The Annie Webster Papers at the Amesbury Carriage Museum (ACM) offer an intimate look into the remarkable life of Annie Webster, affectionately known as "The Boss." Her legacy as a community pioneer is preserved through this collection.

Annie E. Webster was born on December 9, 1879, in Salisbury, Essex County, Massachusetts, to Daniel Webster and Helen N. Collins. The couple had three children, but only Annie survived into adulthood. She lived in her family home at 54 Market Street.

Annie holds the distinction of being the first woman in Amesbury to serve as a selectman, to receive a driver’s license, and to operate her own automobile. She was elected as the first woman selectman in Massachusetts in 1933, receiving more votes than anyone in the town's history. She narrowly won re-election the following year and became Chairman of the Board of Selectmen in 1934.

Annie inherited her father’s market, "Webster’s Fancy Goods Store," at 24 Market Street, which she successfully ran for over 35 years. She also invested in real estate, owning the Webster Block, and also invested in the stock market. One of the first women to purchase an automobile, she received her driver’s license in 1908 and held it for over 50 years, even learning to be her own mechanic.

As the head of the Emergency Relief Administration (E.R.A.), Annie managed local improvement projects during the Depression, keeping many employed. She served as chairwoman of the Licensing Board and was involved with the E.P. Wallace Women’s Relief Corps and the Amesbury and Salisbury Agricultural and Horticultural Society. In 1955, she was appointed chairman of the Town History Committee, amassing a large collection of historical notes, printed materials, and photographs.

Annie was known for her compassionate community efforts. During the Depression, she and her friend Grace Carr distributed surplus milk and food to needy families. They also organized parties for local children, providing games, songs, and treats.

Annie's interests included fire trucks and automobiles. She drove firemen to fires in her Cadillac and regretted never driving a fire truck herself. Her first car was a 1909 Model-T Ford, and she continued driving into her 80s.

In her later years, Annie became a recluse, living with her pets at 54 Market Street. Upon her death on June 8, 1964, she left $15,000 to charities and educational institutions and the remainder of her estate to her pets. Her beloved cat Tippy lived to be about 25 years old. The Bartlett Museum houses a carriage once owned by Annie, a 1906 cut-under model by Amesbury’s Hume Carriage Company. Her bicycle, manufactured circa 1905 by Amesbury’s Eastern Cycle Company, (on permanent loan from Lester Grinnings,) is on display in the Industrial History Center.

Annie is buried at Mount Prospect in Amesbury under a large monument. The Annie Webster Papers at the ACM, which contain diaries, Sunday School record books, grange programs, and photographs from 1879 to 1964, offer a window into her unconventional life and community contributions.

• Biographical information in this article was taken from the research of Joyann Reynolds.