Little is known about Williams's early years in Trinidad. A devotee of calypso, she published a booklet in 1959 entitled "12 Songs from Trinidad" which included two songs about the British West Indian labour unrest of 1934–39 oilfield strike in Trinidad: 'King Flecky' and another based on the World War I calypso "Run Your Run Kaiser William".[9]
In 1943 the Calypso Restaurant opened, first located at 146 MacDougal Street, and James Baldwin was hired as a busser and dish washer. The restaurant later moved to 51 MacDougal Street. Early in Baldwin's career at the Calypso he met artists, writers, and activists such as Beauford Delaney (the modernist painter who introduced James Baldwin to Connie Williams in 1943), Marlon Brando (then an acting student), and labor organizer Stan Weir (academic). With the encouragement and support of Williams and Delaney the young Baldwin developed as a writer and intellectual.[8] Williams remained friends with Baldwin throughout his life, hosting a birthday party for him on 20 May 1963 at her San Francisco restaurant on Fillmore Street.[1][10] Connie took the young James Baldwin 'under her wing'.[11][12][13][14]
Other artists, performers, and intellectuals who frequented The Calypso included Henry Miller, C. L. R. James, Tennessee Williams, Eartha Kitt, Paul Robeson, Richard Wright (author), Grace Lee Boggs, and Paul Robeson.[6][15][16]
During and after the U.S. calypso boom which peaked during WWII, Williams promoted many prominent calypsonians and bandleaders in New York City—Gerald Clark, MacBeth the Great, Lord Invader, Wilmoth Houdini, The Duke of Iron, and others—whom she hired to play at holiday dances and carnival balls. These events also featured dancers such as Ismay Andrews and Pearl Primus. [17]
In 1962 Connie founded Connie's West-Indian Restaurant in San Francisco's Haight Ashbury. The restaurant was a favorite for black intellectuals and, like her West Village restaurant, was frequented by James Baldwin when he came to San Francisco.[18]
In 1969, Connie's Restaurant relocated to 1909 Fillmore St in San Francisco after the Hippie "invasion" of Haight-Ashbury.[19]
In 1976 Connie organized the first carnival in San Francisco.[20]
Connie was the founder of Carijama Oakland Carnival, a San Francisco Bay Area carnival begun in the 70s. She was also one of the founders of the Carnival West Coast Caribbean Association.[2][21][22][23]