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Alex Schechter
December 20, 2017

There’s a lot to love about Wisconsin’s largest city. For starters, two of television's most beloved sitcoms hail from here — "Happy Days" and "Laverne & Shirley" were both fictionally based in Milwaukee (in fact, Henry Winkler has a life-size statue in his honor, appropriately named the Bronze Fonz).

And this city has plenty of fun things to do for beer drinkers: Pabst Blue Ribbon was established here in the 1800s, and the legacy of the city’s original “beer barons” lives on today at places like Brewhouse Inn & Suites, Miller, and Lakefront Brewery.

Meanwhile, the city is laying a path for its future — a new 30-acre NBA arena is on the horizon, and 2018 marks the debut of Milwaukee’s first-ever streetcar transportation system, making it easier than ever to spend a vacation here.

Where is Milwaukee?

Set along beautiful Lake Michigan, this former manufacturing town in Wisconsin has easy access to sailing and windsurfing during the warmer months. In addition to the lakefront, a visit to Milwaukee always includes a scenic stroll along Milwaukee River, where a two-mile promenade is lined with public art. Milwaukee is an easy hour and a half drive from Chicago.

Courtesy of Visit Milwaukee

Milwaukee’s Top Attractions

Even if you only come to Milwaukee for the beer, the city’s unique museums and art venues are also compelling points of interest for travelers — not to mention the residents themselves. Zeroing in on Milwaukee’s easy-going, small-town vibe is a true pleasure.

“Everybody knows everybody here,” Theresa Nemetz, of Milwaukee Food Tours, told Travel + Leisure. “We’re all looking to see each other succeed.” In fact, as you weigh the options, it’s worth simply asking locals, who (like Nemetz) will jump at the chance to show off their wonderful city, offering suggestions on what to do in Milwaukee.   

A proper visit to Milwaukee should of course start at the Milwaukee Art Museum, which has become a symbol of the city’s sophisticated cultural cache — specifically, the Calatrava annex. Its dramatic, free-flying design was the first U.S. project for the famous Spanish architect, Santiago Calatrava. Inside the museum, there are more than 30,000 pieces including works by Picasso and Monet, as well as one of the largest Georgia O’Keeffe collections in the world.

Don’t let that serene lakefront setting fool you, though. Milwaukee is also home to one of the most rock ‘n roll exhibits in the Midwest: the Harley Davidson Museum. The 20-acre campus is set adjacent to downtown, and counts over 350 gleaming models in its artillery, plus an engine room that breaks down the mechanical parts into a visually stunning diorama.

For those looking to soak up the sights of Milwaukee’s skyline while appreciating good art, Wisconsin Avenue is the place to go. In 2017, the main thoroughfare began hosting Sculpture Milwaukee: an outdoor gallery featuring 22 sculptures by world-class artists like Sol LeWit and Alison Saar (plus a few Milwaukeeans). The installation, which ran from May through October, proved so successful that plans are already underway to make it a recurring annual event.

Best Beaches in Milwaukee

Tucked inside Lake Park is the gorgeous Bradford Beach, one of the top beaches in Milwaukee. Despite its close proximity to downtown, the beach is an oasis of golden sand and rippling blue waves. It even attracts a robust group of surfers. The beach comes alive during summer, when locals show up on weekends to sip tiki drinks at the bar and practice volleyball (these courts host national competitions, so expect to find yourself playing with pros).

Courtesy of Visit Milwaukee

Major Events and Festivals in Milwaukee 

If you’re planning a summer visit to Milwaukee, be sure to carve out time in your itinerary for the Wisconsin State Fair, which takes place each August. Little can compete with this jam-packed, 11-day blowout, which features live performers (comedians, dueling pianos, bodybuilders) on the main amphitheater stage. There’s also plenty to eat: from maple syrup-black pepper bacon to cherry pie, and every local delicacy you can imagine (Wisconsin cheese, sausage, classic maple syrup) all housed under one tent.

While Milwaukee makes no secret of its strong German heritage (each July, German Fest takes over central Marktplatz with German nibbles and an unmissable Dachshund Derby), other nationalities are given top billing here, too. Irish Fest (August) is the world’s largest Irish cultural festival outside of the Emerald Isle, while Festa Italiana (July) brings gondola rides, Italian opera music, and fireworks (not to mention a mouth-watering series of cooking demonstrations) to the 75-acre lakefront Henry W. Maier Park.

Shopping in Milwaukee

Just south of downtown Milwaukee, historic Third Ward is a veritable treasure trove for shoppers seeking all kinds of fun souvenirs. Sandwiched between I-794 and the Milwaukee River, the tiny neighborhood only spans 16 blocks. But that hasn’t stopped creative business owners from making it the number one retail destination for everything from lumberjack-style menswear (Milworks) to locally made jewelry (Lizzibeth) and hand-made leather handbags (Bursajo Boutique), alongside well-known brands like West Elm, Restoration Hardware, and Anthropologie. 

If you’re looking to do some heavy-duty shopping, drive 20 minutes west of downtown to get to Mayfair, one of the state’s biggest shopping centers. At this luxury mall, which borders the historic village of Wauwatosa, you’ll spend hours rummaging through the racks at Vans, Kate Spade, Eddie Bauer, and more than 150 other outlets, while also having access to a full movie theater with IMAX screens.

Courtesy of Visit Milwaukee

Milwaukee’s Best Restaurants

Restaurants in Milwaukee are something of a forte for Nemetz, whose tours — both walking tours as well as bus tours— offer a comprehensive (and delicious) look at Milwaukee’s most quintessential places to eat.

“People are coming up from Chicago just to check out our restaurants,” she told T+L, referencing new places like Red Light Ramen (only one item on the menu) as well as old-school joints like Caradaro Club (the first pizzeria ever licensed in the state of Wisconsin) and Leon’s, for traditional Milwaukee-style frozen custard in a classic 1950s drive-thru diner setting.

Most romantic restaurant: Sanford

Best cheap eats: Comet Cafe

Best seafood restaurant: Third Coast Provisions

Best burger joint: Crafty Cow

Best Spanish restaurant: Amilinda

Best pizza restaurant: Palermo’s Pizza

Best bakery: Treat

Courtesy of Visit Milwaukee

Best Bars in Milwaukee 

For a town with such a long history of booze-making, Milwaukee has seen unprecedented growth in the number of its local breweries and distilleries lately. One of the biggest beer-related events in 2017 was the reemergence of Pabst Brewing Company, which unveiled a new microbrewery on its former factory grounds in April.

Meanwhile, Milwaukeeans are big fans of the public beer garden, the newest one being Whitnall Park, which frequently hosts live music. Closer to the University of Wisconsin-Milwaukee campus, you’ll find Estabrook Beer Garden — a traditional Munich-style drinking spot with riverside views and access to Estabrook Park.

Visitors can also venture out at night to one of Milwaukee’s traditional Irish pubs, which usually offer an enticing mix of both local Wisconsin and imported Irish brews on draft. For a real history lesson, visit one of Milwaukee’s original “tied houses,” which breweries built in the 20th century to exclusively sell their product (many, like Regano’s Roman Coin, have been remade as bars and are still open).

For something more aligned with modern tastes, there’s Evolution, a hip gastropub with rooftop seating and a ping pong lounge. Over at Dock 18 in Walker’s Point, a craft bitters studio and a local distiller have joined forces to create a highbrow cocktail bar with regularly changing menus and staff-taught cocktail classes.

Easy Day Trips from Milwaukee

Compared to Chicago, whose lakefront skews more toward the development of condo towers and commercial buildings, Milwaukee has very little of that. Call it an homage to early citizens’ German socialist ways — the landscape in Milwaukee tends to cater to the people, rather than corporations.

For an easy getaway from downtown Milwaukee, head over to Milwaukee Kayak Company, where an afternoon spent kayaking on the river will set you back just $35 (per person). Begin your paddling adventure south of Third Ward, and head north, where you’ll dock at Lakefront Brewery, whose tour guides moonlight as improv comedians, promising plenty of laughs along the way.

Courtesy of Visit Milwaukee

Where to Stay in Milwaukee 

With much of Milwaukee centered around the charming lakefront, it’s easy to find a place to stay that offers great value as well as outstanding views. Several of Milwaukee’s best hotels play up the city’s history as one of America’s first beer capitals. And with good reason. After all, what better place for a decent nightcap than a vibrant bar located downstairs from your room?

Boutique Hotels

One of Milwaukee’s newest boutique hotels is the Kinn Guesthouse, which is run by the same family as Chicago’s famous Drake Hotel. Meet friends on the patio at the hotel restaurant, Kindred on KK, and share dishes like wild boar sliders and Wisconsin cheese plates keep guests toasty in the winter.

Other boutique options in downtown Milwaukee include Aloft Milwaukee Downtown and Kimpton Journeyman, which offers leather backpacks and bike rentals to all guests.

The fashionable Iron Horse Hotel, located just south of downtown, has taken over a century-old warehouse and established itself as a hub for Milwaukee’s cosmopolitan elite. The 100-room boutique hotel is not just pet-friendly — it’s motorcyclist-friendly, too.

Luxury Hotels

For one of the most attractive hotel bars in the city, head to Westin Milwaukee. The luxury hotel has impeccable lake views as well as Stella Van Buren, an Italian-influenced steakhouse with a menu by James Beard Award-nominee Andrew Ashmore.

Affordable Hotels

For something more affordable, try the Brewhouse Inn & Suites, whose lobby displays the original copper brewing kettles from Pabst Brewing Company. Residence Inn Milwaukee Downtown has rooms from under $150 a night, and its central location on Wisconsin Ave makes it the perfect lakefront hotel.

Vacation Rentals in Milwaukee 

If you need to find a place to stay with a little more local flavor, consider booking a home rental in one of Milwaukee’s historic neighborhoods on websites like Airbnb or HomeAway.

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