If you’re in Madison [1], head directly to the State Historical Society Museum [2], whose gift shop bookstore has better holdings than the library.
Lyons, John J., ed. Wisconsin. A Guide to the Badger State. American Guide Series, Works Projects Administration, 1941. From the mother of all guidebook series, the Wisconsin edition, nearly seven decades old, is still the standard for anyone interested in the history, natural history, and culture of the state.
Ostergren, Robert C., and Vale, Thomas R., ed. Wisconsin Land and Life. Madison: University of Wisconsin Press, 1997. This amazing (heavy but eminently readable) book may be the most perfect synthesis of natural history and cultural geography.
Leopold, Aldo. A Sand County Almanac. New York: Oxford University Press, 1949. An absolute must-read for anyone who considers himself or herself to be at all attuned to the land. Also an education for those superficial enough to think central Wisconsin is a vast nothingland.
Olson, Sigurd. Collected Works of Sigurd Olson. Stillwater, MN: 1990. Wisconsin’s seminal ecologist besides Aldo Leopold, Olson had as much influence as his more famous contemporary. This is an excellent overview of his life’s work, writings that show an incredible depth of ecological awareness but are very approachable for a layperson.
McAnn, D. The Wisconsin Story: 150 Years, 150 Stories. Milwaukee: Milwaukee Journal Sentinel, 1998. Most articles are about historical minutiae most folks have never heard about but are fascinating highlights to the general history books. It's engaging and probably your best bet for an easy vacation read.
Nesbit, Robert. Wisconsin: A History. Madison: University of Wisconsin Press, 1989. This is standard reading.
Leary, J. Wisconsin Folklore. Madison: University of Wisconsin Press, 1998. Linguistics, storytelling, music, song, dance, folk crafts, and material traditions. The chapter on Milwaukeeisms is worth the price of the book. Even the Smithsonian has recognized the uniqueness of the book.
Martin, Lawrence. The Physical Geography of Wisconsin. Madison: University of Wisconsin Press, 1965. This is the granddaddy of all Wisconsin geography books, first published in 1916 and updated in subsequent editions.
Reuss, Henry S. On the Trail of the Ice Age. Sheboygan, WI: Ice Age Park and Trail Foundation, 1990. This is a good compendium of the oddball geology of the state and the effort to establish the Ice Age National Scenic Trail.
The state historical society has produced brief booklets profiling every immigrant group in Wisconsin. They’re available from the State Historical Society Museum in Madison.
Bieder, Robert E. Native American Communities in Wisconsin, 1600–1960. Madison: University of Wisconsin Press, 1995. The first and, really, only comprehensive, in-depth look at Native Americans in the state.
Maxwell, R. S. La Follette and the Rise of the Progressives in Wisconsin. Madison: State Historical Society, 1956. This is a fine account of Robert La Follette, the much-beloved Progressive Party politician of the late 1800s and early 1900s.
McBride, G. On Wisconsin Women. Madison: University of Wisconsin Press, 1993. An excellent newer book, this is one of few sources of information about many of the important women in the state’s history.
Meine, C. Aldo Leopold: His Life and Work. Madison: University of Wisconsin Press, 1988. The best book on ecologist Aldo Leopold.
Boudreau, Richard, ed. The Literary Heritage of Wisconsin: An Anthology of Wisconsin Literature from Beginnings to 1925. La Crosse, WI: Juniper Press, 1986. This is a condensed version of the state’s literary canon.
Perry, Michael. Population: 485 (Harper Perennial, 2002), Truck: A Love Story (Harper Perennial, 2006), and Coop (HarperCollins, 2009). Wisconsin has had a few luminaries of literature (Jane Hamilton, Kelly Cherry, Lorrie Moore, et al.), but I think he’s the oughta-be-read author scribbling in the state (my poet laureate). To experience small-town Wisconsin in a wonderfully low-key, hilarious way, read these books.
Stephens, Jim, ed. The Journey Home: The Literature of Wisconsin Through Four Centuries. Madison: North Country Press, 1989. A remarkable multivolume set of Wisconsin literature, tracing back as far as the trickster cycles of Native Americans.
More and more cookbooks detail Midwestern cuisine. Any bookstore worth its salt will have great selections on regional cooking.
Allen, T. and Hachten, Harva. The Flavor of Wisconsin. Madison: State Historical Society of Wisconsin, 2009. A dense volume cataloging all—and this means all—the ethnic groups of the state and their contributions to the cuisine. Terese Allen is one of Wisconsin’s most noted food writers, so look for her name; she updated Harva Hachten’s legendary book.
Apps, Jerry. Breweries of Wisconsin. Madison: University of Wisconsin Press, 2004. This amazing book came out and surprised everyone—a thorough examination of the culture of beer in Wisconsin as had never been done before. It’s not just a guidebook, but a cultural journey. Jerry Apps, too, has written other great Wisconsin books.
Boyer, D. Great Wisconsin Taverns. Black Earth, WI: Trails Book Guides, 2002. The name pretty much says it all. It sounds hokey, but the author is a professional folklorist and storyteller and it shows.
Revolinski, Kevin. Wisconsin’s Best Beer Guide. Holt, MI: Thunder Bay Press, 2010. It’s informative but also fun, from the kind of guy you’d like to have in the shotgun seat on a long trip.
Stuttgen, Joanne Raetz. Café Wisconsin. Madison: Terrace Books, 2004. A folklorist covers the coffeklatsch culture; this is a personal favorite.
Links:
[1] http://www.moon.com/destinations/wisconsin/madison
[2] http://www.moon.com/destinations/wisconsin/madison/sights/downtown-and-isthmus/museum-mile