Westport’s Compo Beach was the site of the British invasion of Danbury, also known as Tryon’s Raid.
Near Compo Beach is the famous Minuteman Statue, which faces away from the beach to commemorate the way the Minutemen hid until they could attack the large British army from behind.
The town was made famous by the I Love Lucy television show—it’s where Ricky and Lucy Ricardo (played by Desi Arnaz and Lucille Ball) moved after purchasing their new home.
Westport was also the fictional residence of Darrin and Samantha Stephens on the television series Bewitched.
The Twilight Zone episode “A Stop at Willoughby” featured a man who worked in New York City and commuted by train to his home in Westport. The episode was written by Westport resident Rod Serling and was aired on May 6, 1960.
The film The Girl Next Door was vaguely based on Westport. Director Luke Greenfield grew up in Westport. It was filmed and set in California.
One of the most popular tracks on REO Speedwagon’s debut album, released on Epic Records in 1971, was “157 Riverside Avenue.” The title refers to the Westport address at which the band stayed during the recording process.
In the musical Rent, Benny is married to Alison Grey of Westport, Connecticut, who comes from a wealthy family.
In the television series The West Wing, Bradley Whitford plays Josh Lyman, the White House Deputy Chief of Staff, who comes from Westport.
The movie The Man in the Gray Flannel Suit, based on the book by Sloan Wilson, takes place partly in Westport, and parts of the movie were filmed in Westport—the Westport Saugatuck train station in particular. The movie starred Gregory Peck.
In the late 1950s, the construction of a Nike missile base in Westport became the inspiration for the comedic film Rally ‘Round the Flag, Boys! The launch site has since been demolished and the radar site is now the location of the Rolnick Observatory, a public astronomical facility.