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Seaside Rowayton is a tiny peninsula village is surrounded by water, with the Five Mile River running along its western edge, the Long Island Sound to the south and east, and Farm Creek snaking through its center. Though technically part of Norwalk, Rowayton is generally considered its own entity. Here, everyone knows everyone, and with just a smidge over 4,000 people in town, it’s easy to see why. In some ways, Rowayton feels like a holiday seaside village, with kids riding their bikes to the town ice cream store or jumping off the swim platforms at Bayley Beach. But gaze across the water at the Manhattan skyline, and you’ll realize that Rowayton is the best of both worlds: It’s both a commuter and a beach town. Rowayton commuters love sipping their coffee on the riverside deck of Rowayton Market—open since 1753—before heading to the train, about an hour ride to Grand Central.

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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.