A few years ago, I couldn’t have pointed to Madison on a map (for those of you still looking, it’s the capitol of Wisconsin). Like the many Americans who populate the coasts, the Midwest to me was flyover country – nothing but a great, grey mass between Seattle and New York.
Vagabondish is reader-supported. When you buy through links on our site, we may earn an affiliate commission. Read our disclosure.
But things have changed, and as chance would have it, Madison has become my home. The city is a bubble in the middle of rural America, a flourishing, liberal urban center squeezed between two gorgeous lakes; outside the limits are miles of dairy farms and cornfields, but you’d never guess it.
Madison is beautiful because of its simplicity – it doesn’t try to be Chicago or Milwaukee, nor does it let itself be pigeonholed as a college town, despite the fact that the University of Wisconsin is half of its beating heart. It is a city with a conscious, with people who are proud of where they live and show their love through supporting local business, local agriculture, and more basically, one another. It has the friendly character of the Midwest without the often-associated kitsch, and a natural beauty that is worth traveling from afar to see.
Madison is at its best in late spring or early fall – come any other time of the year and you’ll be greeted by the extremes of hot and humid or deathly frigid.
Fly into Dane County Regional Airport (MSN) and catch a cab to the Capitol Square. Madison is one of the most bicycle-friendly cities Stateside (up there with Portland, Ore. and Davis, Ca.), so you won’t be needing a car for this trip. Walk around the Wisconsin capitol building, a stunning piece of architectural history and the geographic heart of the city, and take in the offerings of Dane Country Farmers’ Market – the largest producer-only market in the country.
Enjoy a pastry from a local bakery, sample cheese from local dairy farmers, and taste jerky made from local cows, deer and ostrich. Get a loaf of hot, spicy cheese bread from Stella’s to snack on throughout the day and, if it’s fall, a bottle of fresh-pressed apple cider as well.
Have brunch at Marigold Kitchen, one of the best breakfast eateries in town. The daily scramble is always good.
From here, start making your way around the Capitol towards State Street, the thoroughfare that both actually and symbolically connects Wisconsin politics with the state’s flagship university, the University of Wisconsin-Madison. The street is traffic-free (except for buses and taxis) and is lined with local shops and restaurants; the community has fought hard against the slow trickle of nationwide chains onto State Street, but several have inevitably moved in anyway.
Towards the end of State, take a detour to Williamson Bicycle Works and rent either a hybrid bicycle ($15 a day) or a road bike ($30 a day). Wheel yourself towards campus, and then onto the Lakeshore Path, a packed-dirt and concrete route that runs along the edge of the UW campus and the shore of Lake Mendota to Picnic Point, a calm and scenic outcropping into the lake.
Come back to campus, and get yourself a beer and a brat outside the Memorial Union building (It’s a wet campus, and there’s plenty of microbrews on tap. If the employees even ask for it, pull the old “Oh man, I can’t believe I left my union membership card at home!” bit).
Put your feet up on one of the famous Terrace chairs, read a copy of The Capital Times, and soak in the warm sunlight as it glimmers off the lake. Madisonians know how to enjoy the fairer seasons, because they know that -15 degree weather is only so many months away.
Explore the UW-Madison campus. Climb to the top of Bascom Hill, and take in a view of the city from Abe Lincoln’s lap (A statue of the former president sits in front of Bascom Hall, where 600 students staged a takeover to protest the draft in 1966).
After trekking around campus, make your way down to the Chazen Museum of Art and check out one of the various collections on exhibit there (recent showings included Small Arms, a collection depicting child soldiers by photographer Michael Kienitz, and Paper Work, a diverse body of symbol-infused collages created by New York artist Jane Hammond).
Check in at the HI Hostel on Butler Street. The staff is friendly, the facilities are clean and the common room has shelves full of travel guides to help you determine your next destination.
Once you’re settled in, head up King Street (just around the corner) to The Great Dane, a Madison institution and a brewpub that is simultaneously traditional and distinctly Madisonesque – a fusion of Wisconsin’s German heritage and locally refined pub culture. Check the chalkboard for the day’s brews (the Stone of Scone Scotch Ale is always on tap and is phenomenal), watch the brewmasters at work, and have a couple pints while noshing on a fantastic, home-style chicken pot pie out in the beer garden.
It’s been said that Madison has more bars per capita than any other place in the country, the King Street area is home to several of the city’s most vibrant spots – have a whisky and a cigar at Maduro if that’s your thing, or have a glass of Chilean wine and listen to some jazz at Restaurant Magnus. Wherever you go, make sure to end your night at Natt Spil (Norwegian slang for “After Party”). The bar has no sign, so look for a place on lower King emanating red light, heavy beats and the smells of wood-fired pizza. This hip hole-in-the-wall has the best atmosphere in the city, with a dim, all-wood interior and some of area’s most respected DJ’s spinning nightly. Stumble home safely – the hostel is less than a block away.
If you’ve had a proper Wisconsin evening, then you’ll likely still be feeling last night’s beer(s). But worry not, you can shake off that boozy feeling just up the block at Cafe Continental, where they serve the finest (and spiciest) Bloody Mary’s in town, along with several classier takes on french toast and a soulful applewood bacon eggs benedict.
Take your time, digest and nurse any lingering headache with a cup of coffee – life in Madison is best taken at a slower pace. When you feel ready to face the day, hop back on the bike and cruise down to the lakefront. Ride west, and you’ll pass Monona Terrace. The building has become a symbol of downtown Madison, and was designed by Wisconsin’s own Frank Lloyd Wright.
Keep going all the way to Olin Park, where you can take in a sweeping view of downtown. Just across the way is the Wingra Creek bike path, which will take you along a scenic waterway to the entrance of the University of Wisconsin Arboretum, a gorgeous greenspace, and an absolute must-see in fall especially.
If the mood strikes you, take a break from riding at the top of the hill (there’s only one – this is the Midwest) and take a stroll through the trees. Lay on the grass in the shade of leaves and read a book, or just space out at the passing clouds.
You’ll come out of the arboretum a couple miles later at Nakoma – take a right, and you’ll be heading towards the Monroe Street neighborhood. Take a break here at Macha, an old house that has been converted into a teashop, and relax over some tea and snacks.
At the end of Monroe Street, you can hop on a bike path that will take you right to the door of Williamson Bicycle Works – return your bike here, and walk back towards State Street. Have lunch at Himalchuli, a small Nepalese restaurant with wonderful food and lots of vegetarian options.
Walk down East Johnson Street. Head towards James Madison Park and join in tossing a frisbee with some strangers (most people are friendly to this sort of thing), or reflect while looking out at lake Mendota.
Back on Johnson, check out some of the up-and-coming boutiques like drunknButterfly, or grab a coffee at In the Company of Thieves, which is rumored to have obtained many of its cups and silverware by, well, thieving them from other coffee shops.
Stroll several blocks south to the Willy Street neighborhood. This area is known for its distinctly laid-back feel (dare I say, “hippie-ness”), and has plenty of cool shops to check out.
As your time winds down, have dinner at the appropriately-named Weary Traveler. Toss to the wind your concern for the person who will spend their next few hours sitting by you on a cramped airplane, and indulge in Bob’s Bad Breath Burger. It’s cheesy, garlicy, oniony, artery-sticking goodness – everything that makes a quality Wisconsin meal. (Make sure to check out the Weary’s bathrooms, which are plastered with old maps and event posters from around the world.)
Don’t worry about getting to the airport too early; the concourse will be quiet, and passengers will be leisurely sipping a pint of local brew while debating whether to buy cheesehead paraphernalia before getting up to the queue.
On second-thought, do give yourself a bit of extra time – just so you can do the same.