VT 314 was originally designated as Vermont Route F-3 in the late 1920s. The roadway on the New York side was unnumbered until , when Cumberland Head Road was designated as NY 314. VT F-3 was redesignated as VT 314 in 1964 to match the designation present at the New York ferry approach. In 2005, a new highway connecting US 9 to the ferry landing by way of the interior of Cumberland Head was completed and opened to traffic as the Commodore Thomas MacDonough Highway. NY 314 was realigned to follow the new highway while ownership and maintenance of its old alignment was transferred to the town of Plattsburgh. The designation of NY 314 east of US 9 was removed by July 2014.