Revisiting approaches to historical geography is an activity favored by many, and this essay provides a journey through space and time. After an introduction, I shift to look at seven separate if succinct examples, with illustrations looming large as a reminder of just how significantly historical geography differs from straight-up academic history, whether in an approach to fact or in its historiography. Presented are scenes and circumstances that matter to me, each incorporating a moment or two of memoir. Themes include movement (conveyances); extraction (mining); management (working landscapes); routes (byways); vernaculars (licit and illicit); edibles and farmways; and, finally, cooperation—the last a look at whom we learn from in the field. The overall message is a plea for researching a past that reminds us that the more things change, the more they stay the same.