NY 301 was assigned as part of the 1930 renumbering of state highways in New York to the portion of its modern alignment west of US 9. At the same time, the section of what is now NY 301 from County Route 21 (CR 21) in Kent Cliffs to NY 52 in Carmel was designated as part of NY 130, which continued southwest from Kent Cliffs to Peekskill via CR 21, Oregon Road, and Division Street. By 1932, NY 301 was extended eastward to NY 130 in Kent Cliffs by way of its modern alignment. NY 130 was replaced by an extended NY 301 from Kent Cliffs to Carmel and eliminated entirely .