For the 50+ Traveler

Southern Wisconsin has not only big, bustling cities like Milwaukee and Madison, but also many charming small towns with interesting things to do. Some have strong connections to their founders’ culture, while others are filled with natural features and historical attractions.

Whether you’re interested in a quick visit or a fun place to linger, these charming small towns in Southern Wisconsin have lots to enjoy. From lively food and beverage scenes to artisan shops and glimpses of the culture of faraway lands, these towns provide the chance to discover and explore.

Tuna tacos from Truk't in Beloit, Wisconsin.

1. Beloit

From the first sip of morning joe at Blue Collar Coffee Co., Beloit charms visitors with its casual approach. The downtown core is stuffed with things to see, do, and eat. The vibe is fun and eclectic, never stuffy, even when upscale. Globally inspired tacos at Truk’t are delicious, as are the over 100 tequilas and whiskeys available from the bar. Swanky dinner at Merrill and Houston’s Steak Joint comes with a river view. The beer scene swings with the Beloit Beer Trail, where you can meander as you'd like, trying many local craft brews along the way. Bushel and Peck’s is a unique one-stop-shop that includes a market and cafe as well as apparel, books, soaps, specialty food products, and more. The Beloit International Film Festival and notable museums like the Logan Museum of Anthropology and the Wright Museum of Art ensure there’s always something interesting in this lively, compact place.

2. Janesville

The parks are some of the most outstanding features of Janesville. In fact, with over 2,500 acres of land and nature trails, Janesville makes the most of its green space. The beautiful Rotary Botanical Gardens and Riverside Park are among the most popular spots. History and architecture buffs will want to explore Janesville’s many historic districts filled with gorgeous buildings and unique stories. For some adult beverages, Fermenting Cellars Winery and Gray’s Brewing Company are great options. Shops like The Glass Garden and several consignment and thrift shops filled with hidden treasures are a shopper’s delight.

Cheese curds and beer in Stoughton, Wisconsin.

3. Stoughton

We first discovered the humorous side of Norwegian culture when we stopped into the Nauti Norske in Stoughton for lunch one day. It was quite relaxing to sit outside and watch the Yahara River gently flow by. The huge list of cocktails and adult beverages relaxed us even further. We managed to get up eventually and explore this utterly charming town that honors its Norwegian roots. Livsreise, the Norwegian Heritage Center, tells the story of Norwegian immigration to the Midwest between 1825 and 1910. Stoughton has lots of cute little shops with Norwegian goods such as the Nordic Nook a few blocks down the street from Livsreise. Fosdal Home Bakery makes wonderful rye bread, donuts, and Norwegian specialties perfect for taking home.

4. New Glarus

The village of New Glarus is bursting with Swiss culture. The adorable town features some buildings with traditional Alpine design, including flower boxes, lots of shops, and restaurants to enjoy. For Swiss cuisine, check out the cozy Glarner Stube. It feels like dining at a chalet in the Alps. Beer lovers will enjoy New Glarus Brewing Company, creator of the Wisconsin favorite Spotted Cow and other great brews. They have a gift shop, a beer garden, and a museum. From time to time, musicians hold brief concerts on their long Alpine horns. The Swiss Historical Village and Museum and the Chalet of the Golden Fleece Museum are fun to explore. Of course, no visit would be complete without indulging in the most famous Swiss edibles -- cheese and chocolate. Maple Leaf Cheese and Chocolate Haus makes it easy by offering both delicacies in one delicious spot.

The National Mustard Museum in Middleton, Wisconsin.

5. Middleton

For a diverse small town with lots to do, Middleton is a great choice. Plenty of parks offer recreation options. The Pheasant Branch Conservancy has plenty of trails for great bird-watching and exploring. Something you won’t find anywhere else is the National Mustard Museum, with some 6,000 different mustards from all around the world. It’s a fun place to wander through, learn about this yummy condiment, and even purchase something unique to take home. The award-winning Capital Brewery resides here, and downtown Middleton is full of great food, too. One of our favorite spots is the Hubbard Avenue Diner, filled with diner classics and unforgettable pie. Longtable Beer Cafe is a great spot for handcrafted food and beer and has a bottle shop where you can buy craft brews to take home. Hurts Donut makes jumbo donuts in crazy flavors to satisfy even the sweetest tooth.

6. Mount Horeb

The residents of Mount Horeb have a special affinity for trolls, turning their charming small town into the Troll Capital of the World. If you fancy a troll stroll, you can look for these carved wood mythical creatures at some two dozen locations. Grab a bite at the Grumpy Troll Brew Pub or one of many other great dining spots. Tyrol Basin has fun winter activities like skiing, snowboarding, tubing, and scenic chair lift rides. Artisan shops display unique items like woodcrafts, handmade soaps, antiques, jewelry, and gifts. For some outdoor fun, Linstroth Valley View Farm specializes in fall produce. You have your pick of pumpkins, squash, potatoes, onions, carrots, and beautiful fall decorations like corn stalks, colorful mums, Indian corn, and decorative gourds.

Green County Cheese Days in Monroe, Wisconsin.

7. Monroe

Monroe is known as the Swiss Cheese Capital of the U.S. The National Historic Cheesemaking Center makes a fun place to visit, offering lots of history and information about the cheesemaking process. Then for some cheesy treats, head to Alp and Dell Cheese Store to check out their large selection of cheeses and other goods. If an immediate cheese and beer fix is needed, Baumgartner’s pub has great beer choices, a simple but tasty menu with lots of cheese items, and intriguing wall art featuring scenes of cheesemaking and a battle between wine bottles and beer steins. Cheese fans from all over gather in Monroe for the annual Green County Cheese Days celebration where cheesemakers compete and cheese lovers eat all kinds of cheese. Celebrated since 1914, Cheese Days has its own cheesy theme song and a mascot, Wedgie.

8. Blue Mounds

Blue Mounds is the perfect spot for a dose of natural beauty. Blue Mound State Park has gorgeous views from the highest point in Southern Wisconsin. Cave of the Mounds is an interesting natural limestone cave filled with unique mineral formations. For a chance to get up close to some pretty adorable animals, stop by Havens Petting Farm. They’ve got many friendly critters like alpaca, ponies, mini potbellied pigs, bunnies, mini donkeys, fainting goats, and more. This indoor-outdoor farm offers plenty of smiles, sometimes goat yoga, pony rides, and other fun activities. Leave your grown-up self-restraint at home and cuddle up with a bunch of kids (goats, that is).

The town of Dodgeville, Wisconsin.

9. Dodgeville

The charming town of Dodgeville rests serenely among rolling hills, lovely lakes, and rugged bluffs. Doby Stables provides great horseback riding on picturesque trails through the scenic Dodgeville landscape. You can explore Governor Dodge State Park by foot, horseback, bicycle, boat, kayak, or stand-up paddleboard in summer and snowmobile or skis in the winter. Bob’s Bitchin’ BBQ is a local favorite eatery for slow-smoked meats, while Duke’s Brew Pub and Ale House is a lively spot with a great rotation of local microbrews. Visit Folklore Village to learn about folk arts and the cultural traditions so important to this town.

10. Mineral Point

Established by miners from Cornwall, England, the charming town of Mineral Point transports you with its historic architecture and stone houses. Shoppers delight in specialty retail boutiques, art studios, and galleries. The Mineral Point Railroad Museum offers a peek into the historic depot, built in 1856 from local materials, that became the oldest rail depot in Wisconsin. Other attractions include Pendarvis Historic Site with homes built in the 1840s and the Gundry House Museum, an expansive mansion with beautiful grounds. Cornwall’s spirit lives on in Mineral Point with gift shops like The Cornish Corner and The Mineral Point Collection. Taste delicious Cornish pasties at fun spots like Red Rooster Cafe and Walker House. Check out the annual Cornish Festival for a full array of food and entertainment.

Taliesin, Frank Lloyd Wright's home in Spring Green.

11. Spring Green

Most people know Spring Green as the home of Taliesin, Frank Lloyd Wright’s home, studio, and school of architecture. And certainly, when visiting Spring Green, this 800-acre estate is a must-see. Another attraction is the unusual House on the Rock. Originally the owner’s dream retreat, the house has expanded into an ever-evolving collection of exotic and unusual items that fill themed rooms and outdoor gardens. Tower Hill State Park offers gorgeous river views, hiking trails, and picnic areas. The Spring Green General Store is a special place where you can find curated gifts handcrafted by local artists and carefully prepared meals from the cafe. They host the incredibly popular BobFest (honoring Bob Dylan) and BeatleFest outdoor events that bring music fans together to celebrate the songs.

Wisconsin’s towns come in many shapes and sizes. Some of our very favorites are tiny but mighty. We hope that you’ll visit some of these charming small towns in Southern Wisconsin if you have the chance.