Long before European settlement, the land that is now Annandale was inhabited by Indigenous peoples, predominantly the Doeg (or Tauxenent) tribe, who utilized the fertile Piedmont region and local waterways for hunting and agriculture. European colonists arrived in the late 17th and early 18th centuries, establishing large tobacco plantations and, later, mixed-use farms.
The community was officially named in 1830 when a local settler from Scotland named his plantation after the Scottish town of Annan, at the mouth of the River Annan. A post office was established that same year. In the 1850s, the construction of the Little River Turnpike—a toll road connecting Alexandria to Aldie—spurred economic growth and established Annandale as an essential waypoint for farmers transporting goods.
During the American Civil War, Annandale saw frequent troop movements and minor skirmishes due to its strategic location on the turnpike between Washington, D.C., and the Confederate strongholds of Northern Virginia. Following the war, the area returned to a quiet agricultural existence, notable primarily for dairy farming.
The most transformative era in Annandale's history occurred after World War II. As the federal government expanded, an influx of workers to the D.C. area triggered a massive suburban housing boom. Annandale rapidly transitioned from a rural farming community to a bustling suburb of mid-century brick ramblers and colonials. In the late 20th century, relaxed immigration laws brought a new wave of demographic changes. By the 1990s, Annandale had emerged as the epicenter of the Korean-American community in the Washington metropolitan area, profoundly shaping its modern cultural and economic identity.