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.

From the time of its incorporation until the 1940s, North Brentwood was home to many privately owned businesses. Among them was a dairy, a coal yard, an ice house, beauty and barber shops, grocery stores, restaurants, a private school, and a shoe repair shop.

The North Brentwood Historical Society, organized by Lillian K. Beverly in 1991, developed a comprehensive oral, pictorial, and artifact collection defining life in North Brentwood from the early 1900s to 1930. The exhibit, entitled Footsteps from North Brentwood, was displayed at the Anacostia Smithsonian Museum in 1996. The following year, portions were displayed at the North Brentwood Community Center and at the State House in Annapolis. Currently, the mayor and town council are exploring ways to create a town museum to house the collection. The desire is to create a focal point that will amplify awareness of the town’s heritage among the residents and encourage participation in the arts.

North Brentwood always has had dedicated, civic-minded citizens who organized, voted, and persevered in adversity to build the worthy town that it is today. That tradition of social and civic involvement is still alive and thriving in the current citizenry of North Brentwood.