1] A new tree‐ring record from living and remnant bristle-cone pine (Pinus aristata) wood from the headwaters region of the Rio Grande River, Colorado is used in conjunction with other regional records to evaluate periods of unusually severe drought over the past two millennia (B.C. 268 to A.D. 2009). Our new record contains a multi‐century period of unusual dryness between 1 and 400 A.D., including an extreme drought during the 2nd century. Characterized by almost five decades of drought (below average ring width), we hypothesize this megadrought is equally, if not more severe than medieval period megadroughts in this region. Published paleoclimate time series help define the spatial extent, severity, and potential causes of the 2nd century megadrought. Furthermore, this early period of unusual dryness has intriguing similarities to later medieval period aridity. Our findings suggest we should anticipate similar severe drought conditions in an even warmer and drier future.