Once upon a time, some friends and I tried to go to Canada for New Year’s Eve. The concept was magical, if a little bit of a logistical nightmare for the dead of winter in the North. Ultimately, due to sickness and a winter storm, the plans were cancelled at the last moment and we laughed about it for years to come. Then, a slightly different group made plans to travel to Canada this summer to experience Niagara Falls in all their glory in the height of summer. This time, an unknowingly-expired passport caused us to somewhat less hilariously pivot (side note: the expedited renewal process did work out, the stress was just a bit too much to wait it out).

As I’ve learned time and again, sometimes the plan Bs of life are even better than the initial plans. We switched our anticipated location to somewhere near Lake Michigan for convenience. From our somewhat limited options, we found a very cute AirBnB in the Bayview neighborhood of Milwaukee, Wisconsin, for dirt cheap. Seriously, I don’t think I’ve ever spent that small of an amount on better-than-average housing (less than $30 per person per night for a super cute guest cottage). So, off we drove for a much shorter road trip than initially planned (still long enough to require a bathroom stop), and we arrived to the city in time for a late lunch.

Over the course of 4.5 days, we did a mix of wandering, art-admiring, hiking, beaching, coffee-ing, pickleball playing, baseball game watching (the Brewers lost ironically to the Toronto Blue Jays), eating and hours of lounging in convenient outdoor seating areas. It was a great vacation vibe for our group and there were plenty of pretty places to see around the city. By my standards, Milwaukee was ideal for a relaxed trip with friends or family. Everything we wanted to do (based on very scientific TikTok research) fell within an 8-20-minute car ride and parking was pretty easy most places.

Overall, Milwaukee was pretty great. I didn’t have a single dud of a meal the whole time. As a lover of Chicago, I did find myself unfairly comparing the “Cream City” to the “Windy” one, probably too much. Chicago just is a top tourist destination and it really looks and feels like one. Milwaukee, on the other hand, felt like a distant cousin that is trying hard, but not quite keeping up appearances.

For a little Midwestern weekend getaway, I would definitely recommend a trip to Milwaukee for first-timers, but I’m not sure I would make it a top destination for a return journey.

Note: the highways were SO confusing around Milwaukee. Plus, our GPS systems frequently “lost” us on seemingly simple pathways. Consider screenshotting directions or grabbing a map. I read somewhere that many people take the train from Chicago to Milwaukee, which sounds great, but I feel like you would need a car or have to Uber everywhere.

The Highlights

Milwaukee Art Museum (this really was my favorite part—I loved seeing lesser known works by internationally renowned artists). Cheese curds (my favorite were ordered at Lakefront Brewery). Other top restaurants: Café Benelux, Uncle Wolfie’s Breakfast Tavern, Sweetdiner and Allie Boy’s Bagelry. Atwater Beach. Seven Bridges Trail (there are actually 10 bridges). Pickleball courts behind Dale-Zs. The Riverwalk. Milwaukee Public Market. Mitchel Domes Conservatory. Historic Third Ward. Purple Door Ice Cream. Babe’s Ice Cream. Colectivo (the reigning coffee king), Stone Creek Coffee and Anodyne Coffee Roasting.

SDG

LMB #6