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This essay follows the footsteps of a rather unknown author, Moshe Kerner (1762–1836), an itinerant preacher who traveled throughout European Jewish communities from the northern Pale of Settlement to Amsterdam. In the books Kerner published along his endless journeys, he offers a unique historical perspective on European Jewry approaching the modern era. He reflects its broader social and cultural contexts, including the appearance of modern ideological and religious movements. Kerner's life story is presented here as ideologically complex within contemporaneous Jewish culture, since he emerges as an intermediate figure who took a step in the direction of the new world but ultimately withdrew from it towards a conservative worldview. His contested cultural perspective undermines some historiographic tendencies towards "modernity" and calls for its reconsideration.