Few grazing themes so endure yet are so difficult for outsiders to document with certainty as historical and current-day livestock grazing routes: stock driveways. Excursions from one biome, ecotone, or landscape to another –in general, undertaken to seasonal cues – allow livestock owners and their hired herders to exploit different environments that offer notable advantages in terms of freeing livestock from unvarying diet, overtaxed grazing grounds, common diseases, and cycles of drought or drenching rain. Movement at whatever scale permits herders or shepherds an escape from monotony when they shift grazing grounds to montane-woodlands or back to lowland environments in travel that benefits both jaded humans and husbanded animals. Significant economic and ecological advantages accrue from the shifts of seasonal silvopastoralism, but the terrain, and in particular the routes animals travel, often stretch across varied land ownerships, and sifting out rights of passage is an ethnographic adventure requiring longstanding observation and consistent fieldwork. Formal scholarship about the road between is less established than literature of “the trail,” which is a staple feature of folklore, film, and fiction. As concern grows about the energy costs of using highways or railroads to move livestock, attention returns to traditional practices and legal accommodations that make possible trailing livestock under their own power. Across Europe are 4 million ha of land associated with livestock driveways, once widespread in the United States as an item of Spanish-Mexican heritage. This synthesis focuses on livestock driveway establishment in two landscapes: Spain and, secondarily, the western United States of America, with an overarching theme of how stock driveways can connect ecosystems and, by sustaining customary use, knit together silvopastoral society.