While Milwaukee is known for its heritage of beer, cheese, and extremely loyal sports fans, it is also a proud and neighborly city that seamlessly blends history, culture, and vibrant experiences. Modern-day Milwaukee remains unpretentious, but it is quite a departure from Hollywood’s portrayal of the city during the television sitcoms of the 1970s, Happy Days and Laverne & Shirley. This cosmopolitan, hip, and ethnically-diverse destination is welcoming to all people. Over time, Milwaukee has become a hub for the arts, sports, and gastronomy. I’ve always believed that recommendations from locals are key when visiting any city. During a chat with a Milwaukee ride-share driver named Lonnie on my first day exploring, he made a remark that stuck with me, “Los Angeles and New York City are akin to fine dining, but Milwaukee is a home-cooked meal!” Within a short span of time, it was clear that Lonnie was correct. This is how UPTOWN recommends you experience “the good land.”

Hilton Milwaukee City Center and Pfister Hotel

After checking in for your stay at the historic Hilton Milwaukee City Center or the Pfister Hotel, which serves an amazing daily breakfast, start your experience in Milwaukee right. Book City Tours MKE‘s roughly two-hour Iconic Milwaukee Tour to discover the city’s rich heritage and iconic landmarks. This tour, which takes place aboard eco-friendly cruisers or buses for larger groups, takes you through the Lakefront. You can snap a photo with the “Bronze Fonz,” a height-accurate sculpture of Happy Days actor Henry Winkler who iconically portrayed “The Fonz” in the series. The tour also takes visitors through Milwaukee’s stunning architecture, Brewery District, and many more haunts!

For food lovers, the 3rd Street Market Hall is a must. With its TopGolf Swing Suite, this unique food hall offers numerous gastronomic offerings, some of which exhibit strong culinary award potential. Outlets like Pho Spot MKE, which serves authentic Vietnamese fare; Criollo which fuses Latin American with Caribbean Creole cuisine; and Smokin’ Jacks BBQ are standouts at this bustling culinary hub. 

Milwaukee Public Market

The Milwaukee Public Market is a hub for delectable food and more.

Another location for great eats and more is Milwaukee Public Market. Located in the historic Third Ward, which is known locally as the city’s arts and fashion district, Milwaukee Public Market offers an upscale experience that’s very relaxed and accessible. One of the most popular eateries is Thai-namite, which offers very authentic Thai curries and traditional dishes, including Pad Thai and Pad See Ew. While here, you should also enjoy some of the locally roasted and brewed coffee offerings at Anodyne Coffee Roasting Company. Speaking of java …  coffee aficionados will also appreciate the local artisanal brews of Colectivo Coffee and Discourse Coffee, which are located throughout Milwaukee.

Chef Dwight Jackson’s Pepperpot

A visit to Milwaukee isn’t complete unless you visit Chef Dwight Jackson’s Pepperpot Jamaican Restaurant!

One restaurant that you cannot pass up when visiting Milwaukee is Pepperpot. This restaurant specializes in authentic Jamaican cuisine, which is some of the best outside of Jamaica. Chef Dwight Jackson, a native Jamaican, opened this restaurant within Milwaukee’s Bronzeville district in 2013, and the chef’s bold flavors struck quite a chord with the community. Within the first 48 hours of my stay, five locals told me that I must visit Pepperpot – it’s just that popular! I can attest, you will be quite satisfied with Chef Dwight’s culinary genius. Start with his popular Jerk Chicken Egg Rolls, as well as, the Salt Fish Fritters; add-on the Chicken Rasta Pasta as your entrée; and order a cold glass bottle of the authentic Jamaican soft drink Ting for your beverage. I couldn’t pass up the opportunity to guzzle a bottle of Ting because the authentic Jamaican version is very hard to find in the US and I have been missing it. However, let me be very clear, Pepperpot has extensive cocktail and wine selections, so you if you’re jonesing for a rum punch, a Jamaica Mama, or even a glass of Black Girl Magic Wine, you will be satisfied. Interesting fact, Chef Dwight’s father led a large demonstration in Jamaica in response to the assassination of Dr. Martin Luther King in 1968. Truly, the irony of Pepperpot’s location being on Dr. MLK Jr. Drive is not lost on Chef Dwight.

After a great meal at Pepperpot, you should spend some time perusing Bronzeville Collective MKE. This store provides small brands a platform to offer their products in a collaborative community-centric space. Whether you’re seeking apparel, bath and body products, jewelry, or home items, Bronzeville Collective is a must because your local pickups can serve as souvenirs of your Milwaukee visit.

America’s Black Holocaust Museum in Milwaukee

A visit to the poignant, America’s Black Holocaust Museum is recommended for every person visiting Milwaukee for the first time.

The America’s Black Holocaust Museum, which chronicles the poignant history of African-American life starting with the transatlantic slave trade in raw detail, is also located in the Bronzeville area. This museum highlights the stunning insights surrounding America’s very messy racist history and it doesn’t hold back with its depictions surrounding the inhumanity of slavery, ethnic inequality, and the struggles of Black Americans doing their best to persevere against considerable odds. America’s Black Holocaust Museum does more than shock, though, it provides the facts of American history that are desperately needed at a time when elected officials throughout the US are committing an appalling injustice, in an attempt to change the narrative and prevent America’s youth from knowing the realities of this nation’s heritage. To keep such uncomfortable truths hidden only serves to embrace ignorance and perpetuate further injustices. And let’s be real, the Holy Bible is one of the rawest publications on the planet, but some of those same “God-fearing” politicians who want to rewrite American history are curiously silent when it comes to children having access to the grisly, morbid, and sexual descriptives that are found throughout Holy writ. Food for thought.

Shifting gears … 

Explore the quirky side of Milwaukee at the National Bobblehead Hall of Fame and Museum. Where you can marvel at the vast collection of Bobbleheads and learn about their fascinating history. Art enthusiasts will be captivated by the Milwaukee Art Museum’s stunning architecture and diverse collection of artworks. Another museum that is a must when in Milwaukee, especially for motorcycle enthusiasts, is the Harley-Davidson Museum. Currently 15-years-old, this museum contains more than 450 Harley-Davidson motorcycles and hundreds of thousands of artifacts from the company’s 120-year history.

Culture X Design’s Sneaker & Streetwear Summit

Culture X Design’s Sneaker & Streetwear Summit includes exhibits and shopping opportunities from Marie Carter’s Classic Shoppe (pictured left) and MAWDoods’ SHOEBOXSERIES (pictured right).

When it comes to events, Milwaukee is always abuzz! From professional sports with Milwaukee Brewers baseball, Milwaukee Bucks basketball, and Milwaukee Admirals ice hockey; to live performances within its historic theaters; to the yearly Battle of The Chefs, which is a thrilling culinary competition showcasing the talents of Milwaukee’s top chefs, there’s something for everyone to enjoy! For example, Culture X Design’s Sneaker & Streetwear Summit attracts individuals with a passion for streetwear. You can explore the latest trends and connect with like-minded individuals, including Wisconsinites Marie Carter, owner of The Classic Shoppe, as well as Mitch Wachtendock, the self-proclaimed sneakerhead and artist of the SHOEBOXSERIES who is also known as MAWdoods. Carter, Wachtendock, and many other local vendors represent Wisconsin well with their creative and quality-minded approach to fashion and the arts.

Whether you’re a history buff, foodie, art lover, or sports fan, Milwaukee offers something for everyone. Come and experience the warmth and hospitality of this incredible city!