U.S. Highway 99 is often coined the Golden State Highway and the Main Street of California. The road originally extended from the U.S.–Mexico border all the way to the Oregon border while passing through the Central Valley. When you travel along this route, you pass a little over half of all California prisons. By using U.S. Highway 99 as an entry point, this Article is a topographical study of California’s carceral history. The first Part of this Article gives a brief history of the various forms of incarceration—from California’s gold rush era in 1949, to the massive multimillion-dollar prison expansion during the 1980s and 1990s. The second Part narrates the carceral landscape that surrounds U.S. Highway 99 when you are driving along the route, starting from the Calexico East Port Entry near California’s southern border and following the original road all the way to the north where the road eventually traces the Siskiyou Trail. Intertwined with this narration is a description of the various ways California has disproportionately incarcerated communities of color and how the reliance on carceral practices affects education.