7 Underrated Small Towns to Explore in Wisconsin

A Lake Michigan shoreline and troll-lined streets capture the variety found in the seven most underrated small towns across Wisconsin. Algoma highlights that appeal with the Algoma Light and von Stiehl Winery (Wisconsin’s oldest licensed winery!), giving this lakeside community a strong sense of history. Farther inland, Mount Horeb adds its own distinctive draw through the Trollway, where 36 carved figures line downtown and create one of the state’s most memorable main streets.

Between those highlights, the remaining destinations bring a quiet mill pond, Mississippi River bluffs, Driftless hills, and the restored Villa Louis estate! Together, these 7 stops each create their own smooth mix of scenery, history, and small-town character.

Algoma

Situated on the far eastern side of the state, Algoma is a lesser-known locale on Lake Michigan. It is home to roughly 3,200 people and whimsical attractions like Wienke's Market, Steele Street Trading Co and Gallery, the Algoma Light, and the von Stiehl Winery. The last of those has been operating since 1967 and is considered Wisconsin’s oldest licensed winery. Though part of Kewaunee County, Algoma is the entranceway to Door County, which covers a peninsula characterized by beaches, bluffs, and caves and the many ways to see them, such as by car, boat, plane, trolley, and Segway. Open up to an excursion in an unsung enclave of America.

Amherst

Amherst is a charming little spot in the Tomorrow Valley that truly feels like stepping back in time. Visit Amherst on the 19th century, thanks to its beautiful old storefronts and the rustic charm of Mill Pond. You can immerse yourself in this nostalgic atmosphere, or add a bit of adventure by boating on the Mill or exploring the modern businesses tucked inside the historic buildings. For some comforting bites, stop by Ambrosia Pub & Grill, housed in an unassuming Main Street building, or visit The Local Goat Company just outside downtown for some delicious local fare. One of Amherst's standout favorites is Central Waters Brewing, which has been creating sustainable beers for 26 years. After soaking up the village’s charm, be sure to visit the neighboring town of the same name, especially Lake Emily Park, with its beautiful 143 acres to explore.

Trempealeau

Trempealeau is a town, an adjacent village, and their shared county. According to the Wisconsin Historical Society, that unique, multi-purpose name comes from the French phrase "La montagne qui trempe a l'eau," which in turn comes from an Indigenous translation of "soaking mountain" or "mountain separated by water." Sure enough, this region is overlooked by Trempealeau Mountain, a 425-foot-tall rock island separated by the Mississippi and Trempealeau rivers. To see one of the Mississippi River's only "mountains," head to Trempealeau the village, fuel up at Sullivan's Supper Club or the River Cafe, and then tramp northwest to Trempealeau the town, which contains Perrot State Park. Perrot is where Trempealeau Mountain and its woodlands are preserved as the Trempealeau Mountain State Natural Area. To uncover more overlooked natural gems, hop on over to the Minnesota side of the Mississippi, on whose bluffs exist Great River Bluffs State Park.

Viroqua

Viroqua is a charming place that shares its name with both a city and a town in the far western part of Wisconsin. According to the 2020 Census, the town is home to 1,744 residents, while the city has a population of 4,504. Naturally, the city is a little livelier and full of energy. It offers a variety of lively spots like the Historic Temple Theatre, Ewetopia, the Viroqua Food Co+op, Driftless Books & Music, and the cozy Driftless Café. Like many communities in the beautiful "Driftless Area" of Wisconsin, Minnesota, Iowa, and Illinois, Viroqua is surrounded by breathtaking natural scenery. After browsing the bookstore or enjoying a meal at the café, you can explore Sidie Hollow Park, Wildcat Mountain State Park, the Duck Egg County Forest, and of course, the majestic Mississippi River.

Black Earth

If Tomorrow Valley is Wisconsin's Shire, Black Earth is its Mordor. Don't worry, that comparison is just in name! Black Earth is a lush, green oasis that actually refers to a charming village and town in south-central Wisconsin. The most beautiful green spots nearby include Morton Forest, Salmo Pond County Park, and the Black Earth Rettenmund Prairie State Natural Area. With only around 2,000 residents, this peaceful countryside feels surprisingly vibrant, especially considering the impressive modern establishments that stand out here. The village of Black Earth is home to the Black Earth Children's Museum, a wonderful community-supported space with over 50 handmade exhibits. Not far away, The Shoe Box is known as the "Midwest's largest shoe store,' boasting about 300,000 shoes! And here's a fun sight—King Kong's sculpture watching over Black Earth from atop The Shoe Box.

Prairie du Chien

Prairie du Chien is a charming and often overlooked community in the Driftless Area, known for its rich history and natural beauty. Tucked away between the Mississippi and Wisconsin river bluffs, it quietly offers a wonderful mix of scenic, cultural, and lively experiences. Take a leisurely walk in "Dog's Meadow," grab a treat from Simply Cafe, enjoy a refresh at Fort Mulligan's Grill Pub, or explore the beautifully restored Villa Louis Historic Site on a Mississippi island accessible by bridge. Prairie du Chien truly stands out as a gem in western Wisconsin, offering something special for everyone.

Mount Horeb

Mount Horeb should be the highlight of your middle Wisconsin adventure. This charming village, home to around 8,000 residents, is just 10 miles south of Black Earth. It’s a quick four-hour walk for your group to reach it. When you arrive, you'll be warmly welcomed by a delightful surprise—trolls! That's right, no kidding. Thirty-six beautifully carved and sculpted trolls line the

But Mount Horeb's troll identity is not hollow. Well, it literally is. Just a few miles west of town is a 750-foot-long cavern called Cave of the Mounds that looks like the birthplace of the 36 trolls. Who knew such a magical place existed in rural Wisconsin?

We hope you did not mind us badgering you about underrated Wisconsin towns. Trempealeau, Viroqua, Amherst, Black Earth, Algoma, Prairie du Chien, and Mount Horeb deserve attention for their natural and commercial wonders, especially Trempealeau Mountain in the first community and the Grumpy Troll Brewpub in the last. As such, we implore you to dig for the Badger State's treasures rather than stay surface level during your next vacation.