Westport is the birthplace of the Adirondack chair.
The town was founded by William Gilliland in 1764 who surveyed an area in the southern part of the town and was granted ; he also established the neighboring towns of Elizabethtown, named for his wife, and Willsboro. Gilliland originally called his patent "Bessboro" after his little daughter </Royce, Caroline Halstead (1902). Bessboro: a history of Westport, Essex Co., N.Y.. Open Library. p. 3.>. The original settlement, which may have supplied wood to Benedict Arnold's troops, was completely destroyed during the American Revolutionary War in connection with British General John Burgoyne's march from Canada to Saratoga. The first permanent settlement was in 1785.
The Town of Westport was established in 1815 from part of the Town of Elizabethtown. The community of Westport set itself off from the town in 1907 by incorporation. The Village of Westport abandoned this status as an incorporated village as of Dec 31, 1992.
By the mid-nineteenth century, Westport was a fashionable resort town. Its social scene was regularly reported on in The New York Times and by the Boston press. Like many other East Coast resorts, Its popularity gradually declined, starting in the 1930s, as first automobiles and then airplanes made possible a wider selection of vacation sites. Since the 1950s, however, Westport's lakeshore property has steadily increased in value. Although once most of the "summer people" stayed for weeks, now distinctions are not as clear: there are "year-round summer people" whose livelihood stems from outside Westport, weekenders whose principal residence is fairly close by (for example, Albany, which is two hours distant by car), and commuters to workplaces as distant as Plattsburgh, New York, and Middlebury, Vermont.
Westport is home to Camp Dudley YMCA, the oldest summer camp in continuous operation in the United States, founded in 1885 by Sumner F. Dudley, moved to Westport in 1891. Meadowmount, the summer school for string players founded by Ivan Galamian, is about eight miles (13 km) from the center of town. Westport is known as the ice fishing capital of Essex County.
Westport is also home to the only professional theatre in the Adirondacks proper. The Depot Theatre was founded in 1979, and operates out of the historic Amtrak railway station. The 136-seat, air-conditioned theatre hosts plays and musicals on its main stage during the Summer months, as well as an annual Gala. Outside of the Main Stage season, the Depot Theatre holds play readings, fundraisers, and receptions in the Depot Theatre Gallery located in the lobby.