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.
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.
Why People Visit Westport Connecticut
- Spend a day at Compo Beach, the town's Sound-front park, and find the Minute Man statue on the bluff above the 1777 landing site — the 1901 commemorative cannons stand nearby.
- Walk the Saugatuck River waterfront and the historic Saugatuck village, the colonial shipping center the town grew from, and cross the 1884 Cribari swing bridge.
- Catch a show at the Westport Country Playhouse, founded in 1931 in a converted 1835 tannery, or a summer concert at the Levitt Pavilion.
- Browse downtown Main Street and the river walk, with shops and galleries near the water.
- Kayak to Cockenoe Island off Compo, or walk Longshore's shoreline paths and public golf course.
- Drive a stretch of the Merritt Parkway for its celebrated 1930s bridges — no two are alike.
- Read up at the Westport Library before exploring the town's deep arts-colony history.
