Milwaukee has gone by many nicknames over the years: Cream City, Brew Town, the German Athens. But a lesser-known, more local handle — Smallwaukee — may best capture the personality of this Wisconsin city of 600,000, which can feel like a small town in big-city clothing, embodying the advantages of both. The fortunes of the Bucks and Brewers are followed in unpretentious taverns that wouldn’t feel out of place on a rural crossroads, and traditional meat-and-potato eateries are as patronized as the latest farm-to-table restaurant. The sleek new Hop streetcar line can take you to the Milwaukee Public Market, with its array of local foodstuffs, or within walking distance of the Santiago Calatrava-designed Milwaukee Art Museum, one of the most beautiful repositories of art in the world. Smallwaukee will grow very large indeed next July when the Democratic National Convention descends upon the city, with downtown’s new Fiserv Forum as its epicenter. The convention’s choice is sneakily apt. Terms like progressivism and democratic socialism, which add crackle and spark to today’s national political conversation, are not academic concepts here. The city elected Socialist mayors for 38 of the last century’s 100 years, and sent the first Socialist, Victor Berger, to the House of Representatives in 1910. And, rest assured, they were the kind of politicians you could have a beer with.
1) 3 p.m. Celebrating bobbleheads
Five dollars will gain you access to the curious new National Bobblehead Hall of Fame and Museum, which opened in February, but is already home to more than 10,000 bobbleheads, the jokey plastic figurines with oversize, spring-loaded heads. A good percentage of those came from the collections of the museum’s co-founders, Phil Sklar and Brad Novak, but many more have been donated. Most are sports oriented, as you might expect, but there are outliers, like the casts of “Duck Dynasty” and “Home Alone.” Next year will bring a political exhibition, with bobbleheads representing every president (bobbing Martin Van Buren, anyone?) and many of the candidates seeking the nomination.
2) 6 p.m. Old World Serbian dining
If you have a car, take the Daniel Hoan Memorial Bridge to the popular Bay View neighborhood. The 1977 span, named after Milwaukee’s longest-serving Socialist mayor, is the city’s most visible tribute to its progressive past. The Serbian restaurant Three Brothers, which opened in the 1950s, predates the recent resurgence of Bay View by several decades, but remains a vital member of the community. It is situated inside a tavern that was once tied to the Milwaukee-based Schlitz brewery, and seems to rise up out of nowhere at the end of a quiet residential block. (Check out the Schlitz “belted globe” symbol on the roof). Inside, ceiling fans slowly spin over a small collection of tables and a long, mural-backed bar. An Old World atmosphere and pace prevail. You are advised to leave your rushed schedule behind, as many of the traditional dishes take time to prepare. These include many menu items accompanied by the phrase “served with potato dumplings” and the signature burek ($19.50), a flaky pastry, filled with beef or cheese or spinach. Both waiters and regulars said it can’t be finished in one sitting. Said one diner recently, “I’ve got a few lunches here.”
3) 8 p.m. Sweet drinks
It’s a short walk from Three Brothers to At Random. The bar entrepreneur John Dye bought the half-century-old, oddly named bar (the original owner wanted to be first in the telephone directory) last year and restored it with a museum director’s zeal. The lights are permanently on dim and the midcentury rec-room décor is the definition of cozy. The clapboard facade proclaims it’s the home of “specialty drinks.” Those specialties are mainly ice-cream drinks, a Wisconsin delicacy in which dessert and cocktails meet halfway. Start with a grasshopper or brandy Alexander. One drink is big enough to share; you can flip a coin for the sugar cookie that hangs off the straw.
4) 10 a.m. Basilica of Saint Josaphat
Drive along Interstate 94 through Milwaukee and you can’t miss the looming dome of the Basilica of St. Josaphat. It was finished in 1901, using materials carted up from the structurally unsound Chicago Post Office and Custom House, and served what was then a largely Polish neighborhood. It has been a prominent part of the skyline ever since. It’s worth getting off the highway to tour the vast ornate interior. A detailed brochure leads you through the highlights, including the ornate, white-marble pulpit and the dazzling gold-leaf-covered baldacchino above the high altar.
5) Noon. Pupusas and parks
Just across the street from the basilica is the unassuming El Salvador Restaurant, which is open for breakfast, lunch and dinner and makes a fine pupusa, a thick cornmeal tortilla with various fillings (most are just $2). Grab a few to go and stroll along the large pond that dominates nearby Kosciuszko Park, just one piece of Milwaukee’s excellent public park system. The system was the brainchild of Charles B. Whitnall, a former florist who helped form FTD, served as the city’s first Socialist treasurer and was secretary of the Milwaukee County Park Commission from its beginning in 1907 until 1941.
6) 2 p.m. A dose of Frank Lloyd Wright
Frank Lloyd Wright is Wisconsin’s favorite architectural son, and Milwaukee has its share of Wright works. One block on Burnham Street boasts a whole row of them, modest homes that are examples of the architect’s stab at affordable housing. These six houses were essentially built as model-home showpieces. The one at 2714 Burnham is fully restored; tours are on the half-hour, starting at 12:30 p.m., on Saturdays in the fall (adult admission: $15). Another is actually available as a rental. For something more elaborate, check out Wright’s Annunciation Greek Orthodox Church in nearby Wauwatosa, a circular spiritual spaceship whose large, blue dome mirrors the sky above when the weather cooperates. (To see the interior, your best bet is to visit on Sunday during services.)
7) 4:30 p.m. Drink Wisconsinbly
Fiserv Forum, the undulating new home of the recently ascendant Milwaukee Bucks, will serve as home base for the Democratic convention. Within a stone’s throw away are two very different drinking options. Right across the plaza, in the newly coined “Deer District,” is the Drink Wisconsinbly Pub. The bar grew out of a popular T-shirt slogan that has become the state’s cheeky unofficial motto. It’s a goofy, fun-loving joint. There’s a lot for sale, including T-shirts, hats and glassware. Brandy old-fashioneds are dispensed from a bubbler (Wisconsinese for drinking fountain), and the men’s room is adorned with photos of famous Wisconsinites, including Willem Dafoe, Orson Welles and, er, Kato Kaelin, an actor who was a witness in the O.J. Simpson murder trial.
8) 5:30 p.m. Homage to local history
A few yards south — on Vel R. Phillips Avenue, which was renamed in 2018 after the Wisconsin politician and civil rights activist — is the much older Turner Hall. It was built in 1882 by the Turners, a progressive German athletic, cultural and political association. All three of Milwaukee’s Socialist mayors were Turners. (“A sound mind in a sound body” was the group’s motto.) The grandly dishabille upstairs ballroom may have inspired the still-remembered 1891 pop hit “After the Ball.” The building still performs its original function, but has recently been given contemporary relevance by some snazzy new signage and the arrival of Tavern at Turner Hall, where, if you’re looking for a filling snack, you can order the Milwaukee Mac, a mash up of bratwurst and macaroni and cheese. Be sure to inspect the bar’s 19th-century murals depicting moments in Turner and Milwaukee history.
9) 6:30 p.m. Not just any hotel lobby
A visit to the lobby of the Hyatt Regency serves as a somber reminder that presidential campaigning can go wrong. Here once stood the Gilpatrick Hotel, where Theodore Roosevelt attended a dinner on Oct. 14, 1912. Outside the hotel, he met the gun of a delusional saloonkeeper. Roosevelt’s metal eyeglasses case and a copy of his 50-page speech, tucked inside his jacket, slowed the bullet and saved the bull moose’s life. Though bleeding, he insisted on delivering the speech before receiving medical attention. A detailed display here commemorates the event.
10) 8 p.m. The Original
The Original is one of those cozy, tucked-away restaurants — of which Milwaukee has many — which make you forget the dust and bustle of urban life. There’s been a bar or restaurant on this corner since the 1890s. The Original opened in 2017. The appealing menu — recent menu items included elk and shiitake stroganoff ($25) and a vegetarian chili bowl with smoked tofu, beans, sweet potatoes, parsnips, shiitakes, onion, Cheddar cheese and crème fraîche ($15) — is both traditional and contemporary, familiar yet eclectic, and every dish comes with a smart cocktail, wine or beer pairing recommendation.
11) 10 a.m. Outrageous brunch
There is no need to peruse the food menu at Sobelman’s, a brunch institution in yet another old Schlitz house. Just order a bloody mary; your meal arrives in the form of a garnish as large as the drink (from $9 to $60). The Baconado, for instance, includes a skewer of bacon-wrapped jalapeño cheese balls. The Bloody Beast, served in a large Bell jar, comes with a whole fried chicken balanced atop it. Don’t send back the “schnitt” of beer the bartender sets down. That’s not a mistake. Any Milwaukeean would feel shortchanged if their bloody didn’t come with a sidecar of suds.
12) 11 a.m. Joan of Arc chapel
Milwaukee’s done a decent job of preserving its old structures. But its most ancient building, by far, is this medieval oddity, slipped snugly into the Marquette University campus. There’s a long story behind the tiny church’s journey in 1926 from the Rhone Valley to the Long Island estate of a Joan of Arc-fixated railroad heiress to Marquette in 1966. And the quiet stone refuge, simply adorned with tapestries that predate the building, and stained glass that postdate it, provides just the atmosphere to take it all in.
13) 12 p.m. A beer baron’s mansion
A short walk away is the beautifully preserved mansion of the Schlitz rival, Captain Frederick Pabst. If the Flemish Renaissance Revival structure isn’t enough to tell you how well the father of Pabst Blue Ribbon did for himself back in the day when he was one of the nation’s leading citizens, a tour of the august, dark-wood interior will clinch it. Take note of Pabst’s well-appointed study, which contains an enormous humidor to hold the Captain’s beloved cigars, and secret panels used to stash liquor, documents and whatever else a beer baron might want to hide. (Adults $14).
The Ambassador Hotel (2308 West Wisconsin Avenue) is a recently refurbished Art Deco gem from 1927. There’s a restaurant, cafe and cocktail bar — called the Gin Rickey — on site. Liberace was the house pianist in the 1930s. And Kennedy and the Beatles visited in the 1960s. Rooms start at around $80.
More centrally located is the 1927 art moderne Hotel Metro (411 East Mason Street), another stylishly restored city landmark. It’s walking distance to the Milwaukee Art Museum, the Pfister Hotel, the Milwaukee River and other city landmarks. It’s also close to a stop on The Hop, Milwaukee’s new streetcar system. There is valet parking and the hotel’s French-leaning restaurant Pastiche serves a good breakfast. Rooms start at $128.
For a lively neighborhood experience, bunk in the delightful Bay View neighborhood on Milwaukee’s southside. There are plenty of dining and drinking options, plus a pleasingly relaxed, small-town atmosphere you won’t get downtown. A room can be had for as little as $35 a night on Airbnb.