One of my best friends Kate is from Milwaukee, so I’ve had the pleasure of visiting many times and it never disappoints! If you’re looking for a quick escape from Chicago, Milwaukee is only an hour and a half away and makes the perfect charming weekend getaway. You may be surprised at how much this city has to offer!
WHERE TO STAY :
Kimpton Journeyman Hotel: The Kimpton Journeyman is a new downtown Milwaukee hotel right in the heart of the historic Third Ward district. We had the pleasure of staying here for a weekend and were very impressed. The decor is impeccable, the service outstanding, and the location couldn’t be better. The rooftop also has an amazing indoor/outdoor bar and restaurant with great food, craft cocktails and gorgegous craft fire pits. We’ve made it a point to stop here every time we are in Milwaukee regardless of if we are staying a the hotel or not.
WHERE TO EAT:
Saint Paul Fish Company: The Saint Paul Fish Company is conveniently located right inside the Milwaukee Public Market and one of our favorite places to go whenever we visit. They have an indoor oyster bar that is perfect for the winter months and an outdoor Tiki bar that is amazing in the summer. They also have a market where you can buy all of the fresh fish to take home and make yourself. Our favorite menu items are the lobster Bloody Mary, calamari steak, lobster roll, and the Jamaican jerk swordfish sandwich. Don’t be surprised if you find yourself here more than once in a weekend.
The lobster roll
The lobster Bloody Mary
Odd Duck: If I ever opened a restaurant I would want it to be just like Odd Duck. The menu is constantly changing and each dish more delicious than the next. All of the menu items are shareable, small plates which makes ordering fun. We come here almost every trip because the food is never the same, but always amazing. Their menu is inspired by both local ingredients and world cuisine with plenty of options for vegetarians, vegans and omnivores alike. Do not miss this gem!
Handmade rabbit agnolotti
Lobster corn fritters with chili lime crema
Ardent: If you’re looking for an amazing new American tasting menu for a fraction of the price of most upscale Chicago restaurants, this is your place. We came here as part of my birthday weekend celebrations and it was such a delicious memorable experience. The restaurant itself seats about 20 people and if you ask in advance you can sit right at bar looking in to the kitchen. The service is outstanding and lacks the stuffy vibe that comes with so many tasting menus. Make a reservation here well in advance!
Dan Dan: If you’re in the mood for delicious Chinese food and craft cocktails in a fun atmosphere, Dan Dan is your spot. The restaurant is actually owned by two chef’s named Dan. We tried so many things on the menu and they were all great! Order the Sichuan pork dumplings, the short rib and foie gras pot stickers, and the 3 course Peking duck dinner. I’m still dreaming about the duck wonton soup with truffle bone broth.
Cafe Benelux: Come for the rooftop, stay for the snacks. If you’re in the mood for sipping great Belgian beer or rosé in the sun, Cafe Benelux is your spot! We usually will stop here for a few appetizers and some sunshine when the weather permits. Cafe Benelux is conveniently located right in the 3rd ward across from the Milwaukee Public Market. Make sure to get at least one order of their frites with one (or a few) of their seven dipping sauces.
Mussels & frites
Choose from their list of 7 different Bloody Marys
La Merenda: Globally inspired tapas and a fun, colorful atmosphere makes La Merenda the perfect spot for a group dinner or celebration. According to their website, La Merenda means “early snack” and refers to an Italian custom of early evening socializing and gathering to share food and drink amongst friends and family.
Wolf Peach: Wolf Peach offers both a beautiful view and some amazing food. If you get the chance during the summer take advantage of the outdoor seating. The spot is great for both brunch and dinner.
Harbor House: Harbor House is located right on Lake Michigan and offers one of the best views in Milwaukee. They offer happy hour Monday through Friday and a seafood brunch on Sundays. Sit on the patio, sip wine, and order a few pounds of their peel n’ eat shrimp. Or indulge in their happy hour prix fixe which includes 3 happy hour oysters, beer battered hake, garlic parmesan fries, and a can of Schlitz for 10.95. It doesn’t get much better than that.
Colectivo Coffee: Colectivo Coffee Roasters is a specialty coffee roaster based in Milwaukee with a handful of stores in the area. We usually stop at Colectivo a few times during our trips to Milwaukee for a quick pick me up. Their coffee is delicious. If you’re looking for something more unique than a latte, go for their nitro cold brew — it’s delicious and full of caffeine.
WHERE TO DRINK:
The Outsider: The Outsider is my favorite place for drinks in Milwaukee. It’s is located at the top of the Kimpton Journeyman Hotel in the 3rd Ward and has both a beautiful inside bar area and the perfect outdoor space equipped with multiple fire pits, blankets, and views. The cocktails, service, and snacks here are all pretty great. They tent off the outdoor area in the winter, so it can be enjoyed during all seasons!
Indoor bar at The Outsider
Winter at The Outsider — Still cozy!
The Tin Widow: If you’re in the mood for a unique hole-in-the-wall bar with lots of character and an extensive spirits list, go to The Tin Widow. The decor is darling and the drinks are great! They offer more than 100 different gins and an equally impressive whiskey selection. Make sure to check out all the interesting pieces that make up their gallery wall.
Gallery wall at The Tin Widow
Behind the bar at The Tin Widow
At Random: YOU MUST COME HERE. Please. It’s really an experience like no other. Nestled in the residential neighborhood of Bay View, At Random is worth the Uber ride. Prepare to take a step back in time, as At Random has the same waitresses, decor, and barkeeps that ran the place in the 1960’s. Their specialty is nostalgic boozy ice-cream cocktails. Take your sweetie back in time to this adorable spot. Also, its cash only.
The interior of At Random
Swig Wine Bar: This super cute wine bar in the 3rd ward if the perfect stop for drinks before dinner. Order two different wine flights with your significant other and swig away.
Camp Bar: This “up north Wisconsin” themed bar is perfect for football watching, day drinking, and taxidermy. Come with a crowd for a loud, rambunctious time. Dogs are allowed.
Camp Bar
Bugsy’s Back Alley Speakeasy: This 1920’s themed bar is always a great time with show stopper dancers on stage and live music from Thursday through Saturday. You may have a little trouble finding the entrance, but just remember that you should be taking “back alley” quite literally.
Barnacle Buds: If you plan on spending a day on the Milwaukee River, you must stop at this bar. The beach shack and picnic tables here will have you feeling like you’re vacationing in the Florida Keys. You’re coming here mostly for this environment and some drinks, as the food is just okay. The perfect spot on a sunny, summer day.
WHAT TO DO:
Rent a pontoon and cruise the river. The river is a good time with plenty of food and drink stops on the way. Dock your boat and enjoy. Just remember to bring along a sober captain.
Explore the historic third ward. The Third ward is home to many of the stops on this city guide and my favorite area in the city. If you can, stay here so you can conveniently walk to almost everything!
Bike the lakefront. Rent bikes from one of the many stations around the city and hit the lakefront path. Stop for lunch at Harbor House, right on the water.
Summerfest. 11 days, 11 different stages. This music festival is a held right along the lakefront and hosts as many as 800 acts.
Glorioso’s Italian Market. Located on Brady Street, this amazing Italian market is worth a visit. If you’re a foodie, this place is heaven on earth. Grab one of their delicious Italian sandwiches (the human torch or the meatball bomber), some of their house-made Italian sausages, and a few sweets from their bakery case.
Visit the Milwaukee Art Museum. If you’re biking the Milwaukee lakefront or stopping for lunch at Harbor House you might as well visit the iconic Milwaukee Art Museum. The architecture of this building alone is a reason to visit.
Go on a brewery tour. Milwaukee is a city that is famous for its beer culture, so a brewery visit is a must. Lakefront Brewery offers multiple tours every day and a relaxing spot to drink on the river once you are done.
Friday Fish Fry. If you don’t know, Friday fish fry in Wisonsin is a thing. A glorious thing. Check out this article for a list of the best Friday fish fries.
Milwaukee Public Market. Foodie heaven. Twenty or so vendors pack the Milwaukee Public Market with some seriously tasty food and culinary shopping. Come here hungry or maybe don’t, because either way you’re going to leave with a lot of food. Milwaukee Public Market is home to my favorite Saint Paul Fish Company.
Walk Brady Street. Come hungry, leave happy. Brady Street is the perfect place to food crawl. The street boasts a number of restaurants that can accommodate any taste.
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