Westport is a town of 27 000 people in Connecticut on Long Island Sound, part of Connecticut’s affluent “Gold Coast”. Only 50 km or so from New York City, it is the ninth richest city in the US. It would be about an hour’s drive from Stars Hollow.
It is a favourite location in fictional works – it was the home of Samantha and Darrin Stephens on Bewitched, and Lucy and Ricky Ricardo move here to start a new life in I Love Lucy. It also features in the film The Man in the Gray Flannel Suit.
The Annotated Gilmore Girls 