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In 1867 the U.S. Bureau of Refugees, Freedmen, and Abandoned Lands (popularly known as the Freedmen's Bureau) created Barry Farm—a post-Civil War community of formerly enslaved and free persons. The Bureau acquired 375 acres of land from David and Julia Barry, white landowners. The plan was to sell or lease lots for black housing and use the proceeds to fund education at the same time. The acreage was subdivided into approximately one-acre lots and sold on installment plans or leased.

Many of the new residents came from alley slums in Georgetown and Washington City, the only places they could find to live in freedom. By 1870 more than 500 families had made Barry Farm their home and had started creating a community. Families worked in the city by day and built their homes across the river by night. Macedonia Baptist Church and Mt. Zion Hill School were the first institutions built by residents; the school's lot was purchased with Freedmen's Bureau funds generated by land transactions. The community was renamed Hillsdale in 1871.

During World War II the U.S. Government constructed "Barry Farms" housing on Hillsdale's eastern edge to relieve overcrowding across the Anacostia River. Soon urban renewal in Southwest brought more families, spurring the overbuilding of multifamily housing. These projects, along with the Suitland Parkway and Anacostia Freeway, greatly changed the neighborhood.

Several of Hillsdale's early houses still exist, especially along Elvans Road, SE, but most have been razed and replaced with more modern structures.

Barry Farm Site is bounded by St. Elizabeths Hospital, Alabama Avenue and Morris Road, SE, and the Anacostia River