One of the ways that flappers rebelled against convention during the 1920s was by frequenting speakeasies and other private clubs where they could drink illegally. Previously, bars and saloons were considered an all-male space and respectable women did not drink in public. Even after Prohibition was over, Connecticut law made it illegal to serve a woman alcohol at or within three feet of a bar. 

During Prohibition (1919-1933), alcohol was still readily available in Connecticut. The coastline in Fairfield and Bridgeport provided direct access to international waters and ships that carried liquor from Europe, the Bahamas, and Canada. "Rum runners" used speedboats to deliver the liquor to networks along the Connecticut shoreline. Inland, bootleggers kept a steady supply of liquor flowing from New York and along the Post Road, and people distilled alcohol in homes, farms, and shops. Loopholes in the law enabled people to buy alcohol at a drugstore with a doctor's prescription, to make their own wine for family consumption, or to drink at a "speakeasy" that qualified as a private club.

Fairfield Women for Reform


Women were also active in the movement to repeal Prohibition, which gained steam as crime and corruption related to Prohibition became more widespread.  Fairfield's Annie B. Jennings and Sylvia O'Dwyer were among the leading "society" women who became active in the Women's Organization for National Prohibition Reform, which claimed more than a million members by 1932.  Using their influence and political ties, they helped make the cause of repealing Prohibition respectable.