On April 16, 1827, a team of three surveyors were commissioned to determine a routing for a new highway leading from Hopkinton, a town in northeastern St. Lawrence County, to Lake Champlain. The task took 26 days, after which it was determined that the highway would meet Lake Champlain at Fort Kent. An act authorizing the construction of the highway was passed by the New York State Legislature on April 18, 1829. A total of approximately $38,500 (equivalent to $905,833 in 2019) was devoted to the project by the state of New York through the same act.
The 75-mile (121 km) highway opened in 1833 as a toll road named the Port Kent and Hopkinton Turnpike. The turnpike had only one toll gate, located near the center of the route. Two years later, the turnpike commissioners petitioned to the state of New York, asking for permission to replace the single gate with two gates at opposite ends of the turnpike that would collect half of the toll amount. The commissioners believed that the change in the toll gate locations would result in higher revenue, allowing them to continue maintaining the highway. The change was approved; however, the toll road was dissolved anyway three years later on March 30, 1838. At that time, maintenance of the Port Kent–Hopkinton highway was transferred to the towns it ran through.
The state of New York assumed maintenance of most of the Ausable Chasm–Port Kent roadway at some point after 1920. In the 1930 renumbering of state highways in New York, the entirety of the highway from Ausable Chasm to the Port Kent ferry landing was designated as NY 373, despite the fact that the small portion of the route east of Lake Street in Port Kent was not maintained by the state at the time. On April 1, 1985, ownership and maintenance of NY 373 east of Lake Street was transferred from the town of Chesterfield to the state of New York as part of a highway maintenance swap between the state and Essex County
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