In Madison, Wisconsin’s capital city, with a population of 250,000, you’ll find artsy University of Wisconsin–Madison co-eds cramming at fair-trade coffee shops, hardy bike commuters zipping to software industry jobs and a rotating schedule of farmers’ markets, craft beer festivals and live music. Midwinter, even freezing temps don’t send everyone running indoors: When the city’s five surrounding lakes freeze over, they become playgrounds for ice hockey, snowshoeing, cross-country skiing and a niche sport called ice sailing.
To do it right, you need conditions to align—thick ice, strong winds and not too much snow, which happens about a half dozen times each winter. When it does, locals flock to Lakes Mendota, Monona, Kegonsa and Waubesa on boats equipped with sails and three skate-like runners fixed to the hull. The boats whip along the ice at speeds over 40 miles per hour. Ice sailing came to Madison sometime in the mid-1800s as a way to haul construction materials; today you’ll find weekend races that draw in hordes of spectators.
Nobody rents ice boats or teaches lessons—it’s not exactly an entry-level sport—but don’t let that deter you. To join the action, reach out to the Four Lakes Ice Yacht Club and ask to join a crew in the next regatta. “These boats can travel four times the speed of wind,” says Deb Whitehorse, the club’s secretary. “When the wind takes hold, you’re just a few inches from the ice. It’s the closest feeling to flying you can get.”
Take a stroll
Start at Capitol Square and walk down State Street to the University of Wisconsin–Madison campus. The street is closed to cars and is filled with street musicians, food trucks and cyclists. You can shop for handmade hats or vintage toys and dine on everything from Nepalese dumplings and Cornish pastries to Wisconsin brats.
Listen: A warm yet electrifying playlist
Need a break from the cold? Visit Bolz Conservatory at the Olbrich Botanical Gardens midwinter and you’ll be treated to a tropical jungle with 80-degree temperatures inside a 50-foot-tall glass pyramid filled with tropical birds, a rushing waterfall, rare orchids and carnivorous plants. Admission is free on Wednesday and Saturday mornings.
You can watch ice-boat races over brunch from your Lake Monona waterfront table at Sardine, which serves up cherry buckwheat waffles and braised pork and fried egg sandwiches. Or dig into a seasonally inspired farm-to-fork dinner at Field Table, which opened last spring as a restaurant that doubles as a market and coffee shop.
A historic Madison location since 1948, the Edgewater Hotel (from $399) underwent a major renovation in 2014. You’ll get well-appointed rooms with views of Lake Mendota in a central downtown location. Or stay at the new AC Hotel Madison, opening this winter at the old site of a beloved tire company a block from Capitol Square. For a relaxed option, the Hotel Ruby Marie, the city’s oldest hotel, is a charming Victorian-style bed and breakfast with a complimentary happy hour.
Stay out late
It’s not just frat guys and Ph.D.s drinking brews at Der Rathskeller, a German beer hall in the university’s student union. The entire city comes here to clink pints, eat cheese curds and watch Packers games. For a swankier bar, head to Graze in Capitol Square for local ales and craft cocktails, such as an Old Fashioned made with maple syrup, cherry vanilla bitters and rye aged 10 years. And although it might sound strange to visit a southern joint in the far north, locals love the margaritas at Eldorado, which has Madison’s largest tequila inventory.