One of the busiest areas of Arlington can be found in Clarendon, where Washington Boulevard, Wilson Boulevard and Clarendon Boulevard all meet. In the early 1900s, the presence of the trolley in Clarendon led to an outgrowth of merchants and businesses in that neighborhood.

Although the names, owners and buildings themselves may have changed over time, what has remained constant is the steady parade of shoppers, pedestrians, and commuters that flock to the businesses and restaurants in Clarendon. Long before malls and multiplex cinemas became the mainstays of the present day consumer, customers packed the Ashton Theater, Little Tavern, Sears, and numerous other businesses in Clarendon.

Clarendon Circle was conceived around the time of the onset of World War I, when a parcel of land donated by Arthur J. Porter was used to make the circle.  Sometime in the late 1920s-early 1930s, the American Legion began construction on a War Memorial Monument in the center of the circle, supposedly using stones from a retaining wall from the Tomb of the Unknown Soldier, which was being dismantled at that time. After its dedication on November 11, 1931, the memorial remained at Clarendon Circle until 1940, when concerns about the structure being a possible traffic hazard resulted in its relocation to the Court House that same year. Eventually, in 1986, the memorial was returned to a spot very near its original location.