Around 1910 something unexpected happened: artists. Illustrators, writers, and playwrights discovered the farmhouses and the shore light, and Westport became one of America's great arts colonies — F. Scott Fitzgerald rented a house on Compo Road South around 1920, and the Sound-shore world he found here is bound up with the one he later put into The Great Gatsby. In 1931 the players converted an 1835 tannery into the Westport Country Playhouse, still the town's stage today, and by mid-century the arts colony had settled into an affluent New York commuter town that never quite stopped being a colony.
Three old roads stitch the town together. The Boston Post Road — the colonial mail road, now US Route 1 — crosses the Saugatuck downtown, and mid-century travelers knew Westport by a roadside landmark on it: the Clam Box, a seafood stop whose sign and silhouette were pure New England. The Merritt Parkway sweeps through the backcountry under its famous 1930s bridges, no two alike, and the New Haven Line still carries commuters from the Westport and Saugatuck stations — the same ride to the city that turned onion fields into an arts colony and an arts colony into a suburb.
Why People Visit Westport Connecticut
Westport draws people who love the shore, the arts, and a good story. It is a Revolutionary-War landing site with a Minute Man on the beach, a colonial shipping village turned arts colony, and a Long Island Sound shoreline of beaches, river, and marsh. Visitors come for the rare mix — history you can stand on at Compo, theater and music in the summer, and a refined New England coast an easy train ride from New York.
