United States

The Most Charming Towns and Small Cities in Wisconsin

by Paul Joseph  |  Published July 6, 2021

There’s a lot more to Wisconsin than the  natural scenery characterized by the Great Lakes. Scattered around the midwestern state are a number of towns and small cities dripping with character and charm.

Boats moored in Ashland Marina (Photo: (Photo: visitashland.com))

Sharing coastlines with both Lake Michigan and Lake Superior, the Badger State offers a mix of raw natural beauty,  fascinating social and cultural history, and, of course, delicious cheese and ice cold beer.  Whether it’s exploring the state’s craggy cliffs, enchanting sea caves, or urban centers, there’s an attraction worth visiting at every turn.

Taking all of the above in mind, TravelMag asked more than 100 seasoned adventurers, travel writers, photographers, and industry professionals to name their top three most charming towns and small cities with populations of less than 100,000 people in Wisconsin (excluding Milwaukee, Madison and Green Bay). Below, in alphabetical order, we share the results.


Perched at the base of Chequamegon Bay in northern Wisconsin, the city of Ashland has come a long way since its days as a lumbering, mining, and quarrying heartland. But it’s also a place that has never lost touch with its past, and the series of huge murals dotted around the city’s vibrant business district depicting local historic figures are testament to these enduring links. Also recalling this bygone era are several charming brownstone structures that still grace Ashland’s streets, adding to the city distinctive charm and appeal.

One of 20 murals found on the outside of buildings in Ashland’s historic district (Photo: visitashland.com)


Best known as the hometown of the famous Ringling Brothers, whose traveling circus company captivated Americans throughout the 20th century, the historic town of Baraboo draws many visitors keen to relive those halcyon days of raucous public entertainment. They are able to do so at the Circus World Museum, which offers a magical tour through the history of the Brothers and their nation-trotting act. But there’s far more to Baraboo than juggling clowns—indeed, the town also boasts several enticing restaurants, parks, farms, a spring-fed lake, and a winery.

A bird’s-eye view of downtown Baraboo (Photo: Mike Johnsen)


Situated at the edge of Lake Superior, at the northern tip of Wisconsin, the small harbor town of Bayfield is a popular jump-off point for visits to the magical wilderness of the nearby Apostle Islands. Close to the town are caves that can be explored by kayak, and forests ideal for hiking excursions, while an evening stroll down Bayfield’s Rittenhouse Avenue is one of the highlights of any visit. Lighthouses, Chautauqua tent shows, orchards, a maritime museum, and a vibrant arts scene add to the town’s considerable appeal.


Positioned on beautiful Cedar Creek, 20 miles north of Milwaukee, Cedarburg’s historic architecture is set against a backdrop of eye-catching natural beauty. A harmonious mix of old and new, it is consistently ranked among the region’s most popular small town getaways. The perfectly preserved downtown district is awash with quirky shops, enticing inns, cozy cafes and chic art galleries, which combine with the meticulously maintained buildings to create a destination that positively oozes charm.

Eau Claire

Located at the confluence of the Eau Claire and Chippewa Rivers, this bustling university town has gained a reputation for its indie music and arts scenes, driven by its youthful demographic whose fingers never veer far from the cultural pulse. Lovers of the great outdoors are drawn here too, not least by the water-based opportunities afforded by the two rivers that converge in the heart of downtown. Museums, breweries, public sculptures, parks and a diverse food scene contribute further to the town’s magnetic attraction.

One of the myriad sculptures found in Eau Claire (Photo: visiteauclaire.com)

Fish Creek (Gibraltar)

Many credit National Geographic magazine for the rise of Fish Creek, after the renowned publication ran a story containing a particularly scenic photo of the town back in 1969. The snap helped lead to a tourism boom and today it is a burgeoning resort town that attracts visitors who visit to enjoy the exceptional shopping, endless recreational opportunities, and vast expanse of nearby Peninsula State Park, home to idyllic beaches and bays.

The aptly named Sunset Park in Fish Creek (Photo: James Jordan via Flickr / CC BY-ND 2.0)

Lake Geneva

Whether it’s the sunlight shimmering on the lake, soaring through the air on a zipline adventure, or a fun-filled day on the trails, those with an appreciation of Mother Nature are instantly captivated by Lake Geneva. For more relaxed pursuits, an afternoon of posh pampering at one of the town’s acclaimed spas, followed by a stroll on the shore path admiring the Gilded Age lakefront estates, is just the ticket. Then, perhaps, an evening exploring the unique gift shops and award-winning restaurants of downtown. Whatever your choice, Lake Geneva’s kaleidoscope of events, colors, tastes and wonders make it a worthy inclusion on this list.

A view from the water in Lake Geneva (Photo: atramos via Flickr / CC BY 2.0)

Mineral Point

There are few places that let you walk in the footsteps of the past quite like Mineral Point, nestled in the rolling hills of southwest Wisconsin. Once home to a large community of migrant miners from Cornwall, England, a stroll through the streets takes you past their former homes and workplaces, which are crafted from stone and carefully restored. Indeed, these small dwellings have even been turned into an official museum. What’s more, a thriving community of local business owners, including painters, potters, farmers, and foodies still live here, preserving the legacy of their tough-working predecessors. Local prairies, outdoor trails and tranquil parks add a pastoral touch to a town that still hums with commercial activity.

A row of historic buildings along High Street in Mineral Point (Photo: GPA Photo Archive via Flickr / CC BY-SA 2.0)

Mount Horeb

There’s no escaping the most distinctive characteristic of this little town west of Madison. Take a wander along the primary boulevard of Main Street and soon you’ll encounter one of the life-sized, carved, wooden trolls that adorn the avenue. The background to these quirky figures can be found in the town’s rich Scandinavian heritage, replete with trolls in its folklore, and is also evidenced in the medieval Norwegian stave church that has been the town’s pride and joy since 1937. More contemporary attractions come in the shape of shops and galleries housed within century-old buildings, while on the outskirts of the town you’ll find wineries and artisan farms.

Sturgeon Bay

Tucked between Green Bay and Lake Michigan in Door County, this idyllic, nature-loving town combines its industrial endeavors with plenty of charm. A hip and happening arts mecca and historic shopping districts teeming with eateries, pubs, and coffee shops create a buzzing street scene that’s a match for any of Wisconsin’s major urban centers. Meanwhile, the Sturgeon Bay canal, along with the natural wonders of the Potawatomi State Park and nearby preserves, provide plenty of respite from the hubbub of the town.

Shops along Third Avenue in Downtown Sturgeon Bay (Photo: Richie Diesterheft via Flickr / CC BY-SA 2.0)