Jane Hamilton, A Map of the World (1994) — Set on a dairy farm near Madison in the Lake Geneva area, this novel about an ordinary Wisconsin family in extraordinary crisis captures the landscape, the social fabric, and the moral seriousness of the upper Midwest with unusual precision. It is one of the best novels set in Wisconsin.
Hamlin Garland, A Son of the Middle Border (1917) — Garland grew up in Wisconsin and Iowa in the years after the Civil War and wrote this memoir about farm life on the Great Plains frontier. It's a foundational piece of Midwestern literature and a useful counterweight to the nostalgia that sometimes attaches to rural Wisconsin.
John Muir, The Story of My Boyhood and Youth (1913) — Muir grew up on a Wisconsin farm and attended the University of Wisconsin in Madison in the 1860s, where his earliest inventions (including the alarm clock desk now at the Geology Museum) caught the attention of the faculty. This memoir covers those formative years and helps explain how Wisconsin shaped one of America's great conservationists.
August Derleth, Walden West (1961) — Derleth was Madison's most prolific literary figure, a writer of horror, mystery, and nature writing who corresponded with H.P. Lovecraft. Walden West is his most personal book, a meditation on the Wisconsin landscape around Sauk City just west of Madison, written in the tradition of Thoreau.