Road Trip Milwaukee: Where to Eat, Drink & Sleep
The Cream City is worth your time — don't just watch it on Top Chef. Go.
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Despite living two hours south, I can count on one hand — and honestly, I wouldn’t even need all five fingers — the number of times I’ve visited Milwaukee. But I have gone north to Wisconsin countless times since I was a kid for summers at Camp Chi, visiting Madison and Lake Geneva, seeing concerts — so many concerts — at Alpine Valley, hanging out in Kohler, camping and whitewater rafting in the Northwoods — Drew and I even got married in Door County at Gordon Lodge.
The first time I went to Milwaukee, I was young, maybe 10. Possibly younger. I don’t remember much from that family excursion, but I do remember very distinctly going to a restaurant that I swear had a dolphin swimming in a huge tank. Does anyone know what I’m talking about? Am I making that up? OK, maybe not so distinctly.
Drew and I have discussed many times about going up for an overnight to check out some restaurants and especially to visit the Calatrava-designed Milwaukee Art Museum and its spectacular wings that open and close throughout the day. Yet we still haven’t. So when I got invited on a quick culinary-focused media trip to Milwaukee, I jumped at the chance.
We stayed at the very cool Iron Horse Hotel, dined at a number of restaurants, including DanDan, EsterEv, The Diplomat, Birch, and Bavette La Boucherie. We strolled the Historic Third Ward and had drinks at the very classic Bryant’s Cocktail Lounge, Milwaukee’s oldest dating back to 1938. And I took some time for myself to — finally! — visit the art museum, which sits right on Lake Michigan. It was absolutely worth the hour I had and begs a return trip.
I recently wrote up a Milwaukee guide for Time Out Chicago, which included many of these spots and more chic hotels, a speakeasy, a wonderful Italian market, and various things to do.
And I’m sharing it with you here. Why? Because Milwaukee — and Madison, Sheboygan, and other places in Wisconsin — are popping. The upcoming season of Top Chef filmed there with new host Kristen Kish (who
and I interviewed on our podcast Overserved in 2019) and DanDan co-owner Dan Jacobs is a competitor. Set your DVR for the March 20 premiere.While you may think Wisconsin is all about brats, beers, and supper clubs, you wouldn’t entirely be wrong, but there’s so much other fantastic food to be had. With that, here’s your guide. Now don’t be like me and just talk about going. Make plans to head north (or fly in if you’re reading this from anywhere other than Chicago) to Milwaukee, the Cream City. You’ll be happy you did.
A guide to Milwaukee
Where to eat
While historically associated with beer and brats, Milwaukee has so much more to offer. Whether you want a casual grab-and-go snack or a James Beard Award-winning meal, check out these places.
Bavette La Boucherie
217 N Broadway, Milwaukee, 53202
414-273-3375
Is it a market with artisan foodstuffs? A butcher shop? A full-service restaurant. Yes, yes, and yes. James Beard Award-nominated chef/owner Karen Bell moved her 10-year-old restaurant to the historic Third Ward in 2022. The menu is Midwestern at heart with global influences. Start with jamón Ibérico or chicken liver mousse. Throw in smoked trout deviled eggs and potato-crusted octopus with shishitos and chorizo aioli. At lunch, dig into the array of sandwiches (pork belly banh mi or muffuletta anyone)? And dinner offers more composed plates like red snapper with celeriac and mung beans or gnocchi with delicata squash and a lamb ragu. And do we have to even remind you to not forget those beef fat fries?
The Diplomat
815 E Brady St., Milwaukee, 53202
414-800-5816
This spot is a true labor of love. Chef Dane Baldwin, who won the best chef: Midwest James Beard Award in 2022, has worked in hospitality since he was 15. He and his wife, Anna, opened this intimate restaurant in 2017 and have quietly garnered all the accolades for his humble yet flavorful fare. The seasonal menu changes frequently, but a familiarity runs through the dishes. Whether Baldwin’s take on a Big Mac (like, the best you’ll ever have); a lake trout with a bright wintry salad of grapefruit, kohlrabi and radish; or New York strip with shallot puree and king trumpet mushrooms, you can pair it all with a selection from the global wine list and settle in.
Pepperpot
2215 N Doctor M.L.K. Jr Dr, Milwaukee, WI 53212
414-509-5206
Yes, you can get classic Jamaican dishes like jerk chicken, escovich kingfish bites, and braised bone-in oxtail with scotch bonnet peppers and sweet carrots. But chef/owner Dwight Jackson add a modern twist to a few. You can find jerk chicken egg rolls, jerk salmon sandwiches, and chef’s choice dishes like Jackson’s spiced brown stew chicken and his Dem Gwan Talk Bout It Steak, a smoked marinated chimichurri-topped tenderloin served with coconut mashed potatoes and asparagus. Want to explore more jerk chicken in Milwaukee? Check out the Jerk Chicken Trail.
DanDan
360 E Erie St., Milwaukee 53202
414-488-8036
Named for both the spicy Sichuan noodle dish and the two chef/owners, DanDan delivers Chinese soul with Midwestern sensibilities. The restaurant pulls from the Dans’ (Jacobs and Van Rite) childhoods and adds some heat, literally. Start with the five spice chicken wings and scallion pancakes with housemade hoisin sauce. Don’t skip dumplings — either the Sichuan pork or short rib and foie gras. Absolutely get the lipsmackingly spicy namesake dandan noodles and then some silken mapo tofu. If you’re really hungry, call a day ahead to order the three-course $85 Peking duck service for three.
EsterEv
2165 S. Kinnickinnic Ave, Milwaukee 53207
The hidden finer-dining restaurant, which has earned six James Beard Foundation Awards nominations within DanDan will come out of the shadows and into its own space in the Bay View neighborhood. It’ll also go from an eight-course $125 tasting menu the Dans nostalgically create based on memories of their great-grandmothers’ cooking to a four-course $65 menu to open it up to more people. Look for this to open in the spring and yes, the caviar tater tot is making the move, too.
Uncle Wolfie’s Breakfast Tavern
234 E. Vine Street, Milwaukee 53212
414-763-3021
Who wouldn’t want to eat breakfast within the cozy confines of a classic tavern vibe? This daily breakfast and brunch spot elevates your requisite dishes. You can get the Big Wolf Breakfast (eggs, potatoes, choice of meat) or go even heartier for the breakfast poutine with rich sausage gravy; a stack of Johnny cakes; ube toast crunch oatmeal; a savory latke waffle (yes, that’s a potato waffle!), or a juicy patty melt. And yes, you can get all the brunch cocktails and even non-alcoholic tipples.
Vientiane Noodle Shop
3422 W National Ave, Milwaukee 53215
414-672-8440
This family-owned Laotian and Thai quick-serve noodle shop has been drawing crowds for more than 20 years. The casual, simple storefront in the Silver City neighborhood has food that’s anything but casual. Dises pop with color and spice, both flavor and heat. You’ll find typical dishes like pad Thai and pho, but also oxtail khoa poun (rice noodles in red curry with galangal and coconut milk); banh quan (barbecue pork filled crepes; and traditional Laotian fish salad with various herbs, greens, and spices.
Birch
459 E Pleasant St, Milwaukee 53202
414-323-7372
Opening in 2021, Birch set a course for all things fresh — something that might feel impossible in the upper Midwest. But chef/owner Kyle Knall makes the most of seasonal produce and product from local farms to incorporate a shot of freshness year round in the modern, bright, and airy dining room. Get a feel for everything through the seasonal tasting menu or go a la carte for dishes like steelhead crudo with daikon and honeycrisp apple; wood-roasted pork chop with spaetzle and red cabbage; and ricotta and rutabaga-filled pasta with black trumpet mushroom. Add in a truly eclectic wine list with a focus on less common varietals and you have a winner.
Zócalo Food Truck Park
636 S 6th St, Milwaukee 53204
When you want a one-stop shop for a variety of eats from startup-minded food entrepreneurs, this is a great option. From the flagship Tavern to Ruby’s Bagels (“Milwaukee style”) to Modern Maki (sushi and ramen) to Hot Box Pizza MKE, and more, this food truck park is a must hit. And you might think, “A food truck park, in winter?!” They offer these super cute heated huts you can reserve so you can eat without your fingers freezing.
Bacchus
925 E. Wells Street, Milwaukee 53202
414-765-1166
Celebrating 20 years this year, Bacchus is consistently one of Milwaukee’s best restaurants. This Bartolotta group spot, which underwent a renovation in 2020, is at the same time refined and playful. With a massive, award-winning wine list to pair with multi-course tasting menus with classics like chilled king crab, filet mignon with a horseradish cream, pork bolognese, and chocolate truffle, this is a definite special occasion spot.
Where to Drink
When you’re thirsty, here are some of the best spots to get a classic cocktail, a speakeasy experience, a top brew, and more.
Bryant’s
1579 S 9th St., Milwaukee 53204
414-383-2620
When you want a truly unique cocktailing experience there’s no better place in town than Bryant’s. Mixing up drinks and clever conversation since 1938, this no-reservations spot has a seriously deep catalog of cocktails (we’re talking north of 400) and is known for, among many others, its Wisconsin brandy Old Fashioned and array of ice cream cocktails, like the Pink Squirrel, which was created here. This dark and swanky spot takes you back to a simpler place in time with a focus squarely on enjoying cocktails. Go for happy hour Sunday through Thursday for $5 specials. Then go visit their other bars At Random and The Estate.
Lakefront Brewery
1872 North Commerce Street, Milwaukee 53212
414-372-8800
The brewery, which actually sits on the Milwaukee River and not Lake Michigan a few blocks away, has been pouring some of the city’s best brews since 1987. Go by for a pint, a meal, and a tour, which lasts 45 minutes and includes four 8-ounce pours. In warmer months, grab a table outside along the water. This organic-certified brewery offers a friday fish fry — polka included.
GoodKind
2457 S Wentworth Ave, Milwaukee 53207
414-763-4706
GoodKind has been leading Milwaukee’s modern cocktail charge since 2015 and their ever-changing drink list, which often highlights seasonal Midwestern ingredients, is as interesting and diverse as its dining menu. Belly up to the long wood bar set below a vintage tin ceiling for the classic spicy crab pasta or smoked whitefish tartine. Wash those down with a glass of their winter sangria, a mushroom Mai Tai, or a Quebec cocktail with Four Roses bourbon, Rittenhouse rye, Fernet, maple syrup and lemon. That’s like a cozy hug in a glass.
Mosler’s Vault
5900 W. North Ave., Milwaukee 53208
From the team behind Bittercube Bitters, Mosler’s is an intimate speakeasy cocktail bar housed inside the former United Federal Savings & Loan bank vault — a property dating back to 1949. Soak up the history with a rotating and creative cocktail list with spirits ranging from barrel-proof Puerto Rican rum to a house blanco tequila blend and eclectic ingredients like celery syrup, tamari, and Bittercube’s range of bitters.
Things to see and do
With all the eating and drinking you’ll do, you have to work up an appetite. Do it at these places.
Milwaukee Art Museum
700 N Art Museum Dr, Milwaukee, WI 53202
414-224-3200
This is the city’s premier museum and the wow factor starts before you even enter the building, which overlooks Lake Michigan. Designed by Santiago Calatrava, the modern white concrete and glass building sprouts wings at various points throughout the day, which is truly a sight to behold. The collection includes 25,000 works of art by the likes of Georgia O’Keeffe, Rodin, Degas, Monet, Warhol, Picasso, Miró, and many more dating back to the 15th century through today.
America's Black Holocaust Museum
401 W. North Avenue, Milwaukee 53212
414-209-3640
With four main themes set across the museum — remembrance, resistance, redemption, reconciliation — the museum aims to highlight the often-dark history of Black people in America. The ABHM covers historical events stretching from the African slave trade through modern times and tells stories of injustices, redemption, and forgiveness. The museum now sits in the historic Bronzeville neighborhood following the 2022 reopening after the museum received a $10 million anonymous donation. The museum also hosts a 3,200-page virtual museum to continue your journey long after your visit.
Milwaukee Public Market and the Historic Third Ward
400 N Water St, Milwaukee, WI 53202
414-336-1111
Set across 10 blocks, the Historic Third Ward is Milwaukee’s arts district with galleries, shops, restaurants, and entertainment. Plan a day to meander and browse and be sure to include a chunk of time to wander through the Public Market. This vast hall, which opened in 2005, features numerous independent stalls offering everything from wine, barbecue, poke, and smoothies to coffee, seafood, baked goods, and meat and cheese. Retail shops throughout the Third Ward include local men’s and women’s boutiques, housewares, specialty stores, and more. In addition to wandering about the historic buildings, the Third Ward also sits adjacent to the Riverwalk and Lakeshore State Park.
Harley-Davidson Museum
400 W Canal St, Milwaukee, WI 53201
414-287-2789
If you’re a fan of the open road and classic hogs, this is a must stop when you visit the Cream City. Harley-Davidson started in Milwaukee in 1903 and quickly became an iconic American brand. The museum showcases hundreds of motorcycles, even dating back to the earliest days. You’ll see classic bikes and even one that survived a ride across the Pacific Ocean following a tsunami in Japan that swept it away. With bikes, memorabilia, signage, and more, this is a one-of-a-kind experience for a Harley lover.
Glorioso’s Italian Market
1011 E Brady St, Milwaukee, WI 53202
414-272-0540
Before you pop in for a meal at The Diplomat, pad in an extra 20 minutes (or more) to browse this fantastic Italian market, which has operated in the area since 1946. You can get fresh and dried pasta, gorgeous charcuterie, imported olive oil and balsamic vinaigrette, risotto, dried herbs, chocolates, sauces, Italian wine, and so much more. Even if you don’t buy anything (which, frankly, why wouldn’t you?) it’s just a cool place to browse the beautiful products. If you’re in the mood to broaden your culinary skills, Glorioso’s offers classes to teach you how to make pizza, steaks, shrimp scampi, chicken marsala, ravioli, and more.
Where to stay
Milwaukee has some fantastic hotels and inns. Here are just a few of the better places to lay your head.
Saint Kate – The Arts Hotel
139 E Kilbourn Ave, Milwaukee 53202
414-276-8686
Stepping into the centrally located theater district property (with a complimentary glass of bubbles, of course), you’ll wonder if you walked into a modern art museum complete with rotating exhibits or if this really is your uber-cool hotel. With contemporary art throughout the public spaces and guest rooms, this property is a gallery within itself. With comfortable pet-friendly accommodations, the Saint Kate offers 219 apartment-like rooms, including four specialty suites designed by local artists. Music plays almost-equal importance as the art with record players with a selection of vinyl and ukuleles in each room. So spin a disc and kick back in your living area after pampering yourself in the oversized walk-in showers with spa-style products. The hotel boasts five on-site restaurants and bars: the ground-level Proof for Neapolitan-styles pizza; The Bar, off the lobby, for all-day dining and drinking; the contemporary American Aria with attached Champagne and wine bar, Giggly, on the second floor; and the supper-club vibed The Dark Room, bookable for private events up to 25 people. When it comes to chic, unique hotels, it doesn’t get better than this.
Iron Horse Hotel
500 W Florida St., Milwaukee 53204
414-374-4766
Steps from the Harley-Davidson museum, this 100-room, 100-year-old warehouse loft-like dog-friendly property is a motorcycle fan's dream. The oversized suite-sized guest rooms have a rebel edge with leather-covered headboards and benches, exposed brick and wood beams. And while you will want to explore the city’s vibrant dining scene, you almost don’t have to leave the property. From the hearth-driven Ash (with a four-course wagyu beef tasting menu) to lobby pub Branded to the seasonal outdoor Yard, options abound here. On-site motorcycle parking included, of course.
Kimpton Journeyman
310 E Chicago St., Milwaukee 53202
414-291-3970
There’s no better way to experience the Historic Third Ward than by staying right in the heart of it. This modern nine-floor, pet-friendly boutique hotel has 158 guest rooms and suites with views stretching out over the city. Rooms are outfitted with plush bedding with Frette linens, local artwork, yoga mats, modern bathrooms with walk-in showers and free-standing tubs, and some have living areas with deep lush couches. The common areas feature fireplaces and plenty of cozy seating to kick back. Want an even better view? Pop upstairs to rooftop bar The Outsider for cocktails no matter the weather. Or book a meal at Tre Rivali for Mediterranean-inspired fare.
The Tin Widow is another great bar; they have an extensive whiskey list.
Nice list. I always stay at the Pfister or Hilton City Center, two great old hotels.