1. Where to Stay
Go industrial at The Iron Horse (from $149), where spacious rooms feature masculine details like leather headboards and iron hooks, and you can fall asleep to the gentle chug of the railroad that runs next to the building (for a quieter night, book a southeast corner suite facing the warehouse district). Stay up late at the buzzing lobby bar playing a game of billiards on the vintage 1912 table while sipping Manhattans ($10) made with the hotel’s own rye whiskey recipe, Barrel 1907, distilled and barreled in collaboration with neighboring Great Lakes Distillery.
Stay around the corner from Milwaukee Street’s stylish restaurants at the green-certified Hotel Metro (from $169), which is housed in a 1937 art deco building downtown. The property’s 65 rooms are outfitted with sustainable wooden furniture and carpets made from recycled fibers, while three of the five 720-square-foot master suites (from $229) have whirlpools and fireplaces.
Step back in time at the Pfister (from $199), a Romanesque Revival building erected in 1893 and decked out with marble staircases, brass chandeliers, gilded ceilings, and the largest Victorian art collection of any hotel in the world. Upstairs, rooms are divided between the historic section, which was renovated less than three years ago, and a circular tower added in 1963 with direct views of Lake Michigan from the suites ending in 09.
2. Where to Eat
Eat breakfast at the horseshoe counter facing the open kitchen of Cafe at the Plaza, the classic diner that was renovated last year. The refresh also brought in chef Karen Bell, who owned a California-style eatery in Madrid before returning to her hometown. Dishes incorporate fresh produce from Braise RSA (essentially a CSA for restaurants); try the scrambled eggs with Lake Michigan–caught trout ($8.95).
Head to Honeypie for made-from-scratch Midwestern comfort food like a perfectly flaky chicken-and-biscuit pie ($12) served in a ceramic crock. The two-year-old neighborhood café is vegetarian-friendly—despite the meat-centric grub, in-house butcher, and trio of stuffed deer heads on a wall—with many dishes available in a vegan version using greens from urban farm Sweet Water Organics.
Take farm-to-table dining to the next level at Roots, where the menu showcases root vegetables harvested by chef-owner John Raymond at a plot he leases 25 minutes away (he also runs a hydroponic farm in the basement of his house). If weather permits, enjoy pre-dinner drinks on the patio overlooking the city and its namesake river, then order entrees like the maple-glazed veggies, served with cornbread and local leeks in a sweet potato purée ($20).
3. What to Do
Browse the storefronts along South Kinnickinnic Avenue (known as “KK” to locals) in the neighborhood of Bay View. Men’s hat shop The Brass Rooster just opened inside the Historic Avalon Theater and is stocked with high-quality porkpies, fedoras, flat caps, and bowlers that owner John McLaughlin will only part with if they look good on the customer. A few blocks away is Sparrow Collective (2224 S. Kinnickinnic Avenue, 414-747-9229), a two-year-old clothing shop/gallery showcasing handmade necklaces, beer soap, screen-printed tees, and other goodies by local designers.
Pass by classic “Cream City” brick buildings with beer baron names like Blatz, Pabst, and Schlitz on your way to Milwaukee Brewing Co. Opened in 2007, the 50-barrel craft brewery taps into the city’s history with suds like the Pull Chain Pail Ale, an ode to the days when workers had union-mandated beer breaks. Sign up for a tour ($7) on Friday evening, when home brewers stop by to talk shop with brewmaster (and CIA grad) Bert Morton and taste some of his herb-infused prototypes. End the night at Lakefront Brewery, which just released its seasonal pumpkin lager and serves up a traditional fish fry to the tune of the Brewhaus Polka Kings.
Catch burgeoning bands like alt-country duo Civil Wars (November 8; $18) at Turner Hall, the smallest (and newest) of three music venues operated by the nonprofit Pabst Theater Foundation inside historic buildings. Built as a social club for German-American gymnasts in 1882, the two-story ballroom resembles an East Berlin relic with its peeled walls and blackened ceiling from fires long ago. Order a PBR Tall Boy ($3) and plant yourself by the sweeping balcony upstairs, where the railing is engraved with names dating as far back as 1920.
4. Insider’s Tip
Wisconsin native Frank Lloyd Wright is best known in Milwaukee for the flying saucer–like Annunciation Greek Orthodox Church in the suburb of Wauwatosa, but get acquainted with some of his lesser-known work by visiting his American System-Built Homes. Designed as affordable homes for working-class families under the guise of “Democratic Architecture” between 1915 and 1916, six of the structures still stand on West Burnham Street, between 28th Street and Layton Boulevard. Though most of their geometric facades hide various states of deterioration, one 800-square-foot bungalow (2714 West Burnham Street) was restored by a nonprofit now offering tours (from $5) of its modest interior.
5. Oddball Day
Fuel up for a day of retro fun with a honey latte (from $3.25) and potato-bacon breakfast burrito ($5.45) at Alterra at the Lake. Drive less than ten minutes away to Riverview Antique Market and take your time perusing the booths of 50 dealers selling mostly 18th- through 20th-century folk art and furnishings, including a twenties chrome desk-lamp with attached ashtray ($75, booth #8). Then stop by Old World Third Street to see sausage emporium Usinger’s, which has been open since 1880, before having lunch at Leon’s Frozen Custard, a 1942 drive-in diner serving chili dogs ($1.96), homemade sodas (from $2.76), and custard ($1.20). Minutes away is Holler House (2042 W. Lincoln Avenue, 414-647-9284; $4 per game, plus pin-setter tips), the oldest sanctioned bowling alley in the country. With a little notice, 85-year-old owner Marcy Skowronski will hire a pin boy to work the two basement lanes, or you could just get a Miller shorty ($1.50) at the upstairs bar to hear her tell stories about the bras hanging from the ceiling. Afterward, head to Angelo’s Piano Lounge (1686 North Van Buren Street, 414-347-4144), where a jukebox playing Peggy Lee and Duke Ellington entertains when local performers aren’t reviving Rat Pack–era tunes on a dimly lit stage. Stay in the sixties by meeting your reservation at the supper club–style Five O’Clock Steakhouse. Orders are taken at the bar before you’re seated in a dining room decorated with year-round Christmas lights and mirrored walls. Get the perfectly buttery filet, done as a “kings cut” ($40) or daintier “ladies cut” ($28), and watch it appear shortly after you reach a table already dressed with salad, bread, and a relish tray.
Whether you’re looking for a good Packers bar or the best breakfasts spots, go to OnMilwaukee, a fine resource for all Brew Town has to offer.
See the city on two wheels by downloading maps from Go Milwaukee and riding along 95 miles of bike lanes.
The Journal Sentinel’s online entertainment calendar covers concerts, gallery openings, and film festivals.
Get the lay of Milwaukee’s premier warehouse district by visiting the Historic Third Ward.