North Brentwood was originally part of the “Castle Tract”—later known as the “Highlands”—which was owned by Captain Wallace Bartlett. In 1887, Capt. Bartlett dedicated a low-lying part of the land to the memory of the black regiment that served under him in the Civil War. He sold lots there to African-Americans, reserving some for the building of churches and schools. The first settlers were members of the Randall family, for whom the area was named. When the first school in Randall Town was opened in 1902, Henry and Peter Randall were the trustees.
In 1904, Capt. Bartlett’s company added a 40-acre subdivision to the community, naming it “Brentwood” after the Brent estate in northeast Washington, D. C. In 1907, William Conway organized The Brentwood Colored Citizens Association, whose purpose was to provide its members with opportunities to engage in educational, scientific, literary, musical, social, and other beneficial pursuits.
In 1905, Jeremiah Hawkins purchased several lots in the town, built a house for himself on one of them, and became politically active. He was elected as a delegate to the Republican National Convention in Kansas City in 1920. Under his leadership, the community was incorporated as North Brentwood in 1924. He became the town’s first mayor.
