Before the English arrived, much of the coastal plain draining to the Chesapeake Bay was called Tenakomakah in Algonquian - 'densely inhabited land.' The Powhatan Confederacy, built by a paramount chief named Wahunsunacock (1547-1618) and known to history as Powhatan, brought roughly thirty tribes under one political order. Powhatan's second capital, Werowocomoco, sat along the north bank of the York River in present-day Gloucester County across the water; archaeologists rediscovered the site in the early 21st century. The Chiskiack people, a Powhatan Confederacy tribe, lived along the York River inside what is now York County until the 1630s, when escalating conflict with the English forced them west. The English took the village's name for their own settlement nearby - Kiskiack - and that ground is now part of Naval Weapons Station Yorktown. Cheesecake Road and Cheesecake Cemetery inside the base preserve the English mangling of 'Chiskiack.' In 1570, Spanish Jesuits had briefly founded the Ajacan Mission here, guided by a Native American interpreter they called Don Luis who had been captured years earlier and educated in Mexico. In February 1571 Don Luis led an attack that killed all the Jesuits except a young boy. The Spanish did not try again.

English colonists arrived at Jamestown in 1607. In 1619 the Virginia Company of London organized the area into 'citties': what is now York County fell across Elizabeth Cittie and James Cittie. The eight original shires followed in 1634 - Charles River Shire one of them - and the shire was renamed York County in 1643, the same time the Charles River became the York River. Yorktown grew along the river as a port. In October 1781, after a brilliant joint Franco-American siege, British General Cornwallis surrendered at Yorktown, ending major fighting in the American Revolutionary War. The Moore House, where the surrender terms were negotiated, still stands. Yorktown is one of three points of the Historic Triangle - Jamestown and Colonial Williamsburg are the others - linked by the National Park Service's bucolic Colonial Parkway. Heritage tourism here is now a major economic engine.

Look at York County from the air and the U.S. military's footprint reads as physical geography. The Coast Guard Training Center Yorktown sits on the York River. Naval Weapons Station Yorktown, established by order of President Woodrow Wilson in 1918 to support World War I mine-laying operations, covers most of central York County and shares 14 miles of York River shoreline. Camp Peary, established in World War II as a Seabee training base, later housed sensitive German naval POWs whose capture had to be hidden from Berlin because their code books were thought lost at sea. Many of those former prisoners eventually settled in the United States after the war. The combined federal land divides the county into two population clusters: dense suburban development in the south, more recent growth in the north tied to Williamsburg. Building the bases erased communities, including the original Lackey (locally called 'the Reservation' and largely populated by Black landowners), Halstead's Point, Penniman, Bigler's Mill, and Magruder. Many displaced families and their descendants live in Yorktown, Gloucester, Lee Hall, Grove, and Lightfoot.

York County also wraps around the affiliated theme parks: Busch Gardens Williamsburg sits at the western edge, with the Water Country USA water park inside the county. A small industrial corridor on the York River east of Yorktown holds a Dominion Virginia Power plant and a petroleum terminal on the site of a refinery that closed in 2010. The county's median household income hit $84,167 in 2010 - the highest in Hampton Roads - and is now home to over 70,000 residents in places like Tabb, Grafton, Seaford, Dare, Lightfoot, and Yorktown itself. Politics here used to be reliably Republican; the county voted in landslides for Herbert Hoover in 1928 and stayed strongly Republican for decades. The trend has softened. Jimmy Carter took more than 45% of the vote in 1976. Joe Biden cleared 45% in 2020. In 2024, Kamala Harris won 46% in York County - the highest Democratic share since 1964. In 2025, Abigail Spanberger won a majority of York County's votes for governor, though Republicans carried it in the lieutenant gubernatorial and attorney general races down ballot. Three hundred ninety years after Charles River Shire, the politics here are still shifting.