Pleasure Beach is perhaps the one park left that is a sad reminder of the demise of the premier summer resorts of New England dating from the Gay ’90s. Tourists from throughout the northeast traveled by trolley and ferryboat to visit the original 37-acre area also known as the “Million Dollar Playground.” J.H. McMahon and P.W. Wren, two wholesale liquor dealers and land developers, turned the barren, sandy island into an amusement park in 1892. Three years later, a brochure of Pleasure Beach advertised a roller coaster, boardwalk, miniature railroad, skating rink, arcade, merry-go-round, a 5000-seat coliseum, wooden horse rides on a rail (for which the park later took the name Steeple Chase Island before returning to its original name) and a track that was one of the prestigious stops on the bicycle racing circuit. It also boasted of the Pleasure Beach legend, which alleges that the island was chosen by Captain Kidd for burying vast treasures.
No exorbitant prices, an honest dollar’s worth for all,” was the motto. The Pleasure Beach Cafe served broiled lobster and soft-shell crab for 50 cents, broiled bluefish for 40 cents, and clams on the half shell (when local oyster beds were abundant) for 25 cents a dozen.
McMahon and Wren, as well as other private operators, ran into some financial troubles with the help of the fires that have cursed the island through the years; the first came on August 18, 1907, and destroyed the grandstand and weaving horse rail ride. The Bridgeport Board of Park Commissioners bought the park for $220,000 in 1919 and took over full operation in 1938, running the park during its most glorious days. Through the Depression it was a place to relax–on the glittery carousel, roller coaster or in the big-band ballroom. In its heyday, Pleasure Beach attracted hundreds of thousands each year. In the 1950s the amusement center began to falter through the city’s willingness to allow it to deteriorate and due to declining tourist revenues.