Janesville, WI
On the field at the terminal, named for Bessica Raiche of Beloit, credited as the first American woman to fly solo (1910). Classic 1950s diner inside: vinyl stools, chrome tables, and floor-to-ceiling windows on the runway. Build-your-own destination omelets and seasonal pancakes are the signatures, and the diner features fly-in pilots and their airplanes on its site. Geronimo Hospitality runs it. Open daily 7 am to 2 pm, breakfast and lunch only; time the arrival before the grill closes.
Opened 1942 as Janesville Army Airfield, training P-38 Lightning crews. Postwar civilian, named Southern Wisconsin Regional in 2001. Today an industrial-park GA reliever — flight schools, charter, and the Rock County Veterans Memorial Park preserved on the field. Surrounded by Wisconsin dairy country, with John Deere's Janesville plant 5 miles east.
Frank Lloyd Wright built Taliesin on the hills above the Wisconsin River near Spring Green, in the rugged Driftless Area his mother's family had farmed — country the glaciers missed, all limestone bluffs and deep valleys, which shaped his whole idea of architecture growing out of the land. The 800-acre estate holds buildings from across his entire career and is now a UNESCO World Heritage Site. It also holds the darkest chapter of his life: in 1914, while Wright was in Chicago, a household servant set the house on fire and murdered seven people with an axe as they fled — including Wright's partner Mamah Borthwick and her two children. Wright rebuilt; it burned again by electrical fire in 1925; he rebuilt again. The Taliesin standing today is the third.
Out of Madison (KMSN), ten miles from Taliesin, is one of the strangest places in America. Alex Jordan started building a house on a 60-foot chimney of rock in the 1940s and never stopped. The Infinity Room juts 218 feet straight out over the valley with no supports under the far end, all glass, swaying a little in the wind, and it's plain to see from the air. Inside the sprawl: the world's largest indoor carousel (269 animals, not one of them a horse), self-playing music machines, a 200-foot model sea creature, and room after room of obsessive collecting. A popular story says Jordan built it to spite Frank Lloyd Wright down the road; the place itself says that's false and the two never met.
Milwaukee's downtown lakefront features one of the most photographed buildings in American architecture: Santiago Calatrava's 2001 Milwaukee Art Museum addition, with a 217-foot wingspan brise-soleil that opens and closes twice daily like a giant white bird. Just south is Discovery World, the Hoan Bridge's blue arch, and Lake Michigan stretching to the horizon. North along the shore: Bradford Beach, the Hoan Bridge, the North Point Lighthouse. The harbor, the breakwater, the city's long lakefront park system, and the famed Summerfest grounds all line this same waterfront. The General Mitchell International Airport at the south end is named for Billy Mitchell, the WWI flying ace and prophet of air power who was court-martialed in 1925 and whose hometown was Milwaukee.
Cantigny is just off KDPA in Wheaton; from the air it's a 500-acre estate with formal gardens, and on the south lawn a row of US Army armor sitting in the grass: a Sherman, a Patton, a Bradley, and the guns that worked with them. That armor is the tell for what this place is. Robert McCormick, the Chicago Tribune publisher, led artillery supporting the 1st Infantry Division at the Battle of Cantigny in France in 1918, the first American victory of World War I, and it marked him for life. He named his estate after the battle, hosted Big Red One reunions here for decades, and willed the 500 acres to the people of Illinois. The First Division Museum on the grounds tells the division's story from WWI to now, with recreated environments you walk through: a Western Front trench, the cliffs above Omaha Beach, a Vietnam jungle. Alexander Hamilton commanded the same field artillery regiment during the Revolution; it's one of the oldest in the Army.