CITY GUIDE
A local’s guide to Milwaukee
- By Evan Rytlewski
- Photos by Jenny Bohr
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At some point, Milwaukeeans began to realize they love it here. Over the past two decades, the city has shed its inferiority complex, retiring the old narrative about being stuck in Chicago’s shadow and replacing it with one trumpeting homey charms. Of course, it’s not a coincidence that the surge in civic pride has correlated with the city’s rising fortunes. Milwaukee has spent the new millennium leveling up, redeveloping its downtown after years of stagnancy, maximizing its abundant waterways, adding a streetcar system and building a prized new arena.
Thankfully, these upgrades haven’t come at the expense of the city’s historic character. Yes, you’ll find craft cocktail lounges, ax-throwing bars, late-night ramen and all the usual bellwethers of a thriving creative class here. But what makes Milwaukee special is the intersection of old and new, its marriage of blue-collar traditions, Old World comforts and modern innovations. And if you’ve never been, it’s also a much greener city than what you may be picturing, with a prized park system and a spectacular lakefront that’s put to great use during the summer.
Meet Evan Rytlewski
A Milwaukee native, Evan is the web editor for the nonprofit Radio Milwaukee. For more than a decade, he was an arts writer and music editor for the city’s alt-weekly Shepherd Express.
Want to get in touch?
Email bytheway@washpost.comRead more about Evan
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Walker’s Point
No one Milwaukee neighborhood gives a complete portrait of the city, but Walker’s Point comes closer than most. In addition to prestigious restaurants, this centrally located district is home to some of Milwaukee’s bustling sports bars, liveliest gay clubs and tastiest tacos. Find this neighborhood.
Brewer’s Hill
Nestled near Bronzeville and Riverwest, Brewer’s Hill may not be as densely populated with local businesses as those cultural havens, but this historical, largely residential neighborhood offers spectacular overlook views of the city and easy access to the Beerline Trail, which connects downtown to scenic riverside spots. Find this neighborhood.
Neighborhoods
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Eat
McBob’s Pub & Grill
Yes, it’s a bar, but this welcoming Irish pub in Washington Heights also serves the neighborhood’s heartiest breakfasts and spectacular corned beef. If you’re planning on a light lunch, order the McGinnity — a mound of eggs, potatoes and crispy corned beef hash — and instead of toast, opt for one of the homemade breads or scones (for being so tiny, this kitchen doesn’t cut corners). If you wash it down with Guinness, nobody will judge.
BTW: McBob’s has a free shuttle to Milwaukee Brewers games, making this an ideal place to fill up before a visit to the field.
4919 W. North Ave., Milwaukee, Wis. 53208
Coffee Makes You Black
Chicken and waffles is the go-to order at this spacious all-day breakfast spot in the North Division neighborhood. The chefs specialize in other soul-food dishes that can be hard to find elsewhere in the city, including catfish and grits and salmon patties and rice. Adorned with vibrant African art, the space hosts poetry readings, community talks, live soul and jazz music, and pop-up shops from Black artists and entrepreneurs.
BTW: They also serve a seriously underrated fish fry on Friday nights.
2803 N. Teutonia Ave., Milwaukee, Wis. 53206
Solly’s Grille
Butter burgers are a regional favorite, but no Milwaukee grill takes them to anywhere near the indulgent extremes of this old-school lunch counter. Solly’s crowns its beef patties with such a heaping scoop of butter that it melts off the burger, leaving behind a glistening pool on the plate. A love-it-or-hate-it experience, this greasy spoon has been dividing locals for more than 80 years.
BTW: You can order your burger with light butter — and if you’re on the fence, that’s probably the way to go.
4629 N. Port Washington Road, Milwaukee, Wis., 53212
Zócalo Food Park
With its sunny patio and picnic tables, this Walker’s Point food truck park is paradise on a nice day. Its vendors do the space justice, offering a variety of scratch-made bagels, ice cream flavors, burgers and arepas (a piping-hot Venezuelan sandwich made from freshly grilled maize dough). For those who prefer to sit indoors, there is also a cheerful, Frida Kahlo-inspired cocktail lounge that comes to life at night.
BTW: Stumped about what to order? You can never go wrong with al pastor tacos from Mazorca, one of the city’s most dependable taco trucks.
636 S. 6th St., Milwaukee, Wis. 53204
Five O’Clock Steakhouse
Meals have an unusual rhythm at this jumping supper club. Diners order while enjoying a drink at the bar, and by the time they’re escorted to the table, their salad is already waiting for them, along with a customary relish tray and a loaf of warm sourdough. With its dated wood paneling, Christmas lights and mirrored walls, the setting is borderline kitschy, but the food is serious — especially the steaks, which are charbroiled for a magnificent crust.
BTW: Five O’Clock’s bartenders specialize in classic cocktails, the most popular of which are, hands down, brandy Old Fashioneds, the unofficial state cocktail.
2416 W. State St., Milwaukee, Wis. 53233
The Noble
Every trip to the Noble is a leap of faith since the menu changes daily. But this tiny farm-to-table restaurant has a kitchen you can trust, with daily specials that include enormous filets and pork chops, creative and hearty vegetarian dishes, and standout seafood (the chefs work miracles with trout and swordfish). If you’re looking to eat on the lighter or cheaper side, the scratch-made soups and rotating selection of grilled breads and spreads are satisfying enough to make a meal of them.
BTW: The Noble doesn’t take reservations, but the waits aren’t terrible if you prepare. Arrive early and plan on a drink at the neighboring corner bar until your table is ready.
704 S. 2nd St., Milwaukee, Wis., 53205
Boone & Crockett
Adorned like an improbably upscale hunting cabin, this roomy-yet-nook-filled Walker’s Point bar serves sensational gourmet cocktails at reasonable down-to-earth prices, along with a huge selection of whiskies and craft beers. A favorite hangout for local musicians (there’s a large concert venue in the back), it takes advantage of its prime riverfront location with a vast patio and a taco truck, Taco Moto, that serves remarkable Dr. Pepper-braised pork tacos.
BTW: The bar is the home base for the Pedal Tavern party bikes that cruise the city during the warm weather months, so it can draw some revelrous daytime crowds.
818 S. Water St., Milwaukee, Wis., 53204
At Random
While neighboring bars expand their draft lines and embrace the latest cocktail trends, this early ’60s relic remains proudly stuck in the past, with amber lighting, vinyl booths and retro decor that suggests a working-class imagining of the kind of cocktail lounges the Rat Pack might have frequented. Ice cream drinks are its signature, and the bar makes an especially tasty grasshopper.
BTW: New owners saved this gem from extinction in 2018, and thankfully they haven’t changed much. One welcome improvement: They now offer non-dairy ice cream cocktails.
2501 S. Delaware Ave., Milwaukee, Wis., 53207
LOCALS THINK YOU SHOULD KNOW
- There’s no sugarcoating it: Winters can be rough. The city shines in the summer, which it marks with street parties and ethnic festivals.
- Even if you’re lukewarm on baseball, American Family Field, where the Brewers play, is a must. Relatively cheap tickets are available for most Brewers games, and the tailgating before is often downright epic.
- Summerfest, a marathon of 11 days of music spread across eight big stages on the lakefront, is an incredible value proposition. Daily lineups are a touch thinner than at festivals such as Coachella, but Lizzo, the National, Brandi Carlile and Lil Uzi Vert have headlined recently. Tickets start around $20.
Do
Estabrook Beer Garden
In its early years, Milwaukee’s public parks were dotted with lively beer gardens. That tradition died with Prohibition, but Estabrook Park reclaimed it in 2012, with a first-of-its-kind biergarten serving sausages, pretzels and German beers in actual glass steins. Similar beer gardens have since popped up all over Milwaukee County, each of them with its own character, but Estabrook’s spectacular river view makes it the most enchanting.
BTW: You can bring the family. A nearby kids’ play area and dog park translate into an idyllic retreat on a summer afternoon.
4600 Estabrook Pkwy., Milwaukee, Wis., 53211
Sherman Phoenix
Like its namesake bird, Sherman Phoenix was born of fire. After a Sherman Park bank building burned during unrest sparked by a 2016 police shooting, a network of investors and entrepreneurs banded together to rebuild the space as a hub for Black-owned businesses. Its scale is remarkable: There are more than two dozen tenants, including a yoga studio, a dojo and an apothecary, along with multiple boutiques and beauty salons. Busiest of all is a food hall featuring a pizzeria, juice bar and health-conscious spring rolls.
BTW: Vegans take note: Next Level Vegans serves a full menu of soups and salads, as well as plant-based renditions of comfort foods such as gyros and macaroni and cheese.
3536 W. Fond du Lac Ave., Milwaukee, Wis., 53216
Oriental Theatre
With its grand balcony and East India-themed art, this gilded, Depression-era movie palace has long been one of the city’s treasures. But since the organization behind the enormously popular Milwaukee Film Festival took over its operations in 2018, it has also become the center of the city’s burgeoning film scene, hosting a year-round lineup of specialty programming and midnight screenings along with the latest arthouse favorites.
BTW: There’s a curated art gallery hidden in the alley behind the movie theater. The setting may be non-traditional, but Black Cat Alley showcases some spectacular murals.
2230 N. Farwell Ave., Milwaukee, Wis., 53202
Deer District
As part of their pitch for the city’s new basketball arena, Fiserv Forum, developers promised to turn the acres surrounding the arena into a year-round entertainment block. They have made good on their word. In addition to several multi-story bars and restaurants that do huge business before Bucks games, the Deer District plaza hosts a beer garden, outdoor movies, yoga and music during the summer, haunted houses in October, and a bustling Christmas village in December.
BTW: Beer lovers should make their first stop at Good City Brewing, one of the city’s most esteemed new breweries.
1134 Vel R. Phillips Ave., Milwaukee, Wis., 53203
Oak Leaf Trail
The pride of Milwaukee County’s extensive trail system and part of the fabric of life for local joggers, cyclists and hikers, the Oak Leaf Trail weaves across the entire county in a crisscrossing loop, with its more breathtaking stretches running parallel to Lake Michigan shoreline. There’s no better way to take in the city’s lakefront and its accompanying parks and beaches.
BTW: If you need a break from the city, head south down the Oak Leaf to Grant Park, where the Seven Bridges Trail offers some of the most picturesque hiking in the county.
McKinley Beach, Milwaukee, Wis., 53202
Lakefront Brewery
Milwaukee is now crowded with craft breweries, but when it opened in 1987, Lakefront Brewery was one of the first. Its well-oiled brewery tour is still the gold standard, with more generous pours and livelier guides than many of the newer tours that have sprung up over the years. After your tour, hang around for some cheese curds or the popular Friday fish fry, which features live polka.
BTW: Make your first beer a Riverwest Stein, an assertive but sessionable dark lager that pairs well with just about everything.
1872 N. Commerce St., Milwaukee, Wis., 53212
Evan Rytlewski
A Milwaukee native, Evan is the web editor for the nonprofit Radio Milwaukee. For more than a decade, he was an arts writer and music editor for the city’s alt-weekly Shepherd Express.
Jenny Bohr
Jenny is a photographer based in Milwaukee. Raised on the city’s south side, an area where she still calls home and can’t stop photographing because of its vast uniqueness. She likes her city’s historic architecture and green spaces.