From its earliest days, the Front was home to frequent organized baseball games and cricket matches, and to sledding and tobogganing in the winter, all of which drew large crowds to the park. Both the popularity of the Front and the desire to eliminate nuisances associated with the commercial use of the adjacent waterfront and canal side property caused the Park Commission to seek to acquire the lands between the Front and the lake. After a four year legal battle, the Front was expanded by a 20 acre waterfront addition in 1890.
Olmsted was engaged to draw up plans for the new addition in 1891. He proposed to make substantial use of the waterfront area, with a boat house, a public landing for small boats, a sheltered swimming area, separate gymnastic playgrounds for young boys and girls, and a scenic drive and walks. A new bridge over the Erie Canal and the railroad was built at the foot of Porter Avenue to join the new section of the park to the original portion. (Its ornate stone abutments now grace the Porter Avenue bridge over the Thruway. Before park development of the new area could begin, however, a great deal of land reclamation and filling had to be undertaken, which began as soon as the land was under Park Commission control.