The area known as Willoughby takes its name from Thomas Willoughby, who came to Virginia in 1610 as a boy of nine and received a land grant from England's King James I in what is now Ocean View around 1625. Willoughby's son, Thomas II, was living there in the 1660s, and legend has it that his wife awoke one morning following a terrific storm (possibly the "Harry Cane" of 1667) to see a point of land in front her home, where there had been only water the night before. The Willoughbys, it is said, were quick to apply for an addendum to the original land grant, giving them ownership of the "new" property.

Severe storms and hurricanes would continue to transform the contour of the coast, and the Willoughby holdings, for more than a century. During the fury of a hurricane on 19 October 1749, the ghost of a sand shoal was formed at Willoughby Point, and subsequent storms gave the shoal substance and shape until it grew into a sizable spit known as Willoughby's Sand Point or Sandy Point (now Willoughby Spit). A letter written from Annapolis MD after the 1749 hurricane reported that the "Chesapeake Bay rose 15 feet perpendicular. The tide kept fluxing ... and has carried small craft nearly a mile ... and left some in corn fields."

Willoughby Spit commemorates its 250th year of existence in October 1999.