Richard Kingsmill, a prominent member of the Virginia Company, received one of the first 300-acre land grants in the southwest corner of what later became a much larger plantation. The land passed through Kingsmill's daughter Elizabeth - who married Colonel William Tayloe - and then to Lewis Burwell II in 1693, who paid 1,200 acres for the parcel. In the mid-1730s, British Colonel Lewis Burwell III established a 1,400-acre plantation here and named it for the Kingsmill family. He served as colonial customs inspector for the upper James River. Burwell's Landing, his inspection station along the river, included a tavern, storehouse, warehouse, and ferry house. Quarterpath Road - which still runs through the area - extended between Burwell's Landing and Williamsburg. The Kingsmill manor house burned in 1843. By 1860, the plantation was owned by William Allen, then perhaps the wealthiest man in Virginia. He continued to operate it using enslaved labor and held it through the Civil War. Only the office and the kitchen survive - among the earliest brick dependencies still extant in Virginia.

The Civil War rolled through these lands in 1862. Major General George B. McClellan's Peninsula Campaign forces - 121,500 men, 44 artillery batteries, 1,150 wagons, more than 15,000 horses - moved cautiously up the Peninsula from Fort Monroe. An English observer called it "the stride of a giant." Confederate General John B. Magruder, a former thespian sometimes called "Prince" John, held the Warwick Line east of Williamsburg with a much smaller force. He used elaborate theatrical ruses to convince McClellan that he was facing larger armies than he was - marching the same troops back and forth behind the lines in what historian Stephen Sears later called "performances of the Prince John Players." McClellan slowed accordingly. By the time he was ready to attack Yorktown, the Confederates had quietly withdrawn under cover of darkness, leaving Quaker guns - logs painted black - to fool him.

The Williamsburg Line was the third Confederate defensive line on the Peninsula. Designed under Benjamin S. Ewell, president of the College of William and Mary, it consisted of fourteen redoubts anchored between College Creek on the south and Queen's Creek on the north. Fort Magruder - Redoubt Number 6 - was an elongated pentagon with walls fifteen feet high and nine feet thick, surrounded by a dry moat nine feet deep, mounting eight guns. Several of the redoubts stood just east of Quarterpath Road, which led to the Kingsmill landing. On May 5, 1862, the Battle of Williamsburg was fought in rain and mud, with much of the action at or near Fort Magruder. Confederate casualties, including the cavalry skirmishing on May 4, were 1,682. Union casualties were 2,283. Most historians rate it a Confederate strategic victory - the Williamsburg Line delayed the Federals just long enough for the main Confederate army to continue its withdrawal to Richmond. Portions of Fort Magruder's earthworks still survive on Penniman Road in James City County.

By the early twentieth century, the Kingsmill Plantation lands had fallen into disuse. The hilly, wooded ground was poor for agriculture. John D. Rockefeller Jr. and his wife Abby Aldrich Rockefeller had acquired vast tracts in the area in the 1920s and 1930s while building Colonial Williamsburg, working with the Reverend W.A.R. Goodwin and the College of William and Mary. They lived at Bassett Hall, southeast of the Historic District. Their son Winthrop Rockefeller served as chairman of the Colonial Williamsburg Foundation - and, simultaneously, as Governor of Arkansas - in the 1960s and 1970s. During that period, Winthrop learned that August Busch II of Anheuser-Busch was considering Virginia for a major investment. The two men negotiated. The deal that followed brought Anheuser-Busch a brewery, the Busch Gardens Williamsburg theme park, the Kingsmill Resort, the Kingsmill on the James planned community, and several large commercial parks. The old Kingsmill Plantation land was made available for purchase to make it work. The result generated thousands of jobs and millions of dollars in new tax revenue for the region.

The Kingsmill on the James planned community runs along the river, with its own marina, golf courses, and grocery store. Past residents have included two-time US Open champion Curtis Strange, former Reagan chief of staff Donald Regan, NFL coach Marv Levy - and John W. Hinckley Jr., who attempted to assassinate President Reagan in 1981 and lived in Kingsmill following his court-supervised release. The Kingsmill Resort hosted an LPGA Tour event for many years, most recently as the Pure Silk Championship through 2021. The brewery sits just inland. Busch Gardens occupies a wooded ravine to the west. Quarterland Commons Commercial Park covers the eastern flank. Together they form a single Anheuser-Busch-shaped landscape - changed hands several times since the InBev acquisition of A-B in 2008 - that runs roughly from Highway 199 down to the James, with Quarterpath Road still threading through it the way it did in 1750. The kitchen and office of the original Kingsmill Plantation stand in a quiet corner, brick walls flush with the soil they were laid in three centuries ago.