The Mary A. Gregory was built on Goose Island in 1875. She was purchased by Captain John Harry Woltman in 1894 and sailed by him until 1924. She was said to be the last of the trading schooners sailing the Great Lakes from the port of Chicago. She was rebuilt in 1920 by Captain Woltman at St. Joseph, Michigan. In 1924, after stripping her, Captain Woltman towed her into Lake Michigan and set her ablaze, a customary burial for retired ships, saving a few key remnants including the figurehead and bowsprit.
This figurehead is a rare artifact documenting early shipping in Chicago and the Great Lakes, and early industry at Goose Island in Chicago. The Mary A. Gregory hauled cargo across the Great Lakes to Chicago for over fifty years.