Destination Westport: In Gatsby’s Shoes

September 15 - 29

Join Westport Historical Society on either September 15, or September 29, as Richard “Deej” Webb and Robert Steven Williams, recreate the summer of 1920 and the sites and characters that influenced Fitzgerald’s Great American novel. Come prepared for a gorgeous, vigorous 120 minute walk in one of the East Coast’s most beautiful settings. Please bring water and wear comfortable walking shoes. Reservations are recommended.

Imagine it’s the summer of 1920. Westport is a sleepy farm community that lures New York’s most glamorous couple-F. Scott and Zelda Fitzgerald—to its shores. Seeking respite from their whirlwind Jazz era lives, the Fitzgerald’s set up in an 18th century farmhouse that has seen Revolution and the building of a nation over many decades. Zelda swims daily in the peaceful waters of the Long Island Sound while Scott takes advantage of the bucolic quiet to work on what he hopes will be his next great novel—The Great Gatsby.

PARKING INFORMATION: Guests should park at Longshore Marina, along the asphalt and dirt areas. Parking passes will be distributed by tour guides the day of, to place on cars.


Longshore Marina
Westport, CT 06880
United States




(203) 222-1424

How to Get There