On the afternoon of June 25, 1909, Booker T. Washington, the most famous African American leader of the early twentieth century, delivered a speech in the town of Christiansburg, Virginia, located along the Transamerican bicycle route 76. An exploration of the history of Booker T. Washington’s visit to the Christiansburg Institute provides a basis for exploring the complex relationship between race and education in Virginia during Jim Crow segregation while also making connections to current issues related to identity, opportunity, and equality. This episode is connected to the town of Christiansburg, located just over 350 miles from Yorktown, the starting point for the westbound route, and just under 200 miles from the Kentucky border, where eastbound rides enter Virginia.