The Late Mississippian was a critical time interval in Laurentia's history, marking the transition from carbonate deposition on a stable platform, during the Early to Middle Mississippian, to extensive clastic deposition in the Pennsylvanian to Permian associated with the Laurentia‐Gondwana collision. In the U.S. midcontinent, Chesterian incised valley fill (IVF) systems that developed within a carbonate‐dominated platform provide new insights on the patterns and drivers of continental‐scale sediment dispersal during this transitional period. Here we report 1,037 new concordant detrital zircon U‐Pb ages from nine samples of Uppper Mississippian sandstone collected from cores in southwestern Kansas and from outcrops in northwestern Arkansas. The sandstones are characterized by major age clusters corresponding to the Grenville (900–1,300 Ma) and Taconic‐Acadian (350–500 Ma) orogenies and minor older age groups, suggesting derivation from the Appalachian region. A compilation of published detrital zircon ages from Early Paleozoic sandstones as well as from temporally equivalent units across North America, including from the Appalachian Foreland Basin, Illinois Basin, Arkoma Shelf, Ozark Dome, Black Warrior Basin, and Grand Canyon, suggests Chesterian sandstone age distributions are distinct from those of older sandstones and are consistent with a change to a dominantly Appalachian age signature that was roughly synchronous across the continent. Together, the new and compiled ages support development of a generally E‐W transcontinental sediment dispersal system in the Late Mississippian that was likely controlled by orogenesis on the eastern Laurentian margin, while local variations in the age signatures appear to be controlled by N‐S drainage networks, influenced by glacioeustatic fluctuations and local structures.