Delia Webster (1817-1904) was the first woman to go to prison for her participation in the Underground Railroad, a system of safehouses used to help African Americans escape slavery. 

Born in Vermont, she was teaching school at 12 years old. She went on to get a college degree at Oberlin College in Ohio. She became very active in the abolitionist movement. She moved to Kentucky to teach. She met Rev.Calvin Fairbanks and became a conductor on the Underground Railroad. Webster called his attention to a man named Lewis Hayden who was trying to escape slavery. It is likely that Webster financed part of Hayden’s journey. 

They helped Lewis Hayden, his wife, and young son escape by carriage in 1844. They safely conducted the Haydens from the slave state of Kentucky to the home of Reverend John Rankin in the free state of Ohio. The Haydens continued their journey from house to house all the way to Canada. Fairbanks and Webster were later identified for their roles in the Hayden family escape. They were arrested and tried. 

Webster was sentenced to two years of hard labor at Kentucky State Penitentiary. Since she was the only female prisoner, she was housed in a wooden cottage in the center of the prison yard. She was visited by high ranking abolitionists and was celebrated as a martyr for the cause.The pro-slavery warden was very enamored of her and pushed for her to be pardoned in hopes she’d like him. After serving five weeks of her sentence, she was pardoned by Governor John Crittenden but on the condition that she publicly renounce her abolitionist sentiments. Upon release she returned to Vermont and published a pamphlet called, “Kentucky Jurisprudence: A History of the Trial of Miss Delia A. Webster (1845)”. She did not return the warden’s romantic sentiments and he was not happy that she spurned him. She later moved back south to Madison, Indiana, a town right next to the Kentucky border and continued her abolitionist activities. 

Lewis Hayden and his family eventually returned to the United States. Hayden went on to become an influential abolitionist, speaker, and politician in Massachusetts. The Lewis and Harriet Hayden house in Boston is a National Historic Site and part of the Black History Trail.

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