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The Ultimate Wisconsin Road Trip Itinerary: Cheese, Craft Beer, and Hidden Gems

Kayaking along sea caves at Apostle Islands in Bayfield, Wisconsin.
(Travel Wisconsin)
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Awesome cheese, amazing beer and lots of things you never expected

Last summer, I drove more than 500 miles across Wisconsin, all the way from Milwaukee to Lake Superior, and during that journey I discovered two things.

First, all the cliches you’ve heard about the Badger State are true. The cheese really is out of this world (and cheese curds quickly became my favorite road trip snack food). Despite the demise of the old-time breweries like Pabst and Schlitz, the beer scene is alive and thriving, especially new craft breweries. The world’s most famous motorcycle brand was born in Milwaukee when friends William Harley and Arthur Davidson had this crazy idea to strap an engine to a bicycle.

The "Bronze Fonz" located on the Milwaukee RiverWalk
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But along the way there were also lots of surprises, especially for someone who had never been there before. Wisconsin is wicked beautiful, especially the many lakeshores and the northern woods. The big cities are surprisingly sophisticated, especially the food and art scenes. It’s one of the most bike friendly places I’ve ever pedaled. And the state boasts one of the nation’s best long-distance trails (especially for people who don’t like hiking uphill).

My journey kicked off in Milwaukee on (believe it or not) a dark and stormy night. But that’s the last rain I would see for days. And who needs to be out in the wet rain when sampling local craft brews at your hotel bar is followed by an amazing Italian gourmet dinner at Bacchus (the pork bolognaise is to die for).

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Inside the dining area of Bacchus in Milwaukee

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Dinner at Bacchus in Milwaukee

1. Inside look at Bacchus in Milwaukee 2. Soy-glazed salmon with ginger basmati rice, seaweed salad, smoked shoyu fumet 3. Main dining room at Bacchus 4. Niman ranch pork cutlet

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By the following morning the storm had hauled off across Lake Michigan and I was poised in front of the Milwaukee Art Museum with scores of other folks to watch its giant Metallic brise-soleil wings unfold at 10 a.m. The museum is especially known for its Georgia O’Keeffe collection (did you know she was born in Wisconsin?) and the headliner exhibition showcased the Spanish masters. But the collection that blew me away was the folk and self-taught gallery on the top floor, a tribute to natural born genius by artists who felt compelled to create even if they never made a dime from their efforts.

Milwaukee Art Museum on Lake Michigan

I don’t know about you, but I really work up an appetite (and thirst) exploring a cool museum. So my next stop was the restaurant at Lakefront Brewery, where an amber lager and beer-poached bratwurst – served with cheese curds (of course) did the trick.

Even though I normally avoid winery, brewery or distillery tours (they’re typically kind of boring), someone had told me the Lakefront Brewery tour was the best ever. And it really was awesome. Sure, there were facts and figures about the brewing process, but also lots of jokes and interesting things about Milwaukee that have nothing to do with beer. The tour ends on a literal high note when everyone is asked to sing the theme song from Laverne & Shirley (the vintage sitcom set in a Milwaukee brewery).

Lakefront Brewery in Milwaukee, WI
Outside Lakefront Brewery in Milwaukee, WI

It’s around a 90-minute drive from Milwaukee to Madison, the state capital and one of America’s legendary college towns. During a tour of the massive Wisconsin State Capitol, I was on the lookout for the 300-plus badger statues and images that grace the inside of the building, as well as numerous fossils that are embedded in the stairs and floors. There’s also Old Abe, a bald eagle that served as a mascot of Wisconsin troops during the Civil War.

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As a college town and very progressive urban area, Madison has created an extensive network of bike paths. And you don’t need to bring your own. You can easily rent one with just a credit card from more than 100 Madison BCycle stations scattered around town. Right outside my hotel, the multiuse Capital City Trail took me along the shore of Lake Monona and a railroad corridor to lush Olbrich Botanical Gardens. Adjacent to the greenery, the Dane County Farmers’ Market was in full swing around the Garver Feed Mill, a restored factory building that now shelters artisan food makers and plant vendors.

As a lifelong fan of Frank Lloyd Wright architecture, I made a pilgrimage to Taliesin, his legendary home and studio about an hour’s drive west of Madison. Escorting my little group through the main house, the guide offered detailed descriptions of the interior design and artworks, as well as the sordid details of life at Taliesin, including Wright’s scandalous love life and the 1914 mass murder and arson attack by a disgruntled former employee.

Frank Lloyd Wright Visitor Center

Another adventure on my Wisconsin bucket list was hiking part of the Ice Age National Scenic Trail. Jointly administered by the state and the National Park Service, it’s one of 11 national scenic trails along with more familiar routes like the Appalachian and Pacific Crest. The trail takes its name from the fact that it follows the outer edge of the last glacier icecap that covered much of Wisconsin around 11,000 years ago.

The Ice Age rambles roughly 1,200 miles between St. Croix Falls on the Wisconsin-Minnesota border and the Door Peninsula near Green Bay. There was no way I could hike the entire route (thru hikes take two to three months). But I could pick off a section here and there as I moved up the center of the state.

Ice Age Trail in West Bend, Washington County
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While hiking the Plover River Segment through deep woods I came across a guy with a lanky frame and long white beard. Clad in camo fatigues with binoculars pressed to his eyes, he said, “That’s sounds like a warbler,” and raised his camera to snap a photo.

I did a double take, thinking to myself this guy could easily be the ghost of John Muir. Because it was the woods and wetlands of central Wisconsin that the famed conservationist first became obsessed with nature during hikes away from the family farm. Those woodsy walks inspired him to undertake his epic “Thousand Mile Walk to the Gulf” and a lifelong passion for the outdoors that would eventually lead him to California.

Stevens Point seemed the most likely spot to break the drive after my day of hikes. It’s not a famous city by any means, but it does have its small-town charms. Like Fish Friday, another age-old Wisconsin tradition that traces its roots to the state’s fresh catch from two Great Lakes and the now much-less-followed rule that Catholics couldn’t eat meat on Fridays.

Asking around, I was told that a bar called Guu’s On Main did Fish Friday… batter than anyone else (pun intended). Despite the place looking like a biker bar from the outside, the menu is actually quite sophisticated – tequila lime shrimp, perch hoagies and ahi wonton nachos among its offers. But I went the traditional route, a platter of deep-fried cod fish with coleslaw, kettle chips and tartar sauce, and I wasn’t disappointed.

Stevens Point has its other charms. Like a Nordic Sauna Night, which I skipped because it seemed like a singles meet-up at which I would definitely be a fish out of water. And the Starry Night Cat Caf., which I visited out of an admiration for both Van Gogh and feline companions.

The following day I launched into the longest leg of my journey across Wisconsin, a four-hour drive through the North Woods to Bayfield on the shore of Lake Superior. I was booked into a place called the St. James Social, opened in 1884 as the town’s first hotel and recently refurbished into a cute boutique with a restaurant and bar on the ground floor.

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St. James Social

The lakeshore is right down the road, fishing boats moored to the piers and a small terminal for the vehicle ferry that chugs over to Madeline Island. But I opted for a different way to get out on the lake, a half-day kayak trip with a young Ojibwe guide from the Red Cliff Reservation.

Setting off from a remote cove near Bayfield, we navigated the calm waters between the lakefront reservation and Apostle Islands National Lakeshore, flitting through sea caves and beneath sea arches, and hovering over the wreck of the SS Fedora, a massive bulk carrier that sank in 1901.

Kayaking near Sand Island Lighthouse in the Apostle Islands Lake Superior

As we paddled back to Bayfield, there wasn’t another boat on the water, not a manmade thing in sight. A couple of bald eagles overhead and an aroma of North Woods trees drifting from the shore – may be only 500 miles from Milwaukee, but a whole different Wisconsin.

Apostle Islands Kayaking
(Travel Wisconsin)
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Travel by LA Times Studios

From quick escapes to dream adventures, we’ll share top destinations, tips, and experiences to inspire your next trip.

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