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Throughout the war, a constant battle was being fought across Long Island Sound as men from British-controlled Long Island raided the coast in whaleboats and privateers.Gold Selleck Silliman, whose home still stands on Jennings Road, was put in charge of the coastal defenses.As of the 2010 census, the town had a population of 59,404.

The trolley and later the automobile made the countryside accessible to these newly rich members of the middle class, who brought with them new habits, new attitudes, and new modes of dress. By the time of the Wall Street Crash of 1929, the population had increased to 17,000 from the 6,000 it had been just before the war.

Even during the Depression, the town kept expanding.

The Massachusetts General Court granted them permission to settle in the towns of Windsor, Wethersfield, and Hartford which is an area now known as Connecticut.

On January 14, 1639, a set of legal and administrative regulations called the Fundamental Orders was adopted, and established Connecticut as a self-ruling entity.

World War I brought Fairfield out of its agrarian past by triggering an unprecedented economic boom in Bridgeport, which was the center of a large munitions industry at the time.