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 (Leesburg Pike) and State Route 244 (Columbia Pike).

Bailey’s Crossroads draws its state from the Bailey intimates of circus fame, which has long been connected with the community. Hachaliah Bailey, one of America’s first circus showmen, resided here. In 1808, while nevertheless in New York state, he purchased an Indian elephant which was one of the first such animals to attain the United States. Seeking a place to winter his circus animals, he moved to Virginia, and upon December 19, 1837, he bought a tract of land on the outskirts of Falls Church including what is now the intersection of Leesburg Pike and Columbia Pike. On this tract he built a large home known as “Bailey’s Mansion” or “Moray;” it was reputed to have contained 100 rooms. The mansion sat at a location now known as Durbin Place. It abutted Glenforest Drive, the oldest outlet road to Leesburg Pike.

Circuses were portion of the Bailey relatives business. Hachaliah’s son Lewis Bailey (1795–1870) operated a travelling circus and pioneered the use of canvas circus tents in the past eventually settling in 1840 to farm land in Bailey’s Crossroads. Hachaliah’s nephew George F. Bailey managed several shows, too, designing a tank in which a hippopotamus could be moved from place to place. Another nephew, Fred Harrison Bailey, recognized a potential circus skill in James Anthony McGuiness, later James Anthony Bailey, who united the Cooper and Bailey in the same way as Phineas Taylor Barnum’s circus to form the Barnum and Bailey Circus, which far along joined past the Ringling Brothers Circus to form the Ringling Brothers and Barnum and Bailey Circus.

Perhaps the first of the Northerners to tie in permanently in Fairfax County to farm was Lewis Bailey, an upstate New Yorker and the son of Hachaliah Bailey, who followed his dad south. In 1837, the elder Bailey bought hundreds of acres of Fairfax land, much of it on the outskirts of present-day Arlington County in the Place now known as Baileys Cross Roads. Shortly afterward, Lewis Bailey bought 150 acres (0.61 km) of house from his father for ten dollars an acre. Included in the buy was “a good dwelling-house,” but there were “no further buildings of value, and Tiny or no fence.” The farm itself, he wrote later, consisted of “cultivated worn-out lands, too destitute to build a crop of grass, or offer cultivation without manure.” Some of Bailey’s neighbors considered the farm the poorest in the vicinity. When he built his first little barn, twenty-four by thirty-six feet, they asked him if he “ever time-honored to fill it.” The question was scarcely a jest, for Bailey did not make tolerable hay the first year “to winter two horses.” Nevertheless, the buy was a wise one. Within a decade Bailey had a Good herd of dairy cattle and had become one of the more prosperous farmers in the area. The Baileys were prominent members of the Dulin Methodist Church, and intermarried subsequent to many Falls Church people