The Eocene to Miocene Cypress Hills Formation (CHF) spans 28 million years and forms the conglomeratic caprock of the Cypress Hills and Swift Current plateaus in southwestern Saskatchewan and southeastern Alberta. These stacked fluvial, floodplain, and lacustrine deposits preserve the only high latitude, non-polar mammalian fossil assemblage (Uintan to Hemingfordian land mammal stages) in Canada. The Quarry is the oldest CHF (Chadronian 1, late Eocene) site documented in the Cypress Hills region north of the town of Eastend. The Quarry was originally discovered in 1962, after bones were found to be eroding out of the base of a road cut north of the ghost town of South Fork on the southeastern flanks of the Cypress Hills. Numerous field campaigns have resulted in the collection of fossils from a multitaxonomic bonebed. This paper presents a detailed sedimentologic, paleontologic, and taphonomic study to establish a depositional environment framework of the Southfork Quarry. This site was deposited at the onset of the Eocene–Oligocene climate transition, a critical time of climate change during the Paleogene. Six facies and two facies associations are characterized for the Quarry, shifting from a braided-fluvial system to a debris flow-filled incised channel. Patterns of skeletal accumulations and bone surface modification indicate that the assemblage accumulated over a significant interval of time in different depositional environments. This study provides critical insight into environmental shifts driven by climate change and relates these findings to a broader understanding of the Eocene–Oligocene transition in North America.