Anna McLaughlin Hardwicke Pennybacker was born on May 7, 1861, in Petersburg, Virginia to John Benjamin Hardwicke and Martha Dews Hardwicke. During high school, she dropped her given middle name “McLaughlin” in favor of the initial “J.”

When Sam Houston Normal Institute (SHNI) opened in 1879, Pennybacker took a competitive examination which won her the Peabody Fund Scholarship for her district and a place in the first class at SHNI. She was a student of distinction and was awarded the Peabody Medal for excellence. She graduated in 1880 and in the next few years worked as an educator in public schools in Texas and colleges in Missouri.

In 1884, she returned to Texas and married Percy Vivian Pennybacker, another member of SHNI’s first graduating class. She became principal of the high school in Tyler, Texas, and he the superintendent, roles which they would hold for nine years. Together, they had three children, Paul Bonner, Percy Vivian, and Ruth. During this time, they also conducted a Teacher’s Bureau and aided in the establishment of the State Teacher’s Association. In 1888, Pennybacker published “"A New History of Texas for Schools: Also for General Reading and for Teachers Preparing Themselves for Examination" which became an official public school text for forty years. Pennybacker became the superintendent of Palestine, Texas’ schools in 1895.

On May 15, 1899, Anna’s husband Percy Vivian Pennybacker died. He is buried in Oakwood Cemetery in Austin, Texas.

She was heavily involved in Women’s Clubs, which during this period were focused on community improvement, lobbying for things such as improved labor laws for women and children, safe food and drug laws, and municipal reforms.

In 1894, she founded the Tyler’s Women’s Club. From 1901-1902, she serving as president of The Texas Federation of Women’s Clubs from 1901-1902, during which she lobbied successfully for the funding of a women’s dormitory and raised $3,500 for scholarships for women at the University of Texas. She went on to hold several positions within General Federation of Women’s Clubs from 1904-1912 culminating in two terms as president from 1912-191. She heavily influenced the Chautauqua, New York, Women’s Club and was its president from 1917 to 1938.

She was additionally involved in political causes as the chairman of the Child Welfare Committee of the League of Women Voters (1920), and of the American Citizenship Department of the General Federation of Women’s Clubs (1920-1924). She was an associate member of the Democratic National Committee (1919-1920), through which she became good friends with Eleanor Roosevelt based on their common Demoncratic ideals, along with their interest in the advancement of women and world peace. She functioned as an unofficial political analyst for the Roosevelt campaigns, helping campaign officials gauge political sentiments in the southwest. In 1936, through her efforts, President Roosevelt would help fundraise $13,000 for the Chatauqua Women’s Club, and in 1937, Eleanor Roosevelt would become the first and only First Lady to speak at Sam Houston State University.

Pennybacker spent the latter half of her life travelling the country to lecture on causes such as the status women and immigrants, the World Court and the League of Nations, and Near East Relief. She was the first woman in Houston history to give the commencement speech to the city’s combined high schools (1937) and acted as a special correspondent to the League of Nations on several occasions (1925, 1926, 1927, 1931). During the later years of her life, she was additionally involved in the Foods Administration of Texas and the Texas Centennial Commission (1934). She died on February 4, 1938, in Austin, Texas, at the age of 77. She is buried in Oakwood Cemetry with her husband.