Located in the Gold Coast along the Long Island Sound, it is 48 miles (77 km) northeast of New York City and is part of the Western Connecticut Planning Region.

[3] The earliest known inhabitants of the Westport area as identified through archaeological finds date back 7,500 years.

[4] Records from the first white settlers report the Pequot Indians living in the area which they called Machamux translated by the colonialists as beautiful land.

[5] Settlement by colonialists dates back to the five Bankside Farmers; whose families grew and prospered into a community that continued expanding.

[4][full citation needed] During the Revolutionary War, on April 25, 1777, a British force of 1,850 under the command of the Royal Governor of the Province of New York, Major General William Tryon, landed on Compo Beach to destroy the Continental Army's military supplies in Danbury.

[7] Minutemen from Westport and the surrounding areas crouched hiding while Tryon's troops passed and then launched an offensive from their rear.

[8] An additional statue of two cannons facing the water, a testament to the resistance the minutemen displayed, was erected on the beach in 1901.

[13] Blight caused the collapse of Westport's onion industry, leading to mills and factories replacing agriculture as the town's economic engine.

[4][14] During this period artists, musicians, and authors such as F. Scott Fitzgerald moved to Westport to be free from the commuting demands experienced by business people.

[15] The roots of Westport's reputation as an arts center can be traced back to this period during which it was known as a "creative heaven.

[16][17] From the 1950s through the 1970s, New Yorkers relocating from the city to the suburbs discovered Westport's culture of artists, musicians and authors.

[14] The population grew rapidly, assisted by the ease of commuting to New York City and back again to rolling hills and the "natural beauty of the town.

"[4][18] By this time Westport had "chic New York-type fashion shopping"[19][20] and a school system with a good reputation, both factors contributing to the growth.

[14][18][19][20][21][22] By the 21st century, Westport had developed into a center for finance and insurance, as well as professional, scientific and technical services.

Westport is bordered by Norwalk on the west, Weston to the north, Wilton to the northwest, Fairfield to the east and Long Island Sound to the south.

[35] In 2018, data from the American Community Survey revealed that Westport was the 9th wealthiest city in the United States.

Joe Biden outscored Donald J. Trump by more than 50 points in 2020, marking the best performance for a Democratic presidential nominee in the town in over 60 years.

[49] Westport was one of five towns in Connecticut that backed former Governor John Kasich over Donald J. Trump in the 2016 Republican presidential primary.

Westport's first newspaper dates back to the printing and publication of the first issue of The Saugatuck Journal on December 26, 1828.

[67] Among the many actors, singers and other entertainers who have lived in town is Paul Newman who resided in Westport from 1960 until his death in 2008.

[68][69] Fala (1940–1952), President Franklin D. Roosevelt's dog, was an early Christmas gift from Mrs. Augustus G. Kellogg, a town resident.

[70] Actress Grace Carney moved to Westport in 1979, when she became president of United Tool and Die, a company started by her father.

[74] Jean Donovan, a lay Roman Catholic missioner martyred in El Salvador in 1980 grew up in Westport and graduated from Staples High School.