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From the vantage of the twenty-first century, it seems remarkable that farmers, working with only hand tools and farm animals, converted over half of New England’s “primeval” forests to tillage and pasture in the eighteenth and nineteenth centuries. This period was marked by transitions as farmers responded to new markets, changing family values, and declining natural resources. These forces brought an end to agrarian expansion and caused New England’s iconic pastoral landscape to begin to revert to forestland. A case study based on the former Jabez Besse, Jr. farm in central upland Maine provides a link to New England’s agricultural landscape history and the practices and values of families whose lives were focused on the improved acre. Theresa Kerchner earned a Masters Degree in Ecology and Environmental Science from the University of Maine in 2002 where she researched the land-use history of the Besse farm in Wayne. From 1997-2003 she worked with local classes and community members on several studies in natural history, local history, and art, and co-edited Life and Schools in Wayne, 1890-1940; Waiting: An Anthology of Poems and Photographs of a Year with Hay; Images of Our Community; and Our Year with Birds: Local Lessons in Ornithology, Ecology and History. She is currently the Stewardship Director for the Kennebec Land Trust in Winthrop.