Despite the centrality of the idea of history to Dewey's overall philosophical outlook, his brief treatment of philosophical issues in history has never attracted much attention, partly because of the dearth of the available material. Nonetheless, as argued in this essay, what we do have provides for the outlines of a comprehensive pragmatist view of history distinguished by an emphasis on methodological pluralism and a principled opposition to thinking of historical knowledge in correspondence terms. The key conceptions of Dewey's philosophy of history outlined in this paper -- i.e. historical constitution of human nature, constructivist ontology of historical events, as well as the belief that the proper form of historical judgments is underwritten by the category of continual change -- are discussed with a view to the current challenges in philosophy of history, e.g. the contest between naturalism and rationalism, objectivity and relativism, questions surrounding the function of narrative in history, and the relationship of history to the problems of identity and self-knowledge. The intended upshot of the essay is to suggest that Dewey's brief yet substantial analysis may be capable of supplying the guiding principles for articulating a viable and promising pragmatist (and naturalist) conception of historical knowledge.