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Part I of this Note details the historical moment in which the Law School emerged, sketching both the political and social structure of colonial Connecticut and the multifaceted crisis facing that state’s leaders in the late eighteenth and early nineteenth centuries. Part II describes the response of Litchfield’s elite to this unfolding crisis, focusing in detail on the innovative institutions they founded and nurtured during this period, including the Law School and the Litchfield Female Academy. Part III then attempts to place the Law School in historical and cultural context, providing, sequentially, an exploration of the social vision propounded in its classroom, a brief examination of the school’s legacy, and an overview of other contemporaneous developments in American legal education. In comparing Litchfield with these other early endeavors, Part III also offers some observations on the reasons for Judge Reeve’s relative success.