Why should we visit your town/city?

Have you ever spent a weekend in a big city and felt drained afterward (mentally or financially)? Have you ever visited a small city and run out of things to do there? With a little over a quarter million people, nestled between two gorgeous lakes in south central Wisconsin, Madison hits a cultural and practical sweet spot of American travel. It’s just-big-enough size ensures that you’ll have a ton to do without spending half of your stay trying to figure out a metro system or half your budget on parking or Ubers. Because it’s home to the state university’s flagship campus as well as the state capitol, Madison strikes a delicate balance between fun and finery. It’s got a vibrant music scene, top-notch craft beer offerings, some phenomenal food, and did I mention its stunning lakes? Sure, Beyoncé will probably never perform there, but The Avett Brothers are there on the regular. So if that’s your speed, Madison might be a good choice for your next weekend away.

I won’t lie to you and suggest that Madison is just as fun in the winter as in the summer. Maybe it’s my Virginia roots, but even after living there for six years, I still think Madison winters are brutal. The summers, on the other hand, are idyllic. (Occasionally, I meet a Madisonian who complains that it’s too humid and hot in the summer there, but they’ve clearly never spent a summer day in D.C.!)

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Where should we stay?

Full disclosure, I’ve never stayed in a hotel in Madison. But I lived there for six years, so I can gladly give you a few pointers. Madison is built on an isthmus between two lakes, and right at the very heart of it sits the state’s capitol building. They say all roads lead to Rome, but in Madison, all bus routes lead to Capitol Square, so staying near it puts you in the best position to get anywhere else. It’s also where most of Madison’s free events take place.

If you’re feeling bougie, spring for the Edgewater, which as the name suggests is right on the water, and has a lakeside restaurant serving up a view of the sunset over Lake Mendota. There’s also a spa (that maybe one day I’ll be able to afford). Another upscale option would be the Madison Concourse Hotel, just around the corner from State Street, where a lot of the fun happens in Madison.

If you’re traveling on a budget, no problem. There are some solid, affordable options in the city center. The Hilton Madison has some affordable rooms and is right next to the Monona Terrace, a public event center with a rooftop garden offering both a cafe and an absolutely breathtaking view of Lake Monona. Another option is the Hyatt Place Madison Downtown, which is close to State Street and right across the street from Madison’s best sushi spot (more about that in a minute).

Where should we eat?

If you’re looking for a real Wisconsin experience, The Old Fashioned is a common recommendation—and there’s good reason for that. You’ll find a great local beer selection, a solid selection of burgers and sandwiches, and other Midwestern staples like cheese curds and bratwurst, all made with ingredients sourced in-state. Don’t forget to try a hand-muddled Old Fashioned, of course. Other solid options would be Tipsy Cow (I think it’s the best burger in Madison!), or Dotty Dumpling’s Dowry.

We always brought our visitors to The Old Fashioned, but on a typical weekend in Madison, you could find me grabbing some sushi with friends at Red, which offers reasonably priced Japanese fare in a sleek spot. Share some edamame to start—the Gochujang sauce is *chefs kiss*. Another favorite in my family is Naples 15, which serves up authentic Neapolitan pizza with a great selection of Italian wines. The staff there will always hold a sweet spot in my heart for how lavishly welcoming they were when we brought our two young daughters in for my husband’s birthday dinner. They even gave us a little complimentary Prosecco to wash down all the pizza.

For date nights, try tapas at the Eno Vino Downtown. The food is great, and the views from the rooftop bar are unbeatable. For special occasions, my husband and I would get the Chef’s Tasting Menu at Estrellon, and any of Chef Tory Miller’s restaurants would be a good upscale choice.

Don’t think I forgot about breakfast. Marigold Kitchen is the go-to spot for a chatty brunch with my girlfriends. It’s a bustling spot on weekend mornings (the line very often extends out the door, but it moves fast), so it might take a minute to find a table, but it’s worth it for the duck confit hash. That said, I think the best eggs benedict I’ve ever had in Madison was at Heritage Tavern, a bit of a fancier option. If you’re looking for a quick breakfast, grab some coffee and crepes at Bradbury’s, a breakfast sandwich at Johnson Public House (where they serve breakfast all day), or a bagel sandwich at Gotham Bagels (best bagels in Madison, hands down).

Which coffeehouses are the best and why (for coffee, for atmosphere, for both)?

Alright, we’re getting into controversial territory. The truth is there are a ton of trendy little coffee shops scattered all over downtown Madison, and no bad options. Crescendo, in the Monroe street area, makes a solid latte and has live music on Fridays. Lakeside Cafe offers a quieter, low-key setting with a view of the Monona Bay. But the place I’ve spent the most time sipping lattes over a book, studying, or chatting with friends during a book club meeting is Colectivo (either the Capitol Square or Monroe street locations), a regional chain with locations in Chicago, Milwaukee, and Madison. They’ve got some great cold brew and mouth-watering pastries, and when the weather is nice they open up the windows in the front room, allowing a refreshing breeze to flow through the entire building. When I go back to visit Madison, this is where I’ll grab coffee before the farmer’s market.

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What sites should we see?

The key to a great weekend in Madison is to enjoy the lakes, and there are plenty of ways to do that. Take a hike out to picnic point. Rent some kayaks from Olbrich Park or Brittingham Boats. If you want a real adventure, rent a bike from Machinery Row, and do the lake loop, a 13 mile bike path around the Monona. Or simply take in a view of both lakes from the top of the capitol building, which has a 360 degree observation deck.

Another cherished lakeside pastime is to share a snack or a pitcher of beer with friends at a location by the water. For this, any guide to Madison will point you in the direction of the Memorial Union Terrace, where you can go for a dip, watch live music, or just sit in one of the terrace’s famous colored chairs and enjoy the view. (You will need a guest day pass to buy food or beer at the terrace, but it’s free. Just let them know you need one when you order.) Try some Babcock ice cream while you are there.

If you are looking for a more toddler-friendly or quieter option, I’d suggest heading across the isthmus to The Biergarten at Olbrich Park. It’s a no-frills spot in a public park serving a rotating selection of local beers and some snacks (think soft pretzels), with an absolutely jaw-dropping view of the state capitol over the lake. It’s my favorite spot to watch the sunset in Madison. Bringing food in from outside is allowed and encouraged, so bring a picnic! Pro tip: this is a counterintuitively good choice on hot days, because there’s plenty of shade and a steady breeze coming off the lake.

Madison has a lot of events during the summer, many of which are free, so be sure to check out the event calendar ahead of time to see what’s happening. Enjoy some music at Live on King Street, an annual free outdoor concert series held on Friday evenings. Eat your way through the city at Taste of Madison, a Labor Day weekend event where restaurants around Madison showcase their food. Scope out a massive selection of national and local art at Art Fair on the Square. Go shopping during Maxwell Street Days, an annual sidewalk sale on State Street that always takes place on the third weekend of July. If you’re visiting on a Wednesday during June or July, bring a blanket and bottle of wine to Concerts on the Square, a free concert series on the capitol lawn put on by the Madison Chamber Orchestra. And don’t forget the Dane County Farmers’ Market, a massive farmers’ market on Capitol Square every single Saturday morning from Mid-April to November—try an empanada and maybe some spicy cheese bread from Stella’s while you’re there!

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Editor’s Note: Due to COVID-19, some of the event and location suggestions in this article may not be available or open in summer 2020. Be sure to check before you travel!