7 Wisconsin Area Road Trips

Find fun without driving across the country
whistling straits golf course
Whistling Straits golf courses north of Sheboygan

Eau Claire: Nightlife and Wildlife

There’s some irony in musician Justin Vernon seeking isolation in his father’s hunting shack north of Eau Claire to record “For Emma, Forever Ago,” Bon Iver’s 2007 breakout debut album, resulting in the west-central Wisconsin city gaining unprecedented attention. Vernon’s eclectic music festival Eaux Claires–in its third annual iteration this June 16 and 17–and his ongoing commitment to the town where he went to high school and college has created something of a renaissance there.

Despite the lure of music scenes in larger cities on either coast, Vernon has deliberately stayed in Eau Claire, built his April Base recording studio on the outskirts and invested in the boutique hotel and adjacent bar/restaurant–the Oxbow Hotel and the Lakely, respectively–all of which has brought a new cache to downtown. 7 Wisconsin Area Road Trips

Don’t expect to find a vacancy at the Oxbow during the music festival. But that may be the point. Taking in the 30-room hotel, restaurant and performance space–complete with a vinyl record library and bikes and kayaks available for free to guests–requires visiting on another weekend.

From there, it’s easy to navigate the city on foot as it straddles and showcases the Chippewa River. Downtown Eau Claire supports live music (check out the Acoustic Cafe most evenings), sculptors (whose lively and varied work is on display on a rotating basis) and a thriving farmers market, held June 1 through Oct. 29.

Eau Claire begs to be explored by bike as well. A place to start? The paved Chippewa River State Trail, which you must buy an annual or single-day pass to use, leads University of Wisconsin-Eau Claire students from their classes to hip coffee shops and back again. For mountain biking, head to the 120-acre Northwest Park, where most of the nine miles of trail is squirrely fun singletrack.7 Wisconsin Area Road Trips

After you’ve worked up a thirst, a hunger and a desire to sit still for a spell, a brew pub will meet all those needs. Back downtown you can choose between the Lazy Monk Brewing Bier Hall, The Brewing Projekt Taproom or, en route to the Lowes Creek County Park (home to more great trails), the “tasting lounge” of the Infinity Beverages Winery & Distillery.

By all means, go to Eau Claire for the music and libations. But be sure to return for the outdoor adventure, scenery and homegrown artistry to be enjoyed there. [JP]

Viroqua: Driftless Destination

Something is taking root in Viroqua, Wisconsin, which is situated in Vernon County, an area with the highest concentration of organic farms in any county in the United States. According to Luke Zahm, the local farmers are growing some of the best food in the world. “And I’ll go toe-to-toe with anyone who says otherwise,” he says.

The sprawling driftless region, an area skirted by the most recent passage of glaciers, not only offers panoramic views, but also an origin for unparalleled freshness in the bounty of food it produces. This is why Zahm does what he does at Driftless Cafe in Viroqua. He sources most of his in-season-only ingredients from a 50-mile radius, while also using the creative techniques he’s acquired over years of cooking (which include stints at Lombardino’s and Epic Systems). This is Zahm’s way of offering a unified glimpse into all that Viroqua has to offer. In this endeavor, Zahm has been named a James Beard semifinalist for Best Chef-Midwest, moving Viroqua to the top of many travelers’ road trip lists.7 Wisconsin Area Road Trips

While Driftless Cafe is a must-stop on this road trip, Zahm, also the Viroqua Chamber of Commerce president, is quick to identify the many other wonderful things you’ll find in Viroqua.

Sip coffee on Main Street at Kickapoo Coffee’s new Viroqua Cafe (the organic, artisan coffee roasters’ headquarters is on the north side of town) and grab a pastry at Cowboy David’s Coffee & Bake Shoppe. Once a pop-up business made possible by a Viroqua program, Cowboy David’s is now a permanent fixture and sweet tooth fix in Viroqua’s charming downtown. Peruse Main Street’s kitschy shops, including Gary’s Rock Shop, the Driftless Angler fishing store and Pieces of the Past antiques. Then, wander through the Viroqua Public Market filled with jewelry, gifts and other goods in the historic Main Street Station building.

If you’re a cyclist, either a mountain biker or a roadie, head straight for Bluedog Cycles in its Main Street storefront–the third location in 12 years for this ever-growing business. Ask owner Pete Taylor for anything you need–a rental bike, maps and recommended routes–and he will hold court for a while about your options but never steer you wrong through the Driftless Area.7 Wisconsin Area Road Trips

For road cruising, Taylor will send you down winding and hilly rural roads with a Chamber of Commerce-issued map and urge you to check out the Coon Prairie Trail, a flat 5-mile paved path, which will ease your return to Viroqua from Westby.

But if it’s twisting and technical trail riding through the woods you desire, he recommends Vernon Trails, the stellar 10 miles of singletrack he and volunteers have built at Sidie Hollow County Park, just five miles southwest of town. Trail building is also underway at Jersey Valley County Park north of Westby, with a three-mile trail circling the 56-acre Jersey Valley Lake, the centerpiece of the more developed park.

Although not built or maintained by Taylor’s crew, another 20-plus miles of trail at the 8,600-acre Kickapoo Valley Reserve is open to mountain biking. The multiuse trails there also cater to horseback riders and hikers–and the latter really need to make the trek up to Blackhawk Rock to drink in the view of the valley below.

Back in Viroqua, 40 acres behind VFW Post 3032 includes the 18-hole Bad Axe Disc Golf Club, also built by Vernon Trails and groomed for cross-country skiing and fat biking in the winter.

Taylor’s right: You really can’t go wrong bicycling around the Viroqua area. [AB and JP ]

Sheboygan: More than the Brat Capitol

If you head northeast and drive about two hours, you’ll come across the charming town of Sheboygan, Wisconsin, located on the western shore of Lake Michigan and the mouth of the Sheboygan River.

Stay near the water all weekend at the Blue Harbor Resort, where there are perks for the whole family, such as peaceful spas, an exciting waterpark and breathtaking views of Lake Michigan. Continue your water-themed vacation and rent a sailboat or a stand-up paddleboard to experience each wave and splash of Lake Michigan. Or rent a surfboard and go surfing at North Pier at Deland Park. Who needs California waves?7 Wisconsin Area Road Trips

Enjoy the lush beauty of Sheboygan County parks with a challenging hike or brisk stroll. Check out Kohler-Andrae State Park and you’ll get a full two and a half miles of beach along Lake Michigan with wooded campsites and trails. Just a scenic drive away, you can enjoy a family picnic at the Kettle Moraine Forest for a rustic escape. Explore the surrounding nature even further and uncover a section of the Ice Age Trail, Indian burial grounds and wetland plants and wildlife.

Golf enthusiasts will want to spend the afternoon on the greens along the Lake Michigan shore and grassland dunes at the Whistling Straits golf courses, home to the 2004, 2010 and 2015 PGA Championships. For a form of golfing the whole family can enjoy, check out one of Sheboygan’s disc golf courses, Jaycee Quarry or Vollrath parks.7 Wisconsin Area Road Trips

If it’s a rainy day, spend a few hours at the John Michael Kohler Arts Center, a fun museum full of cool exhibits and galleries. Or grab dinner and see a show at the Stefanie H. Weill Center of the Performing Arts and catch one of the many national touring acts that come through.

Sheboygan is known for its famous hardrolls, brats and cheese curds. After all, you’re still in Wisconsin. However, you will want to try Il Ritrovo Restaurant for authentic Italian food and wood-fired pizza, and the Blind Horse Restaurant & Winery in the neighboring village of Kohler for some wine tasting. Finally, treat your kids (and yourself) to some old-fashioned ice cream on the riverfront at the South Pier Parlor.

Visit Sheboygan for the Independence Day Celebration to marvel at the Venetian Boat Parade, during the WeatherTech international challenge to experience the thrill of race cars at Road America, or to indulge in brats, fried food, music and other entertainment at the Sheboygan County Fair. [DL]

Door County: A Coastal Getaway

It’s been called the Cape Cod of the Midwest, but Door County has landscapes and charm that are purely Wisconsin. The more than three-hour road trip from Madison to this scenic getaway is worth the drive. With more than 300 miles of coastline, the peninsula offers plenty of gorgeous vistas and opportunities to enjoy the waters of Lake Michigan or Green Bay, and the countryside in between.

The eastern edge of the county, known as the quiet side, has beautiful views of Lake Michigan. Stay at one of the waterfront condos at Glidden Lodge Beach Resort near Valmy and be lulled by the waves rolling across the sandy beach right outside your patio door. It’s about two miles south of Whitefish Dunes State Park, which preserves the fragile dune landscape that developed over thousands of years. Lovers of the great outdoors can hike, boat, swim and picnic there, and can camp at other local state parks such as Peninsula, Potawatomi and Newport (which has hike-in campsites). 7 Wisconsin Area Road Trips

Keeping with the nature theme, the Ridges Sanctuary near Bailey’s Harbor is a great place to take a stroll and explore some of the rare flora of the area. The sanctuary protects 1,600 acres of land that includes ridges formed over time from Lake Michigan’s sandy shoreline.

The Green Bay side has plenty of outdoor activities to indulge in, too, but also many interesting shops, eateries and sunset views. On a warm summer day, head to Wilson’s Restaurant & Ice Cream Parlor in Ephraim for a cone and step back in time. The old-fashioned soda fountain and jukebox of oldies have been entertaining guests for years, and it’s an iconic establishment in the Door. Another classic eatery is Al Johnson’s Swedish Restaurant in Sister Bay. Outside it has goats grazing on the sod roof, and inside you’ll find Scandinavian fare from pancakes with lingonberries to Swedish meatballs. If you’re in the mood for a traditional fish boil, try the Viking Grill in Ellison Bay. It claims to be the home of the original Door County fish boil, made with local whitefish and served with baby red potatoes, sweet onions, coleslaw, rye bread and a slice of cherry pie.

Both coasts have a wide variety of options for lodging, from resorts to cottages to bed and breakfasts. Some popular places are the White Gull Inn, a historic bed and breakfast in Fish Creek; the Ashbrooke, located in Egg Harbor and one of the few adults-only hotels in Door County; and Door County Cottages, also in Egg Harbor, for rentals of secluded cabins, cottages and homes.7 Wisconsin Area Road Trips

Throughout the summer there are events and festivals. Catch a live theatrical performance by the Peninsula Players, located between the villages of Egg Harbor and Fish Creek, or visit one of dozens of art galleries. However you choose to indulge yourself, be sure to get your fix of Door County cherries in the form of pies, jellies, juice and a wide variety of other products. The county’s climate and soil are prime for growing cherries and apples, and that’s why the area has 2,500 acres of cherry orchards. Visitors come to Door County every year to pick their own summer harvest.

It’s like a seaside getaway in the Northeast, but it’s all Wisconsin. [KLM]

La Crosse: Riverside Retreat

Whether you’re into fishing in the Mississippi backwater lakes, golfing while overlooking the large, green bluffs and swirling river, hiking for scenic views or just strolling along the river, La Crosse has no shortage of outdoor activities.

Get up close and personal to the bustling Mississippi River and stroll through Riverside Park. Get even closer to the river and board the Queen of the Mississippi, one of the few authentic paddlewheel riverboats still in service today, and take in the lush bluffs, busy wildlife and boundless main channel for a 90-minute tour.

Explore the surrounding nature even further and head to some hiking trails, such as the Hixon Forest trails and the Green Coulee hiking trails. Insider tip: Hike up to Grandad Bluff for a panoramic sunset of oranges, yellows, pinks and purples cascading over the town, river and surrounding bluffs.

Spend some time in the heart of historic downtown La Crosse and seek out the Caledonia Street Antique Mall, with over 40 dealers of authentic, collectible antiques from the surrounding area. Or explore performances, arts and exhibits at the Pump House Regional Arts Center or the Weber Center for the Performing Arts. Don’t forget about performances from two nearby colleges–UW-La Crosse and Viterbo University.

Be sure to dine at some of the local restaurants, such as the Waterfront Restaurant and Tavern for some seafood right out of the Mississippi River, or the Freighthouse Restaurant for a juicy prime beef cut. Don’t forget about dessert! Savor a piece of history at the Pearl Ice Cream Parlor, an original 1930s ice cream parlor offering homemade ice cream, sundaes, malts and shakes, sodas and more.

The area is also home to many local breweries and wineries, such as Pearl Street Brewery, City Brewing Co. and River View Vineyard & Winery. Stop by for a full tour or just a short tasting, depending on the day of the week.

To make the most of your weekend getaway, visit La Crosse during one of its many summer festivals, like the Riverfest taking place from June 30 to the Fourth of July (which has some breathtaking fireworks over the river on the Fourth), Irishfest in August, the La Crosse Area Bicycle Festival over Labor Day or Oktoberfest in the fall. [DL]

Galena: Old-World Charm

The moment downtown Galena, Illinois, comes into view–the multiple church steeples and ubiquitous limestone brick structures cradled by a bucolic valley with the Galena River running serenely through it–you feel like time turned back more than a century.

The city has meticulously cultivated this aesthetic, encouraging its many visitors to take the historic tours that include the former home of U.S. President and Civil War Gen. Ulysses S. Grant, the 1855 DeSoto House Hotel, the 1820s Old Stockade on the Cobblestone Street and several other structures.

The ambiance of Galena is old world, yet it offers considerable upscale shopping on both sides of Main Street. At the Hello Galena artists co-op, more than 65 artists sell their work–from jewelry to pottery, photography to apparel. And at the Artists’ Annex, there are demonstrations of pottery making that take onlookers back to an earlier time.

There are plenty of quirky stores, too, like Ethyl’s (“the place for chicks, wearables and frippery”), For Bare Feet (a socks shop), Wooden Wardrobe and Rustic River Finds, to name just a few.

Galena is also wine country, which is evident at the “Corkless in Galena Wine Festival” at Depot Park on June 24 and again the third Friday of November, when Galena Cellar’s Vineyard & Winery will officially release its Beaujolais Nouveau for the 33rd straight year. Regardless of when you visit, you can sit and sip at Jamie’s Wine Studio or, if spirits are more your thing, Blaum Bros. Distilling Co.

Going even further back in time–when the glaciers scoured much of Wisconsin and Illinois but left a corner “driftless” and replete with hills and valley–the Galena area is consequently a magnet for road bikers and paddlers, too. The 3.4-mile Galena Junction Trail takes riders through the backwaters of the Mississippi River and to excellent bird-watching spots. The Galena River Trail offers another six miles of scenic touring.

Plugged into the outdoor scene is Fever River Outfitters (named after the original name of the Galena River). They’ll equip and direct you on bikeable tours of the area’s wineries and lead you on yoga-kayak combo excursions.

The Galena area is truly stunning, which you’ll be convinced of by visiting Apple River Canyon State Park, Buehler Preserve, Hanover Bluff Nature Preserve or Horseshoe Mound Preserve. All it takes is a weekend there to experience thousands of years of prehistory up through the 1800s. [JP]

Chicago: Tour the Big City

We know the Windy City isn’t in Wisconsin, but it’s only two and a half hours away. Immerse yourself in the art, outdoor activities and the city folk while the weather is still warm.

Start off your day in the Magnificent Mile at Sunny Side Up & Coffee Shop and try the hardy Chicagoan breakfast sandwich. Meander over to the Museum of Contemporary Art and admire the Eternal Youth and the Little Lower Layer exhibits. Walk just one more block and you’ll hit the Lakefront Trail. Whether you head toward Ohio Street Beach and Olive Park or Oak Street Beach and the lakeside cafe, be sure to get a glimpse of the “Playpen,” Chicago’s floating daytime party scene.

Once you’ve had enough of the sand, stop for an afternoon snack at Sprinkles Cupcakes, the legendary cupcake eatery with flavors like banana dark chocolate, triple cinnamon and salty caramel. If the line swings out the door, Sprinkles’ famous cupcake ATM right outside the store delivers you the cupcake of your choice with the swipe of a credit card. How sweet is that?

Get to know the city from a new perspective with the Chicago Architecture Foundation River Cruise. Or head skyward at the John Hancock and venture out onto a ledge to experience the infamous “tilt” firsthand. Experience Navy Pier at night and ride the new, taller Ferris wheel, or sit by Lake Michigan. If it’s a Wednesday or a Saturday, Navy Pier will blow your mind (and your eardrums) with the semiweekly fireworks show.

Keep up to date with the trendiest restaurants like Beatrix for some modern American grub, or Siena Tavern for modern Italian-American dishes. Most importantly, don’t forget to stop by one of Chicago’s deep dish pizza icons like Gino’s East Pizzeria, Pizzeria Uno and Pizzeria Due or Lou Malnati’s Pizzeria.

Branch out from the Magnificent Mile and explore some kitschy retail stores around the intersection of Milwaukee, Damen and North avenues. Stop into Vintage Underground for something shiny, then grab lunch–a ramen bowl at Wasabi, a few tacos at Big Star–or quench that sweet tooth at Mindy’s Hot Chocolate, the summertime favorite run by Mindy Segal, the James Beard Outstanding Pastry Chef award-winnr behind the restaurant/dessert bar.

Summertime in Chicago means a festival almost every weekend. Check out the different neighborhood art fairs, the Taste of Chicago and the Chicago Air and Water Show. If you can extend your trip to last until Monday night or begin it as early as Thursday evening, be sure to check out the Millennium Park Summer Music Series for free music and entertainment. [DL]