Minneapolis, Minnesota, To Madison, Wisconsin

The Bachelor Farmer in Minneapolis

ROUTE: Fly into MSP Airport, enjoy the city's chic restaurant circuit, then head east, taking the back roads through Mississippi River farm towns to Madison.

Dive in at the World Street Kitchen food truck for a post-flight curry-chicken bánh mì, walleye tacos at The Tin Fish, and a croque-monsieur with locally raised ham at Barbette. Spend happy hour at Eat Street Social sipping egg creams with Minnesota maple syrup before dining at Nordic-cool seafood joint The Bachelor Farmer.
Crash here: Le Meridien Chambers, a mash-up of contemporary art and landmark architecture.

Fuel up at Wise Acre Eatery with a Half-Caff-N-Fully-Fultonated (espresso and local IPA), then head to Red Wing, Minnesota—home of the heritage workwear brand and also chocolate-covered pretzel sticks from Red Wing Confectionery—before veering to Stockholm, Wisconsin. Hit Stockholm General for regional specialties like Bolzano salami, then continue east to Pepin's Harbor View Café, gearing up for the four-hour trek to Madison with braised lamb and peach crostada.
Crash here: HotelRed, a hip inn within shouting distance of the university's stadium.

Start off at Bradbury's Coffee with a flat-white and a savory crêpe, saving room for a brunch of gourmet fried cheese curds at Graze. The college town is bordered by two lakes, so pick up picnic eats—Black Sheep Truffle cheese from Carr Valley and Washington Island Flax crackers from Potter's—at Fromagination to tide you over until a decadent dinner at L'Etoile, where the James Beard Award-winning chef celebrates the state's bounty with dishes like an escargot tarte flambée with Wisconsin Cheddar.
Crash here: The American Club, a resort and spa with views of Lake Michigan.