Woodstock, Cedarburg & Madison: Three Landmark Downtowns

Three days from Illinois to Wisconsin through two underrated historic districts and one university city. Woodstock's Victorian town square is where Groundhog Day was filmed — 30 weeks on location in 1992, still fully intact. Cedarburg on day 2 is a National Historic District: the Cedar Creek Grist Mill has operated continuously since 1855, Washington Street's limestone commercial buildings house genuine art galleries and wine rooms, and the Sybaris Pool Suites in Mequon are the best romantic overnight on Milwaukee's North Shore. Madison closes the trip with the Wisconsin State Capitol — its dome is taller than the US Capitol — plus State Street, the Chazen Museum of Art, and The Old Fashioned for a proper Wisconsin supper before the 2h 15m drive home.