The southwestern corner of Connecticut, otherwise known as the Gold Coast, was once home to potato farmers and fishermen until 19th-century railroads brought New Yorkers north. With their blue-chip companies they transformed Fairfield County into one of the wealthiest regions in the USA, with the affluent town of Greenwich at its heart. Now financial firms, yacht clubs and gated communities line the shore. You must ply further north to New Canaan, Ridgefield and Redding for the original Colonial flavor of the area, although the perfectly clipped lawns and spotless clapboards are tell-tale signs that many New Yorkers also have second homes here.
Further north along the coast, Stamford, once a stage-coach stop on the New York-to-Boston post road, is the area’s commercial and industrial hub, while Norwalk and Westport have quietly thriving cultural communities with radically different characters.