A new genus and species of eurypterid (Eurypterida: Chelicerata) is described as Orcanopterus manitoulinensis from the Upper Ordovician Kagawong Submember (Upper Member) of the Georgian Bay Formation, Manitoulin Island, Ontario, Canada. The material comprises several partial specimens in addition to disarticulated carapaces, appendages, metastomas, opisthosomal segments, and telsons. Associated fossils include rare bryozoans, a conularid, ostracodes, and conodonts. A restricted marine lagoon, or very shallow subtidal to intertidal environment is inferred. This assemblage, perhaps representing an accumulation of molted exuviae, was apparently preserved as the result of rapid burial by carbonate muds and silts during a storm event. O. manitoulinensis shares a number of traits with both the Hughmilleriidae and the Carcinosomatidae. Diagnostic features include curved preabdominal segments, a petaloid A metastoma with deep anterior emargination, spiniferous appendages of Carcinosoma type, paddle with enlarged, symmetrical podomere 9, and a xiphous telson. It is only the fourth (the first Canadian) well-documented Ordovician eurypterid genus, and provides the oldest reliable record of the Hughmillerioidea to date.