Bailey's Crossroads is a census-designated place (CDP) in Fairfax County, Virginia, United States.

[5] The opening months of the American Civil War proved to be a disruptive and unforgettable episode in the history of Bailey's Crossroads.

[6] Once Confederates established themselves atop Munson's Hill they built a crude fort there, and from these commanding heights turned Bailey's Crossroads into a "killing field".

Official reports on the 'War of the Rebellion' indicate that during August 28–30, 1861 a series of skirmishes took place at a location scrawled as "Balley's Cross Roads".

Thousands of Union troops marched in formation and paraded before President Abraham Lincoln, the northern press, and many onlookers from Washington.

Army commanders selected Bailey's Crossroads as the site because of its nature as a large, unbroken plain.

In order to prepare it for the day's activities the army merely needed to remove the split-rail fencing separating farms and fields.

The area remained a rural farming community until the post-World War II years, when a massive wave of development occurred.

A strip shopping center called Culmore, in particular, has lent its name to the apartment development behind it, which is now home to several thousand Latino immigrants.

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.

[12] According to the United States Census Bureau, the CDP has a total area of 2.0 square miles (5.3 km2), all of it land.

This unbroken expanse of level ground caused the Union Army to select it as the site of a massive review of troops during the Civil War.

The review, which took place on November 20, 1861, involved thousands of troops marching in formation and parading before President Abraham Lincoln.

The most noticeable landmark at Bailey's Crossroads is Skyline Center, a towering group of 26-story apartment buildings and offices built in the 1970s.

While the closest Metrorail station is a few miles away, Metrobus service on the Columbia Pike corridor has recently been improved.

Current discussions among the Fairfax County government for revitalizing Bailey's Crossroads economically concern themselves with the Fairfax County border on the north and east—which generally includes all commercial and residential properties generally considered as belonging to the neighborhood—as well as Seminary Road and Carlin Spring Road.

[11] As a general neighborhood, however, with all facets of life included, the geographic extent of Bailey's Crossroads must be considered to be larger.

North of Leesburg Pike its extent is generally defined by Glen Carlyn and Carlin Springs roads.

[14][15] A United States Post Office, located in Culmore, serves the Bailey's Crossroads ZIP code of 22041.

[16] At the 2020 census (some information from the 2022 American Community Survey) there were 24,749 people, 9,796 housing units and 9,545 households residing in the CDP.