Why is Everyone Surprised by How Cool Milwaukee Is?

This is the latest in our series on underrated destinations, It’s Still a Big World.

In the ’70s, Milwaukee was known for the upbeat TV shows Laverne and Shirley and Happy Days; in fact, the “Bronze Fonz” statue that gleams over the Milwaukee River is a persistent reminder of what some consider to be the city’s glory days. In the ’80s, Jeffrey Dahmer took over as the city’s (very!) unfortunate claim to fame and, at one point, when I’d tell people I’m from Milwaukee, their first reaction would be “Oh, that’s where Jeffery Dahmer is from!” Indeed, it is.

For a while, we Wisconsinites didn’t have a lot going for us on the national stage so when a film about the cannibalistic “Milwaukee Monster” was screened in Manhattan a few years ago, just a few miles from where I lived at the time, I couldn’t help but feel a little bit excited that my hometown would be on the big screen. Is that weird? Please don’t answer that.

Times have changed. In recent years, when I tell others that I’m from Milwaukee, I’m surprised by how many respond by saying they had recently visited. Virtually all of them tell me they loved the city and I can tell by the shock in their voices that every single one of them was surprised they had such a great time. What did they expect from the land of beer and cheese? Actually, they probably expected little more than fantastic beer and cheese (which they surely found) but were then blown away by everything else the city has to offer – and how cheap it is.

Milwaukee is a great city to wander around and get lost in alone but if you’d like some guidance, check out Milwaukee City Tours, which feature history, culture, and food tours around the city (most of the food tours will resume in May, 2021).

Arts and Culture

Given its population is just over 600,000, many would be surprised that Milwaukee can sustain a symphony orchestra, an opera, and a vibrant theater culture. As the birthplace of Harley Davidson motorcycles, it’s no shock that the city has a Harley Davidson Museum. What fewer out-of-towners know is that the city will soon also be the home of America’s Black Holocaust Museum, which will re-open its doors later this year after closing in 2008.

The Milwaukee Art Museum is reason enough to visit the city. The strikingly modern structure completes the downtown skyline, peering out onto Lake Michigan and opening (then closing) its retractable “wings” each morning and evening. Its designer, Santiago Calatrava, went on to design the famed World Trade Center Oculus in lower Manhattan; I take great pride in pointing out to my fellow New Yorker that the building is beautiful, but it also looks like a rip off of Milwaukee’s Art Museum. The museum has become so ingrained into the identity of the city that its silhouette serves as the logo of the Visit Milwaukee tourism site and appears on welcome signs at the city’s General Mitchell International Airport.

Each summer, Milwaukee hosts (depending on who you ask) the world’s largest outdoor music festival, Summerfest, where about $20 will give you access to a full-day of live performances by local and national acts like Jason Mraz, Jimmy Eat World, Chaka Khan, Rodrigo y Gabriela, The Roots, Hanson, Ludacris, Foreigner, and Third Eye Blind. For an additional cost, you can get a ticket to shows in the ground’s amphitheater to see even bigger acts. 2019 performers included Willie Nelson, Lionel Richie, The Killers, Jennifer Lopez, Lil Wayne, and Snoop Dogg, just to give you an idea of the festival’s musical diversity. After the 10-day mid-summer festival, the sprawling, waterfront fairgrounds host cultural festivals through the fall that celebrate the diversity of the city: German Fest, Festa Italiana, Mexican Fiesta, Irish Fest, PrideFest, Black Arts Fest MKE, etc.

Food and Drink

I’m not going to pretend that Milwaukee isn’t known for its beer and cheese or that its massive German population hasn’t made it a great place to find traditional German fare. You should know, however, that Milwaukee is an extremely diverse city so limiting yourself to any preconceived notions about its food would be a mistake. Yes, you should visit some of the city’s best German restaurants and beer halls on Old World Third Street. While you’re downtown, pick up some sausage at Usinger’s, where it’s been made for 140 years. You should also visit Alem Ethiopian restaurant (also downtown), which happens to be my favorite restaurant in the city. Shout out to their killer vegetarian lunch buffet!

For non-Ethiopian meals, my favorite place to eat in the city (and to purchase hard-to-find cheeses for my dairy-starved friends in New York City) is the Milwaukee Public Market. Have your pick of Thai, Mexican, Italian, seafood, or vegan fusion, then wash it down with a craft beer or one of Milwaukee’s signature over-the-top Bloody Marys, topped, of course, with sausage sliders and fried cheese curds.

Personally, I can’t wait for the new 3rd Street Market Hall to open this spring. The food hall occupies a former shopping mall where I worked at Foot Locker as a teenager and it’s being redeveloped into a huge food hall with a beer garden and gaming area (think giant Jenga, virtual golf, and original console video games).

Outdoors and Nature

Milwaukee is kind of like a small Chicago (which is a quick 90-minute drive south) in that it borders Lake Michigan and has beautiful rivers flowing throughout the city. The downtown Riverwalk area is charming any time of year but in the summertime, you can also kayak or paddleboard in the river or watch lively boat parades. Wisconsinites are known to be friendly and if you’re lucky enough to make friends with someone with a boat, ask them to take you to one of the riverfront bars that will serve you right in the boat. Then please send me their number so I can ask them to take me for a boat ride next time I visit.

For urban exploring in Brew City, grab a Bublr bike share bike, named after the everyday drinking fountains that Wisconsinites affectionately call “bubblers”. The East Side, downtown, and Bay View neighborhoods are great to explore by Bublr or you could rent a proper bike and jump on one of the city’s nature trails. Cycling enthusiasts should rent a proper bike (and a car) and head to one of the state’s 101 rail trails (former railroads converted into cycling and pedestrian paths). Two good options would be the Glacial Drumlin State Trail and the Elroy-Sparta State Trail, which, when established in 1965, became the country’s first multi-use recreational trail.

If you want to stay within the city but feel like you’re in the forest, head to the Milwaukee suburb of Cudahy, named after the Irish immigrant meatpacker, Patrick Cudahy, who established a pork processing plant that still causes much of the southern suburb to smell like bacon. Seven Bridges Trail, located in Cudahy’s Grant Park, borders Lake Michigan, has its own stretch of beach, and its dense foliage, rustic trails, and meandering streams make it feel like you’re deep in the woods. Should you want to visit an actual forest, Kettle Moraine State Forest (40 minutes north of Milwaukee) is great for both summer and winter hiking.

Technically, camping is also a year-round activity (and I’ve had great experiences snow camping during the Wisconsin winter), but unless you’re really into the outdoors, I’d leave camping for warm weather months.

Daytrips from Milwaukee

There’s plenty to do in Milwaukee to keep you busy but if you want to check out a few nearby cities and attractions, here are my top picks:

Madison

The state capital and college town of Madison has loads of nature opportunities within the city, like the Lower Yahara River Trail and floating boardwalk, and the 1,200-acre Arboretum and its 17 miles of trails. The city (about 90 minutes west of Milwaukee) is also in close proximity to some of the most beautiful stretches of the 1200-mile Ice Age hiking trail.

Spring Green

Two hours west of Milwaukee (about 45 minutes past Madison) is the village of Spring Green, best known for the American Players Theatre. The renowned outdoor theater features the region’s best Shakespearean performances – aim to get there early so you have time to walk around the prairie and picnic on the grounds. One mile from the theater is Taliesin, the 800-acre former estate of Frank Lloyd Wright. In May, 2021, tours will resume of this National Historic Landmark and UNESCO World Heritage Site.

Horicon Marsh

More than 33,000 acres large, Horicon Marsh is the largest freshwater marsh in the US (it’s also said to be the largest freshwater cattail marsh in the country). If you’re into birds, this is the place to be. My dad was a nature-loving hippie so he took my sister and me here to watch thousands of migrating birds each fall. Though autumn is the best time see migratory birds, the wildlife area is home to dozens of bird species year-round and offers hiking, kayaking, canoeing, and educational programs to the public.

Sheboygan

Sheboygan, about an hour north of Milwaukee, is the freshwater surfing capital of the world. Yes, you read that right. Freshwater surfing is really a thing and they even do it during the freezing cold winter. I find it entertaining to just sit and watch surfers but if you want to actually do something, you could take a surfing lesson on the beach, or go kayaking, biking, hiking, or stand up paddle boarding in nearby state parks.

Cassandra Brooklyn is a writer, travel expert, and group tour leader. She runs EscapingNY, an off-the-beaten-path travel company, and is the author of the guidebook Cuba by Bike.