Frederick Law Olmsted's 1883 plan for South Boston's Marine Park envisioned connecting it to Castle Island by filling in about 600 acres of mudflats, a project that took nearly 50 years to achieve. A wooden footbridge built in 1892 first gave the public access to Castle Island and drew large crowds, with summer Thursday night dances held under a wooden canopy hung with colored lanterns. In 1896, an iron pier extended from the Head House toward what was then called Head Island and is now known as the Sugar Bowl, and across from Castle Island the pier helped define Pleasure Bay and advanced Olmsted's goal of increasing public access to the health benefits of sea air. The footbridge was replaced by a cement path across newly made land in 1928 and then by a paved road in 1932. A 1925 aerial view showed soil dredged from both the Reserved Channel and Pleasure Bay being dumped to create new land between Castle Island and South Boston, land that is now Massport's Conley Container Terminal. The 1938 hurricane heavily damaged the pier, which was replaced in 1953 by a granite causeway, and six years later Pleasure Bay was enclosed by a dike with two openings that allow the tide to flow in and out.
