Records of terrestrial environmental change indicate that continental cooling and/or aridification may have predated the greenhouse-icehouse climate shift at the Eocene-Oligocene transition (EOT) by ca. 600 kyr. In North America, marine-terrestrial environmental change asynchronicity is inferred from a direct comparison between the astronomically tuned marine EOT record and published 40Ar/39Ar geochronology of volcanic tuffs from the White River Group (WRG) sampled at Flagstaff Rim (Wyoming) and Toadstool Geologic Park (Nebraska), which are type sections for the Chadronian and Orellan North American Land Mammal Ages. We present a new age-model for the WRG, underpinned by high-precision 206Pb/238U zircon dates from 15 volcanic tuffs, including six tuffs previously dated using the 40Ar/39Ar technique. Weighted mean zircon 206Pb/238U dates from this study are up to 1.0 Myr younger than published anorthoclase and biotite 40Ar/39Ar data (calibrated relative to Fish Canyon sanidine at 28.201 Ma). Giving consideration to the complexities, strengths, and limitations associated with both the 40Ar/39Ar and 206Pb/238U datasets, our interpretation is that the recalculated 40Ar/39Ar dates are anomalously old, and the 206Pb/238U (zircon) dates more accurately constrain deposition. 206Pb/238U calibrated age-depth models were developed in order to facilitate a robust intercomparison between marine and terrestrial archives of environmental change, and indicate that: (i) early Orellan (terrestrial) cooling recorded at Toadstool Geologic Park was synchronous with the onset of early Oligocene Antarctic glaciation and (ii) the last appearance datums of key Chadronian mammal taxa are diachronous by ca. 0.7 Myr between central Wyoming and NW Nebraska.