NY 366 parallels Fall Creek from Varna to Freeville and passes along the southern edge of the Cornell University campus.

NY 366 enters the neighborhood of North Belle Sherman, bending northward as Dryden Road after the intersection with Maple Avenue.

Heading northeast out of the city, the route intersects with CR 122 (Caldwell Road) at the eastern edge of the campus.

NY 366 parallels Fall Creek through Dryden, sticking as a two-lane local road before entering the town of Freeville.

This intersection serves as the eastern terminus for NY 366, but the right-of-way continues out of Freeville as CR 105 (Fall Creek Road) toward the hamlet of Red Mills.

Unlike Route 9 before it, NY 13 bypassed Freeville to the south in favor of a direct alignment between Etna and Dryden.

[6][7] Also assigned at this time was NY 26, a highway that initially extended from Ithaca to Syracuse via Moravia and Skaneateles.

[11][12] In the early 1960s, a new expressway was built along the eastern shore of Cayuga Lake, bypassing downtown Ithaca to the west and north.