On November 10, 1897, she married Warren Wallace Beckwith, in Milwaukee, Wisconsin, at 2:30 in the afternoon. Beckwith was a member of the Mt. Pleasant Football Team and Jessie's father, Robert, strongly and bitterly opposed the couple's being together. He believed their relationship had ended until news of their elopement reached him and his family. He hurried to Jessie's room only to find it empty and that Jessie had married several hours before. In Des Moines County, Iowa in 1898, she gave birth to her first child, Mary Lincoln Beckwith (1898–1975). She continued to live in Mount Pleasant, Iowa, and on July 19, 1904, had her second and last child, Robert Todd Lincoln Beckwith (1904–1985), named after her father.