Why has no figure to compare with Iain Sinclair or Nick Papadimitriou emerged from North America? The standard histories, such as they exist, generally date the emergence of psychogeography to the Situationists in 1950s France. It's just as easy to find examples where the idea is credited, albeit in less specific terms, to a whole host of literary and historical characters: DeQuincey, Blake, Baudelaire, or even John Dee. Regardless of your opinion as to its origins, it seems that psychogeography as it's being practiced, discussed, and written about in the current decade is decidedly a British phenomenon. The concept has crossed the Atlantic but when encountered on American soil it tends to take the form of action based experiments or games (PIPS or Conflux, for example.) American psychogeography overall is missing that deep literary awareness and sense of history that makes its British counterpart so appealing. Could this be due to many Americans' innate sense that America is just too young to provide material as deep as that available to our British cousins? North America has a rich tapestry of homegrown literary and historical sources to draw on for inspiration and American psychogeography would be well served if practitioners began exploring them, a deep immersion into our own past as a filter through which to view the landscape.
A possible place to start thinking about this problem would be to consider the American landscape from the perspective of the original natives. The physical evidence of native history is all around us: burial and effigy mounds, "marker trees", petroglyphs, and even the ruins of ancient pueblos. There is also evidence of a more liminal nature left in the folklore and tales of the surviving descendants of those ancient tribes. There is much work to be done in recovering what knowledge we can about how the natives saw the land, and their idea of borders and boundaries. There are also places that are important in the standard Eurocentric histories in which natives play a large role: Little Big Horn, The Trail of Tears, or the Robledo Mountains in southwest New Mexico where Geronimo is said to have hidden out from US cavalry troops. Any of these offer nearly limitless paths for exploration.
The European settlers who we now call Americans have left their own stamp on the continent and it should not be difficult to find historical items that provide inspiration for further investigations. Daniel Boone's explorations in Kentucky, John Brown's trip from Harper's Ferry to Charles Town where he was tried and later hanged, or the remains of one of America's many 19th century canals are all examples of terrain that is as of yet unexplored in this realm. The list of American writers whose lives and work should be informing the American psychogeographer is nearly endless: Emerson, Thoreau, Melville, Kerouac, Steinbeck, Hemingway, and Poe (who himself is often mentioned as an ur-inspiration by the Europeans.) There are also a handful of living writers who belong on this list, like Paul Auster whose City of Glass should be a part of any serious psychogeographical library.
Salem with its witch trials, the simulacrum we call Disneyland, or the fact that Jack Kerouac once wrote eloquently about the water tower in North Platte, Nebraska, are all possible points of departure for psychogeographic work. Inspiration is all around us, whether it emanates from single points on a map like those already mentioned, lines on a map like New England's Great Road or the original route of the Mormon handcart pioneers, or a wider dispersal of geographic points like "towns in North Dakota that have mosques".
Deep immersion in our own liminal geography is the only way that American psychogeography will find its own identity. If American psychogeographers begin applying this deep immersion to their work, and sharing it via pen or camera, it's nearly inevitable that a few strong voices will emerge, voices which have the power to transmute the connection between history, literature, and landscape into a psychogeographic mythos that is distinctly American.