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.
And the town still belongs to its minutemen. H. Daniel Webster, a young sculptor who settled in Westport in 1906, modeled his militiaman on First Selectman Lewis P. Wakeman; Tiffany & Co. cast the bronze, and on June 17, 1910 — Bunker Hill Day, chosen deliberately — over a thousand people came by road, train, and trolley for a clambake, a parade, and the unveiling above the beach the town had secured for the public in 1902. A pair of government cannons, placed at Compo in 1901, already guarded the shore. Webster's statue is one of only four known minuteman monuments in the country, it appears on the town flag, and Westporters still dress him for the seasons — a Santa cap in December, rabbit ears at Easter.
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.
