Bailey's Crossroads draws its name from the Bailey family of circus fame, which has long been connected with the community. Hachaliah Bailey (the founder of one of America's earliest circuses, which in time evolved into the Bailey component of what became the Ringling Bros. and Barnum & Bailey Circus) moved to Northern Virginia in 1837, bought the land surrounding the intersection of Leesburg Pike and Columbia Pike in Fairfax County, Virginia near Falls Church, Virginia, and gave Bailey's Crossroads his name. The Crossroads then became the winter quarters for his circus.
The opening months of the American Civil War proved to be a disruptive and unforgettable episode in the history of Bailey's Crossroads. From the summer of 1861, when the area fell into an uncomfortable and poorly defined "no man's land" between the borders of two warring countries, until late November of that year, when the area hosted a massive troop review, anything akin to normalcy was in short supply.
After the Civil War Bailey's Crossroads returned to its pastoral pre-war pursuits. The area remained a rural farming community until the post-World War II years, when a massive wave of development occurred. Leesburg Pike is now a commercial corridor, with apartments and homes to its north and south.
During the 1960s, as Washington's Metro system was being conceived, original plans called for a subway line to extend under Columbia Pike to and through Bailey's Crossroads. As a result of the plan a massive highrise complex was built on the former Washington-Virginia Airport in the heart of Bailey's Crossroads called Skyline City. Its location coincided with the planned locations of Metro stations. Plans for the Metro, however, changed. The western line was placed along the I-66 corridor instead.