The 14th annual 5k run/walk is on Sunday, October 5, 2025, at 9 am. The course starts in Union Square Park and winds through and around Southwest Baltimore's historic landmarks and parks, including Hollins Market, the Irish Railroad Workers Museum, the B&O Railroad Museum, the Mount Clare Museum House in Carroll Park, and the H.L. Mencken House and Museum. The course showcases SOWEBO’s rich cultural diversity, architectural beauty, historic landmarks, and parks. Race participants enjoy refreshments and music during the awards ceremony in historic Union Square.