Bailey's Crossroads is a census-designated place (CDP) in Fairfax County, Virginia, United States. The population was 24,749 at the 2020 census. Bailey's Crossroads lies at the crossroads of State Route 7 and State Route 244.

Virginia State Route 7 (VA 7) is a major primary state highway and busy commuter route in northern Virginia, United States. It travels southeast from downtown Winchester to SR 400 in downtown Alexandria. Its route largely parallels those of the Washington & Old Dominion Trail and the Potomac River. Between its western terminus and Interstate 395 (I-395), SR 7 is part of the National Highway System. In 1968, the Virginia State Highway Commission designated the road as the "Harry Flood Byrd Highway" between Alexandria and Winchester to commemorate Harry F. Byrd Sr. (1887–1966).