Chances are you know a few things about Madison. It’s a big-time college town about three hours from Chicago, and it’s in Wisconsin, so there’s lots of beer and cheese, right? Right, but this vibrant Midwestern city is also so much more, with a wealth of lakefront dining—on not one but two lakes—and outdoor recreation opportunities out the wazoo.
Arriving in Wisconsin’s capital, you might first be struck by the number of bicycles—bike shops dot most neighborhood corners and dozens of BCycle (madison.bcycle.com) stations offer easy access if you’re in town without your own two wheels ($3 for 30 minutes or $6 a day). You’ll see couples out rollerblading, people jogging and twentysomethings on skateboards. The thing is, you really don’t need a car to explore this city of 250,000. Madison is so bike-friendly that hotels like the lakefront Hilton Madison Monona Terrace (9 E Wilson St; 608-255-5100) have bike elevators and many businesses across town offer special discounts for cyclists (bb2.bicyclebenefits.org).
But it’s not all go, go, go. If you want to spend the day in the grass, in a kayak or on a restaurant patio, you can. Make it more relaxing with a beer, like local favorite farmhouse ale New Glarus Spotted Cow, while dining at downtown Madison’s only rooftop restaurant, Fresco (227 State St; 608-663-7374, frescomadison.com) or sitting outside at Wisconsin Brewing Co. Tap Haus (107 State St; 608-310-1010, wisconsinbrewingtaphaus.com), and people-watching. For a serious dive near the capitol, Paradise Lounge (119 W Main St; 608-256-2263, thenewparadiselounge.com) has every regional offering you want on tap, from Pabst to Ale Asylum, while offering up bacon cheeseburgers and brats to a soundtrack of bands like Slayer. Whatever you do, make time for a stop at the Old Fashioned (23 N Pinckney St; 608-310-4545, theoldfashioned.com) for cheese curds and, well, any of the variations on an old-fashioned, of course.
For a quick bite, grab pizza from Ian’s (100 State St; 608-257-9248, ianspizza.com), open until 3am on Fridays and Saturdays. While Madison is most definitely a city of great eats across price points, you can also find plenty of quirky shops to walk off all that snacking and drinking and take home a few souvenirs, whether you want to browse books at A Room of One’s Own (315 W Gorham St; 608-257-7888, roomofonesown.com) or fine cheeses from Fromagination (12 S Carroll St; 608-255-2430, fromagination.com). Mark your calendars for one of the U.S.’s best farmers’ markets (Saturdays), and don’t miss one of summer’s biggest events, the Isthmus Paddle & Portage (paddleandportage.com) canoe race, on July 30.
On your way out of town, don’t miss hip Near Eastside neighborhoods like Atwood and Marquette. Vegetarians will want to grab brunch outside at Green Owl Café (1970 Atwood Ave; 608-285-5290, greenowlcafe.com), and everyone can appreciate hand-crafted chocolates from Gail Ambrosius (2086 Atwood Ave; 608-249-3500, gailambrosius.com). Driving? It’s worth venturing to nearby attractions like New Glarus Brewing Company (2400 WI-69, New Glarus, WI; 608-527-5850, newglarusbrewing.com) and House on the Rock (5754 State Road 23, Spring Green, WI; 608-935-3639, thehouseontherock.com). The latter is a Frank Lloyd Wright–inspired funhouse, complete with optical illusions and a massive indoor carousel. Perhaps like everything in and around Madison, it’s full of weird but pleasant surprises.