We recently took a trip to Milwaukee, WI to meet up with our friends, Meredith and Spencer, and celebrate Spencer’s 30th birthday! We had never been to Milwaukee but really enjoyed our time here. There is plenty to do, but it felt way less crowded/busy compared to other Midwest cities. We were also blessed with incredible weather, although slightly windy/chillier than anticipated at some points. Still – can’t complain at all!
We stayed at the Homewood Suites downtown and felt it was the perfect location + a really nice hotel with tall ceilings and plenty of space. The only downside is parking (like many hotels in cities), we had to pay $50 for parking in a garage that wasn’t technically connected to the hotel. Depending on which areas you plan to explore, this city is very walkable. We left our cars parked in the garage all weekend and only got a few rides the whole time.
Ahead of our trip, we purchased Pub Passes online for half off ($12.50/person), which included a free beer at several breweries around Milwaukee. We definitely got our money’s worth on these, but could have been even more intentional about visiting additional spots on the pass.
Day 1 / Friday
We arrived around 2pm, checked into our hotel, then walked over to Cafe Benelux for a late lunch. We sat on the rooftop and despite the crazy wind, it was an enjoyable experience. Their beers and Bloody Mary options are two reasons you should check this place out!
We then ventured across the street to the Tiki Bar at the Milwaukee Public Market. The Tiki Bar is a super tiny area which means it was jam packed with people, but that kind of made it fun! We returned here on our second day to try Oyster Shooters (it felt like an important experience to have), and while they weren’t delicious, I do think they’re worth trying if you’ve never had one.
We continued our exploration by walking around the Historic Third Ward. The streets are well-kept and filled with greenery and flowers, which I loved.
We were ready for something besides beer so ventured to The Outsider, a rooftop bar in the Journeyman Hotel. It was time for espresso martinis to keep up the energy, so we enjoyed those on the bumpin’ rooftop.
We had dinner reservations at Blue Bat Tequileria and opted to sit outside, even though it was a bit windy and chilly when the sun went down. I would highly recommend sitting along the river, though! I’m such a sucker for anytime I can be by the water and enjoy great company + drinks + food. You really can’t go wrong with anything on their menu.
It was time to get a stamp on our Pub Pass, so we walked over the bridge to The Explorium Brewpub for a nightcap brew. This was more of a classic pub, which was a nice change in scenery. And since we were tapped out from a day of travel and drinking, we headed back to the hotel for some shut-eye before another day of exploring!
Day 2 / Saturday
If you’re up for it, I recommend starting your day with a run, jog, or walk along the Milwaukee River Walk! We started at the entrance to N Riverwalk Way off of N Water Street (steps from the hotel), and ran along the River to the Milwaukee Pierhead Lighthouse, then looped around along Lake Michigan and towards the Milwaukee Public Market. Our loop was about 3 miles. We then refueled ourselves at Colectivo Coffee, which is sooooo good, and walked around the area a bit more.
We went back to the hotel to freshen up for the day then grabbed a ride to Lakefront Brewery, which sadly isn’t on the Pub Pass, but definitely worth the visit. We opted for lunch and a beer here while sitting along the river. It couldn’t have been a better day for us!
To walk off the cheese curds (a must get!), we made the 1.5 mile trek along the river to Pilot Project Brewing (and sat on the rooftop). We passed by the Milwaukee Bucks stadium on the way, too!
Again, I was a little beer-d out and ready for a cocktail, so we grabbed a ride to Great Lakes Distillery and Taproom, the one spot on your Pub Pass you can get a free cocktail on tap. The bartender was very friendly and allowed us to get any cocktail we wanted.
We had dinner reservations so headed back to the hotel to regroup before the big birthday celebration at an Italian restaurant, Il Cervo, which I cannot recommend enough. It has a large rooftop patio area with lovely views of the city and great drinks. We sat inside for dinner, where we loved every single dish we had (I especially recommend the Creste De Gallo and chicken parmesan) and ended with a night cap back on the rooftop patio. Their Black Manhattan, Dirty Martini, and Espresso Martini were fan favorites from our group.
Day 3 / Sunday
Sadly we were heading home on Sunday, so walked over to The Wicked Hop for a quick breakfast and fuel for our drive home. We wanted to get in a few steps before hopping in the car, so walked again to Lake Michigan just to soak up some Vitamin D and see the water one more time. We also stopped in Milwaukee Public Market to get some pastries/goodies to take home with us!
We had a great weekend getaway in Milwaukee and feel there is even more to explore than we had the time for! I love checking new destinations off our list (and states, too) so was really glad to try somewhere new with great friends.