The portion of NY 444 south of Main Street in Bloomfield was originally designated as part of legislative Route 14 by the New York State Legislature in 1908.

It heads north as a two-lane highway into the eastern portion of the village of Bloomfield, where it becomes known as Maple Avenue.

At the former "Four Corners" of Holcomb—its intersection with Main Street—NY 444 changes names to Elm Street, a moniker it retains until it exits the village.

[3] Back in the town of East Bloomfield, NY 444 becomes Victor–Bloomfield Road and follows a gently curving alignment through a rural, hilly portion of Ontario County.

[9] That same year, NY 20C was truncated to consist only of the portion of the route between the former "Four Corners" of Holcomb—the intersection of Main Street and Maple Avenue—and US 20.

[12] On September 1, 1996, the state of New York assumed ownership and maintenance of Elm Street in Bloomfield and CR 3, the continuation of Elm Street north of the Bloomfield village line to the Victor village line, as part of a county-wide highway maintenance swap.