Winchester Black Heritage Trail

Walk through Winchester’s rich Black history on this self-guided heritage trail, where blue and yellow signs mark key moments of resilience, achievement, and community strength. Learn about Black-owned businesses that once thrived along West Washington Street, the impact of local leaders in civil rights and education, and the contributions of Black veterans and athletes.

Meet early Black residents like Fanny Cole, who became a successful businesswoman after her husband purchased her freedom. Discover the courage of Jennie Bibbs Didlick, who won a legal victory after refusing to move to the back of a bus—ten years before Rosa Parks made headlines.

More than just a walk through history, this trail highlights the everyday people who shaped Winchester, proving that powerful stories aren’t just found in textbooks—they’re found in the streets, homes, and lives of those who built the community.