was realigned in the late 1950s to follow a new section of the Sea Breeze Expressway between Ridge Road and Empire Boulevard.