Connecting Grand and Drexel is the half-mile-long Oakwood Boulevard. Oakwood Boulevard intersects with Grand Boulevard at 39th Street and meets Drexel Boulevard at Cottage Grove. Today, Oakwood Boulevard is lined with newly constructed townhomes adjacent to the recently developed Mandrake Park.
Oakwood Boulevard was the original site of Henry McNeil "Mandrake" Brown's grassroots campaign to eliminate tobacco- and alcohol-related billboards that targeted African-American and Latino youths. He "whitewashed" the first billboard on Oakwood Boulevard in 1990. Brown was able to remove 700 billboards across the metropolitan Chicago area prior to his death in 1996.
Oakwood Boulevard is also home to Northeastern Illinois University's Carruthers Center for Inner City Studies. CCICS was established in the 1980s as part of the university's mission to meet the educational needs of Chicago's inner-city communities. Programs at CCICS are interdisciplinary and emphasize the complex ethnic and racial issues that impact the community.