The Iron Horse Hotel
500 W. Florida St., Walker's Point
A warehouse-turned-hotel, the Iron Horse has a hundred loft-like rooms—some with city views and others overlooking “The Yard,” the Iron Horse’s outdoor patio and lounge. The “premium” version of the loft is on the top floor, with twelve-foot ceilings, and showcases the building’s charming exposed brick walls and industrial beams. (The other prime room to request is the corner alcove king.) For a good hotel option in the third ward, we like Kimpton’s new Journeyman, which is unique enough to feel like it’s independently owned.
550 N. Harbor Dr., East Town
Brothers Joe and Paul Bartolotta—who grew up in nearby Wauwatosa, Wisconsin—opened their first Italian restaurant together in 1993. Harbor House is their take on a New England seafood place (fresh fish is flown in from both coasts), set on Lake Michigan with views of the Milwaukee Art Museum and downtown. Oysters are their big thing and their happy hour (4pm-6pm on weekdays) is hard to beat.
Leon’s Frozen Custard
3131 S. 27th St., Southgate
Locals can argue about the best custard in town but Leon’s is undeniably a staple of the city—and really good. Open year-round (and run by the same family since 1942), they also do burgers, hot dogs, and old fashioned sodas, with the custard sundaes being the clear winners.
Milwaukee Public Market
400 N. Water St., Historic Third Ward
Located in the Historic Third Ward section of Milwaukee—its oldest center of commerce/warehousing, which was rebuilt after a devastating 1892 fire—the Public Market is a hub of local and specialty food vendors. In addition to the to-go market items, you can stop here for a meal (there’s seating on the second floor in their Palm Garden), and cooking classes are on offer, too, which you can sign up for here.
2999 N. Humboldt Blvd., Riverwest
In the past twenty-five years, this indie coffee operation has grown to a dozen-plus cafes in Milwaukee (and a few in Madison), which makes it all the easier to get a good brew in the city. Colectivo takes their sourcing seriously (beans come from Colombia, Nicaragua, Ethiopia, Guatemala, and more) and they roast everything in-house in Milwaukee; you can see them in action if you hang at the Humboldt Boulevard café in Riverwest, which is attached to the roasting facility.
Milwaukee Art Museum
700 N. Art Museum Dr., East Town
We couldn’t put together any sort of Milwaukee itinerary without mentioning the Art Museum, which has works dating back to the fifteenth century into the present-day. The Georgia O’Keefe collection here is one of the largest (O’Keefe grew up in Wisconsin). The Quadracci Pavilion, which was added to the museum in 2001 is a stunning 142,050-square-foot design by Santiago Calatrava that is simultaneously reminiscent of a grand Gothic cathedral and an imposing ship. Its “wings” close and open in response to changes in wind speed, which is very cool to watch. Art buff or not, this is simply a beautiful place to spend an afternoon. (Even the parking garage—a frequent site of car commercials—is ridiculously pleasant.)
Milwaukee Public Museum
800 W. Wells St., East Town
MPM (est. 1882) is home to four million specimens; collection highlights include: the most complete mammoth skeleton, rare butterflies, an upper-floor herbarium, plus pieces of Milwaukee’s history, like photographs taken by museum anthropologists who were working among Wisconsin Indian tribes in the 1900s. It’s kid- and adult-friendly—if you have littles in tow, though, check out the planetarium’s line-up of 3-D shows while you’re there.
144 E. Wells St., East Town
One of the oldest active theaters in the country, the Pabst was designed in 1895. The grand European-style opera house has undergone three major rounds of renovations/restorations and has remarkably stayed true to its original baroque look (with updates, of course). Today, it hosts around 150 music, dance, and theater performances annually.
Schlitz Audubon Nature Center
1111 E. Brown Deer Rd., River Hills
In the 1800’s, Nine Mile Farm—located nine miles from the Schlitz Brewery—was used as a resting spot for the Schlitz draft horses. In the 1970’s it became home to the Schlitz Audubon Nature Center, 185 acres with six miles of trails that winds from forest to wetland to bluff to views of Lake Michigan. The center, which is near a migratory flyway, has particular appeal for birders. There’s also regular programming geared towards kids, and in the winter, you can snowshoe/cross country ski on the trails.
Frank Lloyd Wright’s American System-Built Homes
2700 W. Burnham St., Burnham Park
One of the most interesting glimpses into Frank Lloyd Wright’s work can be caught from the 2700 block of West Burnham Street in Milwaukee. Here, there are several duplexes and bungalows from circa 1915 made with pre-cut factory lumber, designed by Wright with affordability in mind, and built by Arthur Richards, which are now known as the American System-Built Homes. This stretch of rare prefabs makes the best stroll in town.