The circle was built around 1890 by the Chevy Chase Land Company as part of its construction of the northern extension of Connecticut Avenue from the Rock Creek gorge.

The circle marks the lone bend in the road’s five-mile stretch between Rock Creek and its original terminus at Coquelin Run.

The company had initially planned to grade the road in a straight line to Rockville, Maryland, but could not acquire the necessary land at the desired price, and so turned due north at the D.C.-Maryland border.

A streetcar line—first named the Rock Creek Railway, later the Capital Traction Company—ran through the circle until Sept. 15, 1935, when its service was replaced by buses.

[2][3] The east and west sides of a grassy ring within the Circle's interior each contain a Garden Club of America entrance marker that denotes Connecticut Avenue's entry into the District of Columbia.