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Bailey's Crossroads draws its name from the Bailey family 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 still in New York state, he purchased an Indian elephant which was one of the first such animals to reach the United States.

Seeking a place to winter his circus animals, he moved to Virginia, and on 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 house 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 part of the Bailey family business. Hachaliah's son Lewis Bailey (1795–1870) operated a travelling circus and pioneered the use of canvas circus tents before 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 talent in James Anthony McGuiness, later James Anthony Bailey, who united the Cooper and Bailey with Phineas Taylor Barnum's circus to form the Barnum and Bailey Circus, which later joined with the Ringling Brothers Circus to form the Ringling Brothers and Barnum and Bailey Circus. Perhaps the first of the Northerners to settle permanently in Fairfax County to farm was Lewis Bailey, an upstate New Yorker and the son of Hachaliah Bailey, who followed his father 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 area now known as Baileys Cross Roads. Shortly afterward, Lewis Bailey bought 150 acres (0.61 km2) of land from his father for ten dollars an acre. Included in the purchase was "a good dwelling-house," but there were "no other buildings of value, and little or no fence." The farm itself, he wrote later, consisted of "cultivated worn-out lands, too poor to produce a crop of grass, or pay for cultivation without manure." Some of Bailey's neighbors considered the farm the poorest in the vicinity.

When he built his first small barn, twenty-four by thirty-six feet, they asked him if he "ever expected to fill it." The question was scarcely a jest, for Bailey did not make enough hay the first year "to winter two horses." Nevertheless, the purchase was a wise one. Within a decade Bailey had a fine 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 with many Falls Church people