Madison, WI
On Capitol Square with the dome filling the windows, built as a tribute to Wisconsin's taverns and supper clubs. The order writes itself: fried cheese curds, a brandy old fashioned (the state's unofficial cocktail and the name over the door), and the bacon-and-fried-egg house burger. Friday brings the fish fry. No reservations on the main floor; the bar holds you until a table opens. Closed Sundays, so make it a Saturday run; brunch starts that morning.
Named for the capital of Wisconsin. Truax Field was a WWII Army Air Forces base; the original 1942 hangars still stand on the field. The Wisconsin Air National Guard 115th Fighter Wing operates F-35A Lightning IIs here, transitioning from F-16C/Ds in 2023 — the first Air Guard unit on the East Coast and Midwest to receive the F-35. Class C, with Madison's State Capitol visible 4 miles south on a clear day.
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.
Before it became the self-proclaimed "Waterpark Capital of the World," the Dells was a genuine natural wonder: a five-mile gorge where the Wisconsin River cut narrow, winding channels through soft Cambrian sandstone, leaving sculpted cliffs, pillars, and slot canyons. A 19th-century landscape photographer named H.H. Bennett made the place famous with his images of the river gorge (and his famous stop-action shot of his son leaping the gap at Stand Rock). The boat tours through the Upper and Lower Dells still show the sandstone formations. Around that natural core has grown a dense cluster of waterparks, go-karts, and Tommy Bartlett-style attractions — but from the air the river gorge is still the bones of the place.
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.
Oshkosh, Wisconsin. Every late July, Wittman Regional becomes the busiest airport in the world. 10,000+ aircraft, 600,000+ visitors, and every type of aircraft from ultralights to B-29s. Even outside of AirVenture, the EAA Aviation Museum is world-class and the grounds retain a hallowed quality for anyone who loves airplanes. If you've never been during the show, put it on your life list. The NOTAM for AirVenture arrivals is legendary in its complexity.