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Upon hearing of her husband's death in the Seminole War in 1837, Ann Hawkins Gentry declared, "I'd rather be a brave man's widow than a coward's wife." Throughout her life in Boone County, Ann Hawkins Gentry personified the courage and grace so common among pioneer women.

She was born in Madison County, Kentucky in 1791 and married Richard Gentry in 1810. The Gentrys came to Boone County in 1816 and operated a tavern, first in the town of Smithton, then on Broadway in Columbia.

The Gentrys had four sons, five daughters and four children who died in infancy. While Richard was away on merchant expeditions to the American west or was fighting in the Black Hawk and Seminole Wars, Ann bore the burden of taking care of the children, running the tavern, operating Columbia's post office, and overseeing the family's other interests in Boone County.

In 1837, Ann Hawkins Gentry was appointed Postmistress of Columbia, replacing her deceased husband who had fallen at the Battle of Okeechobee. She remained in this position until 1865.

During the Civil War, she was an outspoken advocate of the Union, despite the fact that many of her children sided with the Confederacy.

Ann Hawkins Gentry died on January 18, 1870 and is buried in the Columbia Cemetery. A middle school and municipal building in Columbia are named in her honor.

In 1995 Anna Hawkins Gentry was inducted into the Boone County Hall of Fame, Boone County Historical Society.