Planning a 3-Day Weekend in Madison, WI

Moving to the Midwest has been such an awesome life change – an opportunity to slow down, focus on my finances (because, you know, I work too much to not have any money), and just… right-size life expectations. So refreshing.

In my nearly 2 years here, I’ve learned that people have their own lives too and aren’t going to be able to just stop what they’re doing and visit me so, when they do, it better be special! My sister’s been the only one to visit so far and she did so in my first year here in the Fall hoping to get a fun-Fall weekend apple picking, cider, leaves changing color… but, instead, poor thing got rain, a hospital visit because I hurt my lower back, took care of me and then took an Uber back to Milwaukee to fly out (yes, it can be pricey to fly into Madison).

So when my sis and her new fiance (!) decided to come visit this year, in late April (Easter weekend), I knew I had to show them the gem that is downtown Madison.


I live on the West side and while I could have had them stay in a hotel on the West side, I thought it best for them to try to get an AirBnB on the square/around the Capitol building. I found this precious home right on State St – the main thoroughfare of downtown Madison that runs from the Capitol building to the UW campus. It has a great cafe right downstairs, and a beautiful bay window looking over State St. 

My sister and brother-in-law flew in on a Friday from San Diego and I picked them up around 11am (wooo I had a 4-day weekend for Easter!). Below is a quick overview of the go-to places and things we did during their 3-day weekend visiting in Madison!

Knowing they had a 2 hour time difference, and that they flew overnight, they wouldn’t want to sleep or rest right away so I planned a full day.


  • Lucille for brunch – in hindsight, a little heavy, but a perfect and easy lunch/brunch option because… pizza.
  • They had to check-in to their AirBnB at 3pm so we walked State St (quiet-er than a Saturday) and stopped in some bars here and there for a beer/snack along the way; highly recommend Hawk’s for a quick beer – love checking out their “wall of fame”.
  • My beau and I left them around 3-4, went back to the West side to relax for a few and then joined them back downtown for a 6:30pm reservation at Eno Vino – must do. Was beautiful to watch the sunset followed by the Capitol building lighting up into the most clear evening; not a cloud in the sky. Amazing tapas options on the menus and over 100 wines to pair – don’t miss out the view from the women’s bathroom and the outdoor patio too… pretty beautiful.


  • After dinner, we bar-hopped a bit. My brother-in-law was interested in seeing a basketball game and we were pleasantly surprised by Paul’s Club on State St. I thought it’d be a dark, dingy pub but it’s actually very open with spot-on mood lighting and pretty decor on the ceiling.


Saturday morning was very obviously held for Madison’s Saturday morning farmers market around the square, Saturday on the Square.

  • Make sure to grab a coffee from Collectivo and start at that corner of the market
  • Work your way around and don’t forget to stop for a loaf of Stella’s Cheese Bread… it is… amazing, must have. You can just pick at it while you slowly (not too slowly) follow the hoards of people around the square around the Capitol building – can be overwhelming but a sweet time. Try the cheeses, the hot sauces, the fresh veggies, the honey, all the fresh things.
  • From the square/farmers market, hop into the Capitol building to cool off and look up at the beauty of the inside of the building. Also quick tidbit: if you need to get across the square… cutting through the Capitol is faster! All 4 sides have entrances you can cut through if you want/need to get somewhere quick.
  • From the square/farmers market, you can also hop back onto State St and head all the way down to explore the UW campus ending with a beautiful lake-front view and beer at the Terrace at Memorial Union. Beautiful, relaxing break in the day.


  • We left downtown Madison for our brunch and evening – headed to the Hilldale Mall, which I recommend walking for an early morning followed by brunch if you have time. It’s a great little mall just outside of downtown with some great stores and restaurants. Specifically, Cafe Hollander – truly yummy from drinks to apps to entrees.


Sunday was a short day for us as my sister had to be at the airport by 2:45ish. Since it was also Easter, we were limited by restaurants and things to do that were open but we decided to stumble into DLUX  back downtown/on Capitol square. DLUX has a small but delicious menu, and they stay on top of the mimosa refills if you get unlimited mimosas from the menu.

We also grabbed a last beer at the Great Dane Pub & Brewing since the other breweries in town were closed; additionally, they have pool tables and shuffleboard- very chill, relaxed bar to hang or grab lunch at.


So it likely sounds like ALL there is to do in Madison is eat and drink beer… those definitely are the top two things to do … and my gosh, I didn’t even touch on the longer list of amazing restaurants to try like Sardine, The Old Fashioned, Graze, Harvest, just to name a few. But here are some other ideas if you’re in a crunch for more activity on your weekend in Madison:

  • The Olbrich Botanical Gardens (beautiful)
  • Proper tour of the Capitol building
  • UW Madison Arboretum
  • Monona Terrace (overlooking Lake Monona)
  • Take a walk/hike/bike on one of the many trails in Madison
  • Any of the awesome museums downtown
  • Grab a drink and craft at Revel
  • Check out any local brewery
  • I’m also a huge fan of downloading the Facebook Local app – great way to know of pop-up/last-minute events, farmers markets, etc.

Hope you enjoy your weekend in Madison!

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