Early Dupont Circle started out as a brickyard and slaughterhouse. The neighborhood creek, Slash Run, began near 15th Street and Columbia Road and ran from 16th Street near Adams Morgan, through Kalorama within a block of Dupont Circle. The Board of Public works under Alexander “Boss” Shepherd paved the way for the development of Dupont Circle. Nevada Senator William Morris Stewart led the “California Syndicate” that purchased tracts of undeveloped land. They quickly set about designing a fashionable neighborhood. Stewart set the standard by building his own grand mansion in the 1870s.

Many larger homes included carriage houses and attached servant’s quarters which were converted to apartments and rooming houses as the the upper-middle class moved on and affluent African Americans, including doctors and intellectuals associated with Freedmen’s and Howard University, replaced them. In the early 20th century, 14th Street NW rose to prominence as a main shopping district for Washingtonians as well as a location for automobile showrooms. The 14th and U Street area evolved into Shaw, encompassing parts of Logan Circle and U Street. The 1968 DC riots devastated the 14th Street commercial corridor and the Logan Circle neighborhood began a steep decline. During the 1980s and 1990s, despite its beautiful Victorian homes surviving the riots, Logan Circle was overrun with drug and prostitution activity and was widely considered unsafe. During the latter part of this period property values in the area increased along with the homeless population. 14th Street was known as Washington’s red light district and due to large commercial spaces previously occupied by auto showrooms and low rents, an avant-garde theater district. During the 2000s, the area rapidly gentrified and housing costs rose significantly. Neglected buildings were razed or remodeled. 14th Street and P Street saw major revitalization. Whole Foods Market opened two blocks from Logan Circle in December 2000, on a site previously occupied by an abandoned service garage. Since then, the area has continued to redevelop and increase in value and popularity.