7 Wisconsin Destinations for Small-Town Charm

When’s the last time you really felt like time slowed down and you got to relax, recharge and spend quality time together?  If that sounds like a dream come true, then make it a reality in these 7 charming small towns in Wisconsin. With rich history, culture and idyllic downtowns, these hidden gems are places you’ll keep coming back to for more memories.

New Glarus: Alpine Flavor

Women shopping at Brenda's Blumenladen in New Glarus

What makes a small town the perfect one to explore? The old-fashioned charm, spirited atmosphere and story behind it, of course! New Glarus is called “America’s Little Switzerland” for good reason as it was originally settled by the Swiss in the mid-1800s. When you explore this town, you’ll even hear Swiss music piped downtown. To feel enriched with New Glarus’s culture, check out the Swiss Historical Village Museum. And to take in the outdoor charm together, bike the 23-mile Sugar River State Trail.

Food & Drink


Here, the months go August, September, Oktoberfest, November and December (if you know you know). New Glarus is known for their annual Oktoberfest (usually held at the end of September) and this bright festival is filled with music, beer and great times. Another stop to enjoy craft beer is the New Glarus Brewing Company. Or listen to live music and sip on beer at Puempel’s Olde Tavern. And if you have a sweet tooth, head to New Glarus Bakery with friends, as they have been serving Swiss delicacies for decades.

Best Fests: New Glarus clearly is life of the party. There’s Polkafest, Swiss Volksfest (Switzerland’s Independence Day), Wilhelm Tell Festival, and the legendary Oktoberfest.

Chippewa Falls: Lakes and Leinie’s

Chippewa Falls is known for its natural beauty being home to Lake Wissota and hundreds of miles of bike trails.

Food & Drink


Satisfy your hunger with retro eateries at every corner in this small town — and each one has a unique twist. Known for a lakeside view and live music, The View is perfect for catching up with friends. For delicious cheese curds and top-notch Bloody Marys, try the SandBar and Grill. For a classic Wisconsin fish fry, The Edge Pub & Eatery is the a must-stop. Overlooking the Chippewa River is Loopy’s Grill & Saloon where you and your crew can play volleyball year-round and partake in refreshing river tube floats in the summer. The city’s oldest business is Leinenkugel’s, which started brewing their delicious brews in 1867. It’s the seventh-oldest working brewery in the nation! Take a tour of the impressive facilities—they run daily and  start in the famous Leinie Lodge.

Take in the Views

Known for a gorgeous view and a spot to sit back and relax with friends and family, the Hideaway Resort is the place to stay with its six year-round cabins along Lake Wissota. In the warm weather months, bike the Old Abe State Trail or paddle one of the area’s 450 lakes. Come winter, get out the ice fishing equipment, cross country skis and snowmobiles to make snowy memories with your crew. Or check out the Irvine Park and Zoo for a family day trip.

So Sweet: Have a sweet tooth? You’re in luck with Olson’s Ice Cream and the Chippewa Candy Shop. Enjoy your trip with an ice cream cone in one hand and a chocolate truffle in the other.

Baraboo: Breathtaking

Baraboo is a place to explore known for adventure every step of the way.

Take in the Views


Right outside of Baraboo, Devil’s Lake State Park is Wisconsin’s most-visited state park with towering quartzite cliffs and a crystal-clear lake surrounded by 500-foot-high bluffs. Another go-to stop is the Aldo Leopold Foundation. This is a great place to appreciate and wander in nature with friends or little ones. You can also check out the International Crane Foundation, the only place in the world where you can see all 15 species of cranes; and a picture-perfect courthouse square, a focal point of this community, with bustling boutiques and cafes circling it. Be sure to get to Bekah Kate’s specialty home goods store, Cornerstone Gallery, Neat-O’s Bake Shoppe, Little Village Café, and Con Amici Wine Bar for a full weekend (or week!) of one-of-a-kind shopping. 

Can’t Miss: Baraboo was the winter quarters for the stupendous Ringling Bros. Circus, and to celebrate the history, visit Circus World. See spectacular circus shows the kids will love and marvel at the colossal collection of restored antique circus wagons. Downtown, the Al Ringling Theater glistens like the gilded jewel it was when it first opened in 1915, thanks to a multi-million-dollar restoration. Stay at the Ringling House B&B, the original home of one of the Ringling brothers.

Princeton: Treasures To Be Found

For the itinerant treasure hunter, Princeton is your kind of town. It's home to the state’s largest outdoor flea market, held every Saturday mid-April through mid-October.


When you’re done there, head to more antique spots dotting the community like MNM Antique Mall and Woolbrights River City Antique Mall. For modern goods, there’s Twister for kitchen gadgets, and Daiseye for earth-friendly apparel.

Refuel with a Reuben sandwich at Buckhorn Bar & Grille.

Elkhart Lake: Stylish, Relaxed

This lakeside village has lots of charm. There are white clapboard resorts with porches and cupolas, sandy beaches, tiki bars, and a pretty brick promenade, all positioned to take best advantage of the Mediterranean-like blue waters.

You'll notice the friendliness — it's normal for guests to pop in to say hello to the owners upon arrival at resorts like the Osthoff Resort, Siebken’s and the Shore Club.

Adding to the charm is that nearly everything is walkable. Stroll in one direction and you’ll find yourself at Two Fish Gallery and Sculpture Garden. In the other direction, discover Gina’s for high-end outdoor apparel and home décor items. And smack dab in the middle is Vintage, a wine store with tasting room for delicious afternoons spent with friends.

Bikes are a common sight, too, with serious pedaling in the Kettle Moraine a major draw. Racing at Road America is the modern iteration of the road racing once staged through the streets of the village.

Most Unexpected: The culinary scene in Elkhart Lake is a hidden gem ready to be explored by you and your group. Start at Off the Rail Cafe for coffee drinks and breakfast goodies, Lake Street Café for lunch, Gesserts for ice cream, Paddock Club or the Concourse Restaurant for fine dining, and Brown Baer for drinks and live music.

Cambridge: Pottery Put It on the Map

Pottery put Cambridge on the map of charming destinations starting in the late 1980s when the community carried the title of “salt glaze pottery capital of the world,” setting the stage for quaint shops and restaurants to open. Today, Rowe Pottery Works continues to help define the village as an artists’ enclave. There’s also Cambridge Wood-Fired Pottery where you can explore more artistic styles.

For urbanites looking for a break from the busyness of their workaday lifestyles, explore the gorgeous 422-acre CamRock Park system by foot or bike.

Famous Names: Cambridge was home to two inventors with names you may recognize. Ole Evinrude, inventor of the outboard motor, and Arthur Davidson, one of the founding members of Harley-Davidson motorcycles, came to live in Cambridge in the late 1880s. Fast-forward and you can add race car driver Matt Kenseth to the list of prominent locals.

Stockholm: A Slice of Perfection

Couple enjoying wine in apple orchard at Maiden Rock Apples, Winery & Cidery in Stockholm

Stockholm is a sweet destination along the Great River Road, it’s populated with galleries, boutiques, and a unique performing arts center. Be sure to stop in the world-famous pie shop, Stockholm Pie and General Store, where Triple Berry is the best seller, but the flavor options are almost endless.  

The town has preserved its Swedish roots through one-of-a-kind attractions. Scandihoo is a destination with fine Scandinavian treasures. Maiden Rock Winery and Cidery offers European-style hard ciders, and Vino in the Valley charms guests with outdoor dining and fantastic wines. A to Z Produce and Bakery is known for their pizza nights where the ingredients are locally grown. The Widespot Performing Arts Center season starts in autumn and hosts a wide variety of dazzling entertainment. 

Geography Lesson: Stockholm overlooks Lake Pepin, the widest spot on the Mississippi. Hike out to Maiden Rock Bluff Natural Area to get a view of the glimmering water or walk the 700-foot stone pier that juts out into the river for unforgettable views in this picture-perfect location. 


Craving more small town charm? Check out these small towns that feel like the set of a holiday movie.

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