George C. Tilyou, the well-established owner of Steeplechase Park at Coney Island, decided to extend his amusement holdings at the turn of the century. First he bought Steeplechase Pier in Atlantic City, and then turned his attention to Bridgeport, purchasing Pleasure Beach in 1905 and opening it as Steeplechase Island that season.

Patterned after his Coney Island attraction, Tilyou landscaped the park adding beautiful floral gardens, installed the famous Steeplechase race course ride, a bright new carousel, aerial swings, a figure eight roller coaster, Ferris Wheel, shooting gallery, the Razzle Dazzle Funhouse, skating rink, toboggan ride, penny arcade, bandstand, vaudeville theater, miniature train, a billiards room and an extensive lunch pavilion.

A mammoth ballroom dance floor was constructed of the finest maple available and the south side of the room was encased with mirrors. Thousands of light bulbs provided a brilliant appearance for the dancers after dark.

The steamboats, Lenoir, Media and Lizzie H. made regular trips from the Stratford Avenue wharf, along with ferry boats from a slip located at the foot of Seaview Avenue.

Opened in 1905, Tilyou operated Steeplechase until 1910 when it was sold.

By 1912, the name was changed to Sea Breeze Island. Many big promotions were used that year. On one day alone over 25,000 tickets were used by newspaper boys from all over Connecticut. Despite the many promotions, business was not good and the park was closed for a number of years.

Acquired by the City of Bridgeport for recreational purposes,the original name, Pleasure Beach was reinstated. In 1921 the property was leased to the well-known amusement building company, Miller& Baker,Inc. Apparently the venture did not turn out as expected when the ferry boats operated poorly and the trolley service did not do much better. By 1921, the park was in hands of receivers and in 1923, its assets were sold to creditors.

Despite the setback, Miller& Baker brought a new era to amusement park design, as they were responsible for most of the new construction. The Sky Rocket roller coaster was completed in 1922 with Fred W. Pearce,General Manager of Josiah Pearce& Sons construction company,the owner. Two Miller dome roof buildings were erected to house a carousel owned by Timothy Murphy,and a scrambler for S.B. Weisberger. A spectacular 268 foot long by 104 foot wide dance hall without a post in the entire span, capable of accommodating 2000 couples at a dance, was also new. Four new riding devices were completed for the Krug Brothers.

The exciting Dodgems were introduced in 1921 and in 1926 the newer version, Dodgems Jr. were being used. The pride of the park was a 4-abreast Carmel/Dentzel/Murphy Carousel carrying beautiful hand-carved and decorated horses and chariots.

During the rest of the 1920's and early 30's various Bridgeport management organizations controlled the park through leases to individual operators. But, the Depression took its toll and by 1937 the facility was in receivership and it became necessary for something drastic to be done. In an unusual civic venture,the City of Bridgeport voted to run Pleasure Beach as a business enterprise.

On Memorial Day, 1938,amid ribbon-cutting ceremonies, boat parades, speeches, music by the WPA band and high anticipation by Bridgeport politicians, a refurbished Pleasure Beach reopened as a business for the people, by the people and for the people.

New major attractions included a filtered 150 foot salt water swimming pool and the 'Shore House', a pleasant refined restaurant. Russ Morgan and his Philip Morris Radio Orchestra played the season opener at the dance pavilion.

Buster Crabbe's Water Follies performed at the pool during the 1946 season giving four shows daily.

The real downfall of Pleasure Beach began in 1953 when a bad fire caused considerable damage to the roller coaster and other attractions. Although business was good for a number of years,the park ran in the red for 20 straight years and in 1958, Bridgeport wanted out of the business and leased the property to Bert Nathan and Frank Sunshine.

Pony rides,hot rod cars and a looper ride were added to existing amusements, but by December 1959 the new owners were in financial trouble.