HISTORY

Westport’s unique character can be traced to the town’s roots in the Native American tribes who defined the area. The five original “Bankside Farmers” settled in modern-day Greens Farms in 1648. Caption: The “Bankside Farmers” who settled in the Greens Farms neighborhood in 1648.

During the Revolutionary War, battle broke out during the British raid on Danbury. Some 1,850 British soldiers landed on Compo Beach on April 25, 1777, and marched up Compo Road, burning homesteads and barns as they went. After a battle at Ridgefield, the British returned through the village of Saugatuck and fought the local militia in a battle at Compo Hill. The Minute Man statue commemorates this event.

Kemper’s Tannery, constructed in 1835, now the iconic Westport Country Playhouse, where Joanne Woodward was Artistic Director. Her husband Paul Newman part-owned the adjoining restaurant until his death in 2008. Around 1910, artists discovered Westport and the town was literally turned into a nationally known beehive of cultural activity; the Famous Artists School and the Famous Writers School were both built here, attracting talent from all over America.

A postcard of Fountain Square on The Post Road, then called State Street, at the Main Street intersection dominated by a fountain. Circa 1910.

Norman Rockwell painting at the Famous Artists School in 1955.

The Famous Writers School in 1961. Rod Serling, screenwriter and narrator of ‘The Twilight Zone’ pictured far right.

F. Scott Fitzgerald and his wife, Zelda, photographed outside their home on Compo Road South in 1920.

Novels, plays, and movies have been written, produced, and filmed in Westport. From F. Scott Fitzgerald’s time in town writing The Great Gatsby to the television hit, I Love Lucy, and The Twilight Zone. Ray Dalio founded Blackrock Financial, the largest hedge fund in the world here. With Westport as an idyllic backdrop, actors, actresses, writers, artists, architects, businessmen and political figures have all made this town their home.

Ray Dalio, Founder and Co-Chairman of Bridgewater Associates, who chose Westport as the place to build the largest hedge fund in the world.

Through the years, Westport has become one of the most affluent suburbs in America, culturally rich and dichromatic; filled with a blend of old Yankee farmers, academics, and professionals from all fields, reflecting its international flavor.

Map of Saugatuck Village from 1803.
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FAMOUS PAST RESIDENTS:
Paul Newman
Martha Stewart
Michael Bolton
Joanne Woodward
Marlo Thomas
Phil Donahue
ENTERTAINMENT FILMED IN WESTPORT:
Billions
American Housewife
The Sisterhood of the Traveling Pants 2
The Stepford Wives