I spend a lot of time trying to convince people in Chicago that Madison, Wisconsin is one of the coolest cities in the country. I get a lot of blank stares or condescending smiles. But if you’ve been there, you know.
We’ve been visiting a couple of times a year for the past few years and have fallen in love with Madison. It is the state capitol of Wisconsin and also home of the University of Wisconsin, which makes it very much a college town. It is a progressive city, sometimes referred to as the Berkeley of the Midwest. It is built on an isthmus and surrounded by four (five?) beautiful lakes. Nature and urban life flow together in wonderful ways in Madison. It has a thriving food scene and is one of the friendliest places you’ll ever go. Because it is in Wisconsin, beer and cheese are plentiful. Basically, it is paradise.
I thought it was time I shared my favorite places with you. This is not intended to be a comprehensive guide to Madison, I’m not an expert. This is just a listing of the places we like to visit when we are there. I hope it might be useful when you’re planning your trip. I’ll try to keep it updated as we try new things, and I am sure people will have their own suggestions in the comments. I really hope it inspires some of you (especially my fellow Midwesterners) to plan a visit.
FOOD + DRINK:
Since Forequarter opened, we’ve never been in town without eating here. I consider it among my favorite restaurants in the world. I know that sounds like a bold claim, but it is true. Restaurants are complex sites that need to bring together good energy, good food, and good people. If it happens right, magic is produced. Forequarter is the ultimate neighborhood restaurant, but they make out-of-towners feel like regulars. The food highlights the best of Wisconsin and the Midwest and is outrageously good. Last year there was a dish of coffee-roasted beets with buttermilk ice cream that blew our minds. I’m always learning about a new technique or ingredient when I eat here. I’m also a big fan of their bar. A recent menu featured a cocktail called Great Plains which brought together a burning corn husk, squash juice, and mezcal into something truly exceptional. Forequarter is mandatory. Forequarter is magic.
Underground Butcher and Forequarter are both products of Underground Food Collective  (UFC), a collaborative group that promotes sustainable Midwest food and community. As a butcher shop, Underground Butcher is a dream. The butchers are all friendly and charming (and cute) and enthusiastic and knowledgeable about the animals they sell. The shop also sells UFC’s own outstanding line of charcuterie, under the label of Underground Meats. But the shop is so much more than meat. They also sell a line of housemade preserves and pickles, bakery (including some really delicious cookies and crackers), as well as dairy, alcohol and other pantry items from trusted suppliers. It is the perfect food shop. We stop here on the way home and load up a cooler with delicious food.
Layla’s is unlike any other restaurant. It is a tiny space, tucked away in the basement of a youth hostel. There is one employee, Leila Borokhim, who takes your order, cooks your food, clears your table, and jokes around with you in between. People looking for a quick lunch should maybe go someplace else. People who lack a sense of humor, and patience, should go someplace else. But the food, oh, the food. This is truly some of the most delicious Persian food I have ever eaten. And the baklava, one of the few sweets I don’t usually care about, is revelatory. I’m obsessed.
One of my favorite pizzas anywhere, ever. Seriously. The original is in an unassuming strip mall in Sun Prairie, about a 20 minute drive from Madison (and worth every mile), though they now also have a location down the street from Forequarter on Johnson. East coast style pizza, but with sauce on top. I recommend getting one with calabrian chile peppers. Their standard garden salad is like a farmers market come to life: edible flowers, sugar snap peas, multiple varieties of radishes, beets, carrots, onions, cherry tomatoes. It’s insane. I highly recommend ordering enough pizza so you can take some home. You’ll be so sad otherwise.
You can’t be a good city without good bread. Madison Sourdough provides it for Madison, along with delicious baked goods and lunches. A few months ago they opened a french patisserie next door and it is perfect. Classic French pastries that are extremely well executed. Their sable Breton is especially memorable.
Old school Madison steakhouse that is COOL. It’s expensive for dinner, and there are better options, so go after 10pm for their late-night menu and drinks. Sit in a curved booth and order some cheese curds and a couple of beers and you’re ready for a fun night.
Craft Cocktails on Willy Street. Solid cocktails in slick new space (inside an old house). They have a few snacks on the menu, but really you’re coming here for a nice cocktail before or after dinner.
Impressive pan-Asian food from one of Madison’s most famous chefs, Tory Miller (see L’Etoile/Graze). What the newly constructed space lacks in character, is more than made up for with the food.
Tip Top Tavern 
Nothing fancy, but a really solid neighborhood spot in a former dive bar. The space has been beautifully renovated and the food is good.
Natt Spil 
I’ll be honest, I don’t love the food or drinks here, but I love the atmosphere so much that I am including it. It is cozy, and the perfect place to drink a beer on a snowy night. Get a beer and the Middle-eastern plate.
Osteria Papavero 
Locally sourced Italian food. Great charcuterie program. The Nduja pasta is wonderful.
During the summer, it can feel like the entire population of Madison is here drinking beer and listening to music. It is the place to hang out in Madison during warm weather. I could (and have) spent hours here enjoying the glory of a Midwestern summer.
Coffee shop that sells crepes right off of the square. Really lovely place to start the day or get a snack.
Willy Street Co-op 
Great coop, though its recent remodel has left if feeling a little less like the hippie den it once was. I love visiting grocery stores on vacation and this location is a major part of the Willy (Williamson) Street community.
Fantastic cheese shop with a stupid name. Spend some time here talking with the cheesemongers (many of whom are studying cheese-making at the university) and sampling Wisconsin’s finest cheeses. I love anything Willi Lerner (Bleu Mont Farm) produces, and his bandaged cheddar is an all-time favorite. Wisconsin cheeses are the best. Truly.
Greenbush Bakery 
Madison’s favorite donuts. They’re good, like donuts are.
L’Etoile is the OG fancy Madison foodie destination. It’s great, and chef Tory Miller is a genius with local produce. My only real complaint is that it feels a little stuffy and it is expensive. Still, worth doing at least once. Graze is it’s casual cousin next door, and has my favorite cheese curds in town.
I’m surprised by just how good this ice cream is, it has a real pure dairy flavor (which I guess shouldn’t be a surprise in Wisconsin?). I am a fan of the blueberry cheesecake, which has pieces of cheesecake folded into the ice cream. Don’t blame me when you have a heart attack.
Great coffee and quintessential coffee shop vibes.
The best farmers market in the country, and I will argue with you if you tell me otherwise. The variety and quantity of things available is spectacular. But most importantly, it is affordable. Every time I shop here I am reminded of how silliness and inaccessibility of Green City Market in Chicago. The market surrounds the capitol building and as you will quickly discover, everyone walks counterclockwise around the square. I recommend making two full loops, one to scout out your options, and the other to make purchases. Look out for hickory nuts, a rare treat. No visit to the market is complete without a stop at Stella’s Bakery for their famous hot and spicy cheese bread.
Burnie’s Rock Shop – Quirky rock shop, great fun.
Context Clothing – Men’s clothing store that carries labels you expect to find in bigger cities and will be impressed to find in Madison. A bunch of friendly guys work here. Prices are high, but the quality is good.
The Kitchen Gallery – Fantastic kitchen store. They have everything as well as a good selection of cookbooks.
A Room of One’s Own – Feminist/progressive book store. Pretty good cookbook selection.
THINGS TO DO:
Geology Museum 
This museum could be in a museum and I love it for that. Bryan says it combines his love of natural history and my love of pretty sparkly things. True.
Picnic Point 
Nice place for a walk on the university campus. Great views of the capitol.
Impressive gardens, and a nice place to spend an afternoon. You could bring a picnic from Underground Butcher and sit at the lakefront.
Chazen Art Museum 
Decent collection, and some good special exhibitions. Great views of the lake from the second floor galleries.
Small contemporary art space that hosts traveling shows and exhibits by local artists.
UW Arboretum 
A great place for a hike.
Getting there: Madison is about a 2.5 hour drive (sometimes less) northwest of Chicago.
Where to stay: I’m not sure it matters. We’ve stayed at many different hotels and they were all fine. We splurged on a recent trip and stayed at the newly renovated Edgewater Hotel, and it was a disappointment. It is sort of fake-fancy and the design felt soulless/corporate, which you can find elsewhere for half the price. I’d rather save the money to spend on cheese and beer. The Hampton Inn  is a solid, reasonably-priced choice. The Hyatt Place  is also a good choice. Generally speaking, I like staying near capitol square because it makes it easy to walk to many things you’ll want to do, and to stumble home drunk on cheese curds and beer. Bottom line: You don’t really go to Madison for the hotels, so just get a good deal at someplace comfortable.
Timing: Because the farmers market is Saturday morning, I think it is best to arrive in Madison on a Thursday or Friday and head back to Chicago with a car full of fresh food on Saturday. Because of all of the delicious food to eat, I think a two night stay is ideal, though one night will do in a pinch. If you’re visiting in the autumn, I would check the football schedule to see if there is a home game. It makes a difference. You may or may not like the difference.
When to go: I’ve been to Madison in every season and I think they’re all great. October is probably my favorite month to visit, but summer is wonderful and less busy because school and the legislature are out of session. I’ve also gone mid-winter and had fun, though it can get cold.
Wisconsin cocktails are sweet. Too sweet for me, even at nice restaurants. The only exceptions I have found are at Forequarter and Gibs. But mostly, stick with beer. Even at the lamest tourist restaurant you will be able to get a delicious pint of locally brewed beer, and it will be cheap. Delicious cheap beer is a core Wisconsin value. #bless
Eat fried cheese curds. As many as you can, as often as you can.
Stop at a Woodman’s  to see what seems like the largest grocery store in the world, that happens to be employee owned. They sell New Glarus beer , the coveted only-in-Wisconsin brew that Illinoisans bring back to friends.
Finally: Wisconsin is a pretty conservative state, though you wouldn’t know it in Madison. In 2011 Governor Scott Walker (a legit monster) and the Republican legislature’s anti-union agenda prompted some serious, and impressive, resistance by people in Madison, and throughout the state. Ever since the Wisconsin Uprising  (as it has been called), a Solidarity Sing Along  has taken place in or around the capitol building. It takes place every day at noon and anyone can join. Protest songs are sung, and camaraderie is fostered. It’s a really beautiful thing that makes me happy to be a human and so proud of everyone who participates.
Grill some brats, tap a keg
And pass the cheddar
We’ll be here ‘til Wisconsin gets better