Explore Milwaukee this Fall: A Weekend Guide for Visitors

Explore Milwaukee this Fall: A Weekend Guide for Visitors

Sneaking away for the weekend to Midwest cities has been my new way of life. Each town and visit feels familiar but is also distinct.

I recently went on a fall trip to Milwaukee from Chicago. I had a meeting this week with the Germany Travel Tourism Board. While I can’t make it overseas right now, I did the next best thing and went to Milwaukee – a city that started growing with an influx of German immigrants in the 1840s and 1850s.

I went to celebrate my friend, who just bought a condo in her 20s. (Woah!) She chose Milwaukee, a place where she knew no one and never lived. It was a place much more affordable than Chicago to buy a condo, but still offers a city life. Intrigued, I went to experience this land of beer and cheese curds.

I’ve been to Milwaukee a few times – usually passing through for a drink or two as we made our way to a Wisconsin lake house. I wanted to share some of the highlights with you – not to convince you to move – but as an affordable option to get out of the city for a day or weekend.

Getting to Milwaukee from Chicago:

The easiest option and the most comfortable is to take the Amtrak to the Milwaukee Intermodal station. It’s $50 round trip and leaves you in downtown Milwaukee. I was only a 15 minute walk to my friends condo when Amtrak dropped me off.

Another option is to take the a Greyhound bus. It drops you off at the same station and a one-way ticket is as low as $10! That’s literally less than some of my Uber rides.

Milwaukee Attractions:

Milwaukee is a very walkable city. In fact, my friend doesn’t even have a car and just talks everywhere. She is in the Historic Third Ward, which is right by the river and Milwaukee Public Market as well as bars and pubs. I liked how beautiful and peaceful it was, but also full of things to do.

Sweet Diner:

I started off my trip freezing – because it is the Midwest. So, it went from upper 60s to mid 30s. No one was prepared. I went to Old Navy and impulse bought a coat and jeans because I couldn’t feel my knees in my dress. I seriously don’t even know why I packed. Vacay feels better when you get new clothes anyways 💁🏻‍♀️

We spent Friday night in having cupcakes and vodka cranberries. So, Saturday morning we were ready to really explore and we started and a gorgeous cafè, Sweet Diner. I felt like I was in a cozy Restoration Hardware. It has beautiful, bright white walls, exposed brick, and a striking gold chandelier in the center.

Even though I passed by a bucket of champagne, I opted for the green juice. Because you know – cleanse before the cheese. My friend and I decided to split the Milwaukee omelette- which had cheese curds in it- and the chicken and waffles. It was the perfect combo of savory and sweet without being too sweet.

Brunch at Sweet Diner in the Historic Third Ward

By noon, there was a line to get in and I could see why. This spot was a gem.

Milwaukee River and Historic Third Ward:

After a brunch full of cheese, sausage and chicken – we needed a good walk.

The Historic Third award is gorgeous. It has a beautiful Milwaukee river, some cute shops and of course, the Milwaukee Public Market.

The Milwaukee Public Market was the most happening spot Saturday morning for a special fall festival – it spanned on block and had homemade caramel apples, pumpkin ale, face painting and a make your own scarecrow station. We did all of the things and it put us in a fall mood.

Mid Day Break

We took our pumpkins, our scarecrow and our cold selves back to my friend’s condo for an espresso at home. I get that there’s only so much daylight in a day, but vacation is both about exploring as it is about relaxing.

We went back into the world and this time, through the downtown area across town. It was nice that Milwaukee is a very walkable city. It took us about 25 minutes to walk from the Historic Third Ward to the West Town and Haymarket area.

Milwaukee is a sports town, and I learned that everyone stops and watches the Milwaukee Badgers. The Haymarket area is the perfect spot for entertainment and sports bars. They have Punch Bowl Social, which has a lot of games, and then the area has a lot of modern bars with an outdoor space to grab a beer and watch the game on a big screen.

Milwaukee Lakefront Brewery Tour

Since we’re not sports bars girls, we headed northwest for a brewery tour at Milwaukee Lakefront Brewery. We checked online and their tour was sold out, but when we got there they had a mini tour, which is about 20 minutes and you still get 4 drink tickets for $3 less. So, for $8 we learned that women invented beer and had a very good evening.

Lakefront Brewery is like one big mess hall, but they have some of the best beers I have ever tasted. They have a really good gluten free beer that was light and refreshing like a cocktail. I recommend the Eastside Dark – it’s dark in color but it’s actually a light beer.

They also have award winning cheese curds. If you have friends to share, get the Mac and Cheese. We literally copied the couple next to us, because it never hurts to do as the locals would do.

Mac and Cheese at Lakefront Brewery

We sat outside for a minute because they have a river view and we also made friends 🙂

Three guys were visiting from Minnesota and started talking to us. After our tour we talked with them for hours about the best fairs in America – apparently Minnesota has the second best state fair.

By this time, we had walked almost all of Milwaukee and drank all their beer and ate all their cheese. So we walked the two miles back and decided to Netflix and Chill. Because it was like 7 pm and it was cold.

The guys from the brewery went to a comedy show and then I threw an impromptu party at my friend’s condo, inviting everyone we met that day to her house. It turned out quite well. And then I woke up early the next day to take my train back to Chicago.

Amanda Whitfield
Amanda Whitfield

Amanda Whitfield is a writer and speaker and a relationship builder. She believes that meeting people in person is important. After attending numerous fashion, startup, and creative events, she founded Windy City Cosmo is 2015 to help people make connections in the city as they build their businesses, start and end relationships and see and be seen. Over the past three years, the entrepreneurs she’s interviewed have become the most successful in Chicago and Windy City Cosmo won an award in 2017 for her work for female entrepreneurs.

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