- Distance from Chicago: 93 miles
- Best time: May to October
- Best for: BudgetArts and CultureShopping
For anyone who was watching TV in the 1970s, Milwaukee will forever be associated with Happy Days and Laverne & Shirley, the BFFs who, fittingly, worked in a brewery. Indeed, beer still constitutes an important part of the city's fabric, but it has also morphed into a multi-faceted destination with world-class art and award-winning restaurants. Like Chicago, Milwaukee prides itself on its distinctive neighborhoods, the Historic Third Ward being one of the trendiest, with its renovated buildings used now as galleries, cafés, and boutiques. And when you're hankering for that Happy Days blast from the past, be sure to head to the Milwaukee Riverwalk for a photo-op with the Bronze Fonz sculpture. – By Elisa Drake
Milwaukee Cheat Sheet
View a printable list of all sights, restaurants, entertainment, and hotels from this itinerary. View
1Spend your first evening browsing through one of Milwaukee's hippest hoods. Listed on the National Register of Historic Places, Milwaukee's Historic Third Ward makes for a stellar shopping trip. Independently owned women's clothing shops and more than three dozen art galleries are housed in restored historic buildings. We hope you left some room in your luggage.
2Just a five-minute drive north on Milwaukee Street takes you to the East Side for dinner at the lovely Sanford Restaurant whose chef de cuisine Justin Aprahamian won the James Beard award for best chef in the Midwest in 2014. It's no wonder, too, considering the artistry that comes out of his kitchen in dishes such as grilled pear and Roquefort tart with caramelized onions and walnuts and grilled wild sturgeon on crab hash.
3It's a mile-and-a-half walk south on Water Street to your next stop. You're in Brew City, so it's only right that you should mark the trip with a beer. Hit the Milwaukee Ale House, where your hops come with history in the 100-year-old former saddle-making factory, right alongside the Milwaukee River in the hip Third Ward. Try a seasonal offering or a year-round brew, including their amber ale or stout.
Insider Tip Need some spa therapy? About an hour north is Kohler, Wisconsin, named for the local bath company. There's a design center and an elegant resort, but don't miss the ultra-pampering treatments at the heavenly Water Spa. A glass-enclosed rooftop deck features a co-ed whirlpool and fireplace, so remember your swimsuit.
1Power up for the day at Alterra at the Lake, a coffeehouse in an 1888 historic building by the river. Java here is freshly brewed, free-trade, and organic. The made-from-scratch pastries are a bonus.
2The can't-miss attraction is hands-down the Milwaukee Art Museum, featuring Santiago Calatrava's eye-popping Quadracci Pavilion that hosts temporary exhibits. Arrive by 10 a.m. to watch the opening of this modern addition's famous exterior "wings." With a span as wide as a 747, it's a breathtaking vision. The artwork inside doesn't disappoint either, boasting an impressive collection focusing on nineteenth- and twentieth-century American and European art. Pick up one of the self-guided themed tours or join a docent-led tour, held every Saturday at 11 a.m. and 2 p.m.
3Another iconic form in Milwaukee is The Domes of the Mitchell Park Horticultural Conservatory. The three 85-foot-high glass domes are photo-worthy themselves, and underneath, you'll find the natural beauty—in the tropical, arid, and seasonal plant and flower displays.
4Fat, juicy certified Black Angus beef burgers are what's in store at Sobelman's—they serve about 150 of them at lunch daily—though you can also order a Southwest chicken sandwich, fish sandwich, or black bean veggie burger. It's all good at this "rugged" biker-friendly joint.
5From lunch, head back about two miles east toward the river to learn some city history from a different perspective aboard the Milwaukee River Cruise Line's Historic Milwaukee Boat Tour. It's an hour and twenty minutes packed with information about its brewing and German heritage, industrial contributions, historical development, and local celebs.
6The next destination, just a five-minute drive west, proves a perfect complement for that beer history you heard about and adds a little culture and art: a guided tour of the Pabst Mansion. Completed in 1892 for beer baron Captain Frederick Pabst, this treasured landmark epitomizes Milwaukee's Gilded Age, decked out in high style with terra cotta ornamentation, painted and textured walls, and stained-glass windows.
7Hop on the farm-to-table bandwagon at Milwaukee's newest hot spot Braise. Owner and well-known Milwaukee chef Dave Swanson has said his motto is "reconnecting with our food." At his innovative community-supported restaurant, the menu changes daily depending on the fresh ingredients he gets from any of the 400 farmers he works with throughout the state. The result? Tantalizing dishes such as crispy pork belly and creamy polenta and mushroom and leek lasagna with Parmesan bechemela.
1The Historic Third Ward, Milwaukee's arts and fashion district, is filled with galleries and boutiques in high-ceiling warehouses. At the center of it all is Cafe Benelux, a casual, hip spot for brunch with a fantastic roof deck. Locals rave about the elaborate Bloody Marys, pannenkoeken crepes, and salmon Benedict.
2You don't have to own a Harley to appreciate its colorful past and super-cool style. A visit to the Harley-Davidson Museum is in order for any Milwaukee guest. Don't own a hog of your own? Try one on for size in the "Experience Gallery" for a virtual ride. Get a glimpse of the Serial 1 bike to see where it all started and make a stop at the Custom exhibit where you'll find the Elvis Bike and the mega-sized King Kong.
3You're in dairy land and it's practically an obligation to get some cheese or ice cream before you leave—we say get both. So head to the Clock Shadow Creamery, housed in the appropriately green FIX building, designed to be net-zero energy and carbon neutral. Here, you'll see cheese-making in progress. Take home some cheese curds, mozzarella, and other dairy products all made from rBGH-free local milk. The adjacent Purple Door Ice Cream gives you free reign to enjoy a scoop of small-batch homemade green tea, balsamic strawberry, or even whiskey-flavored ice cream.
Where to Stay
One of the Historic Hotels of the World, the Pfister Hotel (rooms from $159/night) is a great match for an arts and culture escape, beginning with its majestic, barrel-vaulted lobby and Victorian décor that reflect its 1893 heritage and continuing to its mini museum's worth of art. With more than eighty works on display, the Pfister houses the largest collection of Victorian-style art of any hotel in the world.
At County Clare (rooms from $140/night), the feeling is more intimate and homey, with twenty-nine rooms comprising the guest house, all with double whirlpool baths and pillow-top mattresses. Grab a pint of Guinness in the downstairs pub before tucking in.
When to Go
One of the great things about Milwaukee is its dual river and lake shorelines, making for scenic strolls, meals with views, and plenty of waterway recreation. The city thrives in warm months when summer festivals are in full swing and the outdoor beer gardens are overflowing. On the flip side, the city gets a little sleepier in the winter months when there's a biting chill off Lake Michigan, but there's still plenty to do indoors with museums, holiday festivities, and vacation packages at hotels.
If you plan your trip around Summerfest (late June to early July), you'll have to book your hotel stay early because you'll be in the thick of what's considered the world's largest music festival. The main stage, plus ten others, feature headliners and a host of up-and-comers.
How to Get There
By car: Time your drive right, and you'll fly to Milwaukee in an hour and a half. Just go straight north on I-90/94, continuing on US 41 North when it splits. If you're traveling at rush hour, factor in another twenty minutes or so. Once you get there, public parking lots abound, and rates are a fraction of what Chicago charges.
By train: The Hiawatha Amtrak line runs seven roundtrips (six on Sunday) from Chicago's Union Station to Milwaukee's Intermodal Station, which is downtown within a short walk of several hotels and a quick taxi ride to other destinations. You'll avoid traffic and can count on a simple 90-minute ride.
Car Rental Deals
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