Ann Montgomery was born in Americus, Georgia and soon after, she moved to Los Angeles, California with her parents. Montgomery attended school in Los Angeles and Texas before moving to Buffalo, New York in 1910.

Once Montgomery moved to Buffalo, New York, she opened an ice cream parlor on Michigan Avenue which closed in the early 1920s. Then she opened a billiards hall on Michigan Avenue. Montgomery then bought the building and opened Ann Montgomery’s Little Harlem Hotel known as Buffalo's Queen of Cabaret. A few years later, she opened a nightclub in the Little Harlem Hotel. During this time from the 1920s and 1930s, Montgomery and her husband Dan were one of the most prominent couples in Buffalo who owned restaurants, hotels, and a nightclub.

Overtime Montgomery became a member of the Buffalo Chapter of the NAACP, the Michigan Avenue YMCA, and the Hadji Court 62 Daughters of Isis. She was also a supporter and giving sponsor to the Boys Club of America, the Negro College Fund Foundation, the Salvation Army, and the United Way of Buffalo and Erie County. As well as Catholic Charities, the Police Athletic League, and many other community organizations helping young people obtain jobs at her establishments so they could finish their education. 

Gloomily, Ann Montgomery passed away on April 11, 1978 at 87 years old.