The following is extracted from “A Walking Tour Guide to Westport, NY”:

 

From the early 1600’s, Lake Champlain played an important role in some of the most well-known chapters of American history.  And Westport’s own history, which begins in 1764, has been shaped both by the dramatic events of war and by the ongoing and steady development of transportation, industry and the commercial uses of natural resources.  As we consider the history of Westport, it becomes apparent that the special beauty and richness of her land and water resources have been the foundation for the cultural and historic traditions of village life.

In 1764, Westport’s history begins when William Gilliland, a successful colonial merchant, surveyed an area in the southern part of the town.  He was subsequently granted 2300 acres which he named Bessboro after  his daughter, Elizabeth.  One of Gilliland’s colonists, Edward Raymond, built the first recorded dwelling in the year 1770 on that part of Bessboro which is now close to Camp Dudley.  Raymond’s pre-Revolutionary War endeavors also included the construction of a sawmill and a gristmill.  By 1777, the Revolutionary War reached Bessboro.  Naval warfare was witnessed off her shores as Benedict Arnold retreated from his fight at Valcour Island pursued by the British.  He burned his boats directly across the lake in what is now Arnold’s Bay and retreated on foot to Crown Point, New York.  During this time, Raymond’s mills supplied boards and ash for Arnold’s boats and huts.  Raymond is believed to have been able to operate his mills as long as he did because of his relatively close proximity to the effort at Crown Point.  However, the small settlement lay in the path of Amherst Burgoyne’s march from Canada to Saratoga, and in the wake of Burgoyne’s defeat, the settlement was completely destroyed.  The first permanent settlement at Bessboro took place in 1785 when Major Hezekiah Barber settled at Barber’s point which is south of the village.  His family has owned and farmed the property for over 200 years, and indeed, agriculture has always existed as a major component of the area’s economy.

As we consider the history of the Westport village area, we need to back-track to 1771 when Philip Skene was granted 2400 acres north of Bessboro up to the middle of the present-day village.  This property came into the hands of a group of developers, including Platts and Rogers, their friends and relatives.  One of these men, John Halstead, had Ananais Rogers survey part of his lot and subdivide this area into separate properties running from the north of Washington Street to the south side of Liberty Street.  This first survey, undertaken in 1800, was done while Halstead was building Westport’s first village structure: a house and tavern on the southeast corner of Washington and Main Streets [across the street from the present-day Inn on the Library Lawn]. 

Another early settler, Judge Charles Hatch, came to Westport from Essex in 1804.  When he arrived he found a sawmill, one frame house, three log houses and a barn occupying the location of today’s village center.  Judge Hatch proceeded to build a store and began dealing in iron ore, rich deposits of which were found in the Westport area.  The next survey, which Hatch had Diodorus Holcomb undertake for him in 1819, covered the tract of land from the center of the village and extending to the north.  During this time, war again threatened Westport when, in 1812, the British came as close as two miles away in an attempt to destroy Macdonough’s fleet at Otter Creek.

After 1812, the reality of war became more remote to Westport life and the town grew quickly and confidently as transportation developed and natural resources were utilized.  By 1850, Westport had a population of 2,350 people.  Many of the forests had been cut to produce lumber, charcoal and potash.  The fields that remained yielded large quantities of agricultural products such as grain, potatoes, vegetables and fruit, as well as providing grazing land for cattle and sheep.  Iron was also important to the economy and there were many small mines located primarily along the Bouquet and Black Rivers.  Larger furnaces were built around 1850.  These included the Sisco Furnace just north of the village, the Norway Furnace near the Yacht Club dock, and the Payne Forge at Wadhams.  Although these furnaces produced substantial amounts of pig-iron for several years, by 1885 they had all gone out of business.

Transportation was vital to the development of Westport, with Lake Champlain providing a navigable route for the shipment of commodities and passengers.  By 1790, ferries were running from Rock Harbor to Basin Harbor and from Barber’s Point to Arnold’s Bay.  Steamboats came early to the lake when, in 1808, the world’s second steam-powered vessel was launched on Lake Champlain.  Barges, schooners and other vessels followed quickly and facilitated the shipment of natural resources and products to and from the village.  By 1823, the Hudson Canal was completed, connecting Westport to Albany and New York City.  But once the Delaware and Hudson Railroad came through town in 1876, water travel was to some extent superseded.  The railroad allowed many people fro the city easy access to the scenic beauty of the area and tourism increased dramatically.  By 1916, paved roads further increased accessibility and Route 9N, which runs through Westport, was a main artery.  The Adirondack summer visitor began to arrive in the 1880’s and Westport welcomed visitors with a variety of inns and boarding houses.  As in the past, Westport continues to be enjoyed by both resident and visitor alike.

Originally, Westport was a part of the town of Crown Point.  In 1798 it became part of Elizabethtown, including what was then called Northwest Bay.  Westport became a separate town in 1815 and the Village of Westport was incorporated in 1907