Fairfield County 001 Bridgeport 1666 original county From the hundreds of acres of salt marsh that bordered the coast. 916,829 626 sq mi (1,621 km2) State map highlighting Fairfield County Hartford County 003 Hartford 1666 original county After the county of Hertfordshire in the UK 894,014 736 sq mi (1,906 km2) State map highlighting Hartford County Litchfield County 005 Litchfield 1751 From parts of Fairfield, Hartford and New Haven Counties City of Lichfield in the UK 189,927 920 sq mi (2,383 km2) State map highlighting Litchfield County Middlesex County 007 Middletown 1785 From parts of Hartford and New London Counties Former county of Middlesex in the UK 165,676 369 sq mi (956 km2) State map highlighting Middlesex County New Haven County 009 New Haven 1666 original county After New Haven Colony, founded as a haven in which Puritans could be free from persecution. 862,477 606 sq mi (1,570 km2) State map highlighting New Haven County New London County 011 New London 1666 original county After London, UK 274,055 666 sq mi (1,725 km2) State map highlighting New London County Tolland County 013 Rockville 1785 From parts of Hartford and Windham Counties Hamlet of Tolland, Somerset, UK 152,691 410 sq mi (1,062 km2) State map highlighting Tolland County Windham County 015 Willimantic and Putnam 1726 From parts of Hartford and New London Counties After Windham (now Wineham) in Sussex, England 118,428 513 sq mi (1,329 km2) State map highlighting Windham County