Fannie Lou Hamer was born in Montgomery County, and it was here in 1963 that she was nearly killed. On Sunday 9 June a Trailways bus carrying her and other voting-rights workers home from a voter education workshop near Charleston, South Carolina, stopped at the Winona depot and Staley's Cafe beside it. Euvester Simpson, 17, and Ruth Davis were turned away from the whites-only restroom; Annell Ponder, James West, Rosemary Freeman and June Johnson, 15, were refused service at the lunch counter. Police arrested them and took them to the Montgomery County Jail.
Hamer and several others were beaten, Hamer worst of all. Jailers made two Black prisoners, named in one account as Roosevelt Knox and Sol Poe, beat her with blackjacks, and she never fully recovered. The FBI photographed her injuries, and that December five white Winona officials were tried in federal court and acquitted by an all-white, all-male jury. In 1964 she described the beating to the Democratic National Convention.
The jail stood at Sterling Avenue and Oak Street; it closed in November 1998 and was torn down in 1999, and a historical marker now stands on the site. A second marker on North Applegate Street (US 51), near the old bus depot, was added in 2024 as part of the Mississippi Freedom Trail.
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