Darien

The preppy coastal town of Darien is slightly less metropolitan than Greenwich and slightly less rural than Westport, making it just the right pick for its residents, who love its charm, small size, and delightful waterfront location. Darien residents sing the praises of Weed Beach and Pear Tree Point, its two public beaches, as well as the Ox Ridge Riding & Racquet Club, a well-known equestrian training facility. There are plenty of well-established traditions here, but Darien is changing, too. In late 2021, The Corbin District broke ground, a planned redevelopment of seven acres of Darien’s downtown into a mixed-use district that will eventually boast apartment buildings, office space, shopping, and restaurants. Relative to its neighbors, Darien has one of the easiest one-hour commutes to New York City: Commuters can either take Metro-North directly into Grand Central or drive in on I-95 or the Merritt Parkway.

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Living in Fairfield County

Fairfield County is often called Connecticut’s Gold Coast, referring to its string of waterfront towns that glisten in the sun, with hubs of finance interlaced with beach towns and nautical villages—albeit villages with some of the most prosperous populations in the country. The station names called off by the train conductors evoke images of ultimate suburbia: Greenwich, Stamford, Darien, Norwalk, and Westport. Residents have long been drawn to Fairfield County because of its proximity to New York City, thanks its many stops on the commuter rail. It also offers idyllic country acreage, much of it with views and access to the Long Island Sound. Houses here include aristocratic estates, where sailing and horseback riding is still a part of daily life; glass-walled Modernist icons; and solid, historic clapboard Colonials that might have been models for a 19th-century painting.