Saturday, December 09, 2023
Entertainment, Parks

The Legend of Pleasure Beach

By Eric D. Lehman

 When the growing city of Bridgeport annexed the borough of West Stratford in 1889, it included a triangular island of thirty-seven acres which would become the stuff of legends in Bridgeport history.

Playing up the legend that Captain Kidd had buried treasure on this barrier island at the mouth of Bridgeport Harbor, liquor dealers J.H. McMahon and P.W. Wren turned the island into an amusement park three years later.

In 1905, the owner of Steeplechase Park on Coney Island in Brooklyn, George C. Tilyou, bought the Bridgeport park, now named Steeplechase Island for the unique ride in which carousel-style horses raced down a metal track.

Two years later, while the Chicago National League team and the Bridgeport team were warming up for a baseball game at the park, a dropped cigarette caused a fire that burned much of the park, including the eponymous “steeplechase” ride.

That gave birth to the island’s first legend: The two teams continued to play five innings as the park burned up, hitting foul balls into the smoldering ruins of the bleachers.

Tilyou sold the park in 1910 and it was renamed Sea Breeze Island. However, attendance was poor and the park closed for several years.

Then, in 1919, the city bought the park, and expanded and improved it. Boardwalks led to a carousel, a roller skating rink, a miniature railroad, a roller coaster, and “The Old Mill” ride that became a popular tunnel of love. The Brickerhoff Ferry brought visitors directly from a dock downtown, and in 1927 a long bridge over a sandy causeway allowed foot and automobile access to what was now called “Pleasure Beach.”

The maple dancing pavilion with bell towers and glass sides became the biggest attraction, featuring the largest ballroom in New England. Stars of the Jazz Age like Gene Krupa, Glenn Miller, and Artie Shaw played here, and thousands of young people flocked to dance on the beautiful maple floor.

A fire in 1953 damaged the roller coaster and a few other rides. Five years later, the amusement park was sold again, but a year later closed for good. The abandoned beer garden later became the home of the Polka Dot Playhouse in 1967. The dance pavilion burned down in 1973, effectively ending the island as a destination.

In 1996 the bridge from the mainland burned, seasonal homes were abandoned, and the Polka Dot Playhouse relocated downtown, renaming itself Playhouse on the Green.

Today, the park has a more unfortunate legendary status: It’s the state’s largest ghost town. The only ones who enjoy amusement at Pleasure Beach are piping plovers. The island is now a protected refuge for endangered birds and plants like the prickly pear cactus.

No one ever found Captain Kidd’s gold, but today the treasure of Pleasure Beach is buried in the memories of Bridgeport’s citizens.

Want to learn more about Pleasure Beach? The Bridgeport History Center has the following materials available:

  • Bridgeport: Tales from the Park City. By Eric D. Lehman (Charleston, SC: The History Press, 2009.)
  •  Bridgeport on the Sound, by Mary K. Witkowski and Bruce Williams.  Charleston, S.C.:
[974.691 B85wi]
  • Arcadia Publishing, 2001
  • Newspaper Clippings, Bridgeport History Center:  “PARKS – Pleasure Beach”
  • Vertical File, Bridgeport History Center:  “PARKS – Pleasure Beach”
  • Manuscripts Collection, Bridgeport History Center, various topics
  • Bridgeport General Photograph Collection, Bridgeport History Center, various images
  • Postcard Collection, Bridgeport History Center, various images
  • The Story of Bridgeport, by Elsie Nicholas Danenberg; illustrations by Jesse Benton.  Bridgeport, Conn.:  Bridgeport Centennial, Inc., 1936
[974.691 85d]
  • Bridgeport:  a Pictorial History, by David W. Palmquist; design by Jamie Backus Raynor.  Norfolk, VA:  Donning, 1981; 1985
[974.691 B85p]
  • A History of the Old Town of Stratford and the City of Bridgeport, Connecticut, by Rev. Samuel Orcutt; published under the auspices of the Fairfield county historical society.  New Haven, CT:  Tuttle, Morehouse & Taylor; published under the auspices of the Fairfield County                 Historical Society, 1886. 2 v. (viii, 1393 p.):  ill., plates, ports., folded maps ; 26 cm.

Notes:  Vol. 2 contains also histories of Huntington, Trumbull and Monroe, towns incorporated from old Stratford. Epitaphs from the various cemeteries are included.

Genealogies:  v. 2, p. 1113-1358.

[974.691 B85O2]
  • History of Bridgeport and Vicinity / ed. by George C. Waldo, Jr.   New York; Chicago:  S.J. Clarke Pub., 1917.  2 v., plates:  ill., ports. ; 28 cm.
[974.691 B85w]
Eric Lehman
Eric D. Lehman teaches creative writing and literature at the University of Bridgeport, and is the author of several books, including Bridgeport: Tales from the Park City; Becoming Tom Thumb: Charles Stratton, P.T. Barnum and the Dawn of American Celebrity; Afoot in Connecticut: Journeys in Natural History; and A History of Connecticut Wine; and ; A history of Connecticut food : a proud tradition of puddings, clambakes and steamed cheeseburgers. You may contact him at