How to Make the Most of a Milwaukee Weekend Getaway


Expressive. Friendly. Industrial. 

Those are three words we came up with to describe Milwaukee, also known as ‘Brew City.’ Why did I take a weekend trip to Milwaukee? Well why not!

Actually, to be honest… if I didn’t live nearby in Chicago,  I don’t know that I would have ever made it up north to visit this nice little city.

Wisconsin is a state I’ve never been to, so after living in Chicago for almost 5 years, I thought it was time to make the short drive to the state border and cross another destination off my list!

I was super excited to getaway a couple weekends ago and explore the breweries, museums and neighborhoods that Milwaukee has to offer. I did little research before leaving, but knew it was going to be a good time! Aside from booking the hotel for our two night stay and getting tickets in advance to see a show that Saturday night, everything else was a toss up. Wingin’ it is the way to go!

If you find yourself not too far from Milwaukee and wondering if it’s worth a short trip, I’m going to say YES. It’s a walkable city that has more than enough to do for a weekend. Here’s how you can make the most of your time spent in Milwaukee:

Stay at the Iron Horse Hotel

The Iron Horse Hotel is an old warehouse turned upscale hotel. The loft style rooms are perfect for a nice little retreat. The decor was industrial and on point. It also offers a fun bar with a pool table in the lobby and a nice, sit down restaurant. Another great aspect of Iron Horse is that they allow dogs, and we got to meet an awesome St. Bernard doggy named Chuck. The staff was extremely pleasant, and the rooms were clean and comfortable. It’s a short walk to a few bars and restaurants, and very close to Purple Door Ice Cream (which unfortunately, I did not get to try because there was always a line out the door). I would definitely stay here again!

Milwaukee Milwaukee

Visit the Art Museum

The Milwaukee Art Museum is one of the biggest museums in America, and has almost 25,000 works of art. Even if you’re not super into art, this is a must-visit. Not only is the architecture of the building that houses the art museum so cool and so well done (I mean it’s a bird with wings – c’mon), but there’s also different exhibits being displayed that can cater to everyone. I was obsessed with the lobby in this place. It’s the perfect spot for pictures, with Lake Michigan being the backdrop. I’m so glad we spent time here!

Milwaukee milwaukee Milwaukee Milwaukee Milwaukee Milwaukee Milwaukee

Take a Brewery Tour

Breweries are plentiful in Milwaukee. From just walking aimlessly around this city, you’re bound to run into some. We managed to visit a few during our stay. Luckily a friend that frequents Milwaukee gave me the tip that Lakefront Brewery does the best tour. I’m not sure what the other ones are like – but this one was fun! AND so cheap! For only $10, you get 4 beer tokens to sample some of their beers, a 45 minute long tour of the factory with a hilarious guide, and a glass souvenir cup at the end. Can’t go wrong there.


Walk Around the Public Market

Stationed in the Historic Third Ward neighborhood of Milwaukee is their indoor public market. You can find all sorts of local food businesses here. It was super busy on Saturday afternoon when we went, but it was still neat to see. Plus, there was free cheese samples. The Historic Third Ward also has all kinds of restaurants and shops, and is totally worth a walk-through.

Milwaukee Milwaukee

Brunch It Up

Like the brewery selection, there were many brunch places to choose from. We decided to do a boozy brunch on Saturday and brunch before the drive back on Sunday. Two brunches in one weekend is my kind of weekend, and Milwaukee does brunch right. The first place we chose was amazing. It was the Smoke Shack, also in the Historic Third Ward. They had a live bluesy singer strumming away on the guitar. We were pleasantly surprised by this. I could have stayed here all day, enjoying his tunes, drinking my jack and chocolate coffee, and eating their giant FREE cinnamon roll. The food was delicious and the ambiance was great for a Saturday boozeday. Milwaukee Milwaukee Milwaukee

See Who’s Playing at Riverside Theatre

Riverside Theatre is a concert hall located in the heart of downtown Milwaukee. It’s an amazing venue to see a live show, and they seem to offer them all the time. We bought tickets to see Umphrey’s McGee, a jam band that was playing in Milwaukee at Riverside three nights in a row. We honestly didn’t know much about them, but figured they must be good in order to hold an audience in the same city for three nights! They put on an awesome performance, and an even better light show.

Milwaukee Milwaukee Milwaukee

Check Out the Harley Davidson Museum

I wouldn’t call myself a ‘biker chick’ by any means, so I was a little hesitant to go to the Harley Davidson Museum during my time in Milwaukee. But, I’m glad I went. This museum is so well laid out, and even offers a couple interactive components: you can build your own dream motorcycle AND you can sit on a few and pretend like your hair’s blowing in the wind. For me, the most fascinating part of the Harley Davidson Museum was learning about how it all came to be and checking out their old marketing campaigns.

Milwaukee Milwaukee Milwaukee

So there you have it folks! A ‘how-to guide’ and itinerary for wonderful Milwaukee. If these ideas don’t keep you busy for a full weekend, then I don’t know what to tell you.

I will definitely be back to visit Milwaukee since it is so close, maybe once the weather gets a little nicer. Or maybe for the infamous Milwaukee Summer Fest.

Milwaukee is an expressive, friendly and industrial little city with awesome vibes and a great dining options. Go see for yourself and let me know what you think!

I'm Abby - a weekend getawayer, lover of beach volleyball, grilled cheese enthusiast and puppy dog admirer.

1 Comment

Leave a Reply

Your email address will not be published. Required fields are marked *