• Jackson Park
• Midway Plaisance
• Former Strand Hotel site
• Shrine of Christ Church

Woodlawn traces its earliest identity to a small community of Dutch farmers who settled in the mid-19th century, remaining largely rural with fewer than 1,000 residents until Chicago selected neighboring Jackson Park as the site of the 1893 World's Columbian Exposition. The Fair transformed the area almost overnight, bringing hotels, apartment buildings, and an elevated rail extension along 63rd Street that drew University of Chicago faculty and thousands of new residents in its wake.

By the 1950s, Woodlawn's population had grown predominantly Black as families arrived from the Great Migration, and 63rd Street became famous for its jazz clubs. Jackson Park, designed by Frederick Law Olmsted and connected to Washington Park by the Midway Plaisance, remains the community's crown jewel and today includes the site of the Barack Obama Presidential Center.

For anyone whose family called this South Side community home through its many chapters, MY-NHD's Woodlawn tee is a way to carry that history with you.