Visit These 12 Incredible Charming Small Towns in Wisconsin, One for Each Month of the Year

There’s a lot to discover in the small towns of Wisconsin, but there’s a little catch – there are a lot of them! There are more than 1,200 towns in the Dairy State, plus over 400 villages and nearly 200 cities. If you would like to choose some to visit, here are some of the very best Wisconsin small towns that have great shops, restaurants, and history. Visit them this year—here’s where to go.

1. Port Washington

The lakeside community of Port Washington is located just north of Milwaukee. With a gorgeous waterfront and a historic downtown filled with charming shops and restaurants, this is one of the most charming towns in Wisconsin. Would you like to spend the night when visiting Port Washington? Book a stay at The Harborview, a hotel within walking distance to Lake Michigan.

2. Ephraim

In the 1800s, Moravian immigrants settled this little village and it hasn’t lost its lakeside charm. Take in an awesome sunset on the gorgeous and walkable waterfront, take a stroll along a quiet road, or even take a boat out on the water. Ephraim is one of the best towns to visit in Wisconsin, perfect for a weekend getaway.

3. New Glarus

When you arrive in this Green County hamlet, you might feel like you’ve stepped into the old country. In a way, you have—New Glarus is incredibly proud of its Swiss heritage and it's eager to blow its horn! If you'd like to feel as though you're in Switzerland, book a stay at the 'Ott to Yodel' chalet in New Glarus.

4. Platteville

This Wisconsin town grew up during the state’s early mining days. While the lead boom is long over, you can still explore mining history here and even climb a giant M just outside of town. Platteville is one of the most historic towns in Wisconsin, and it's worth taking a weekend getaway here.

5. Mount Horeb

If you visit Mount Horeb, you’ll have some unusual company downtown. This town is filled with large troll statues, as well as a nice mix of stores and restaurants. It also has some unique accommodations including a cozy and stylish earthen home.

6. Bayfield

For a trip you won’t forget, head to far Northern Wisconsin. The little town of Bayfield has it all including sea caves, offshore islands, apple orchards, art, and more. And if you're searching for a hotel, take a look at the St. James Social, a boutique hotel with a rooftop terrace.

7. Pewaukee

Longtime locals remember a time when the Pewaukee waterfront wasn’t lined by adorable shops. Live in the now — get an ice cream and soak up the sun on the town's walkable stretch of stores and restaurants before heading back to your hotel.

8. Trempealeau

Flanked by towering bluffs along the Mississippi River, this little town is the gateway to a beautiful state park. Enjoy a hike with incredible views and then tuck in for a cozy meal at the Little Bluff Inn as river barges drift by.

9. Stockholm

Feeling hungry for pie? Head to this charming waterfront town to get your fill of the state’s best pie, as well as a great view of Lake Pepin. And as one of the most historic towns in Wisconsin, there are some fascinating vacation rentals you can spend the night like the Updated Historic Schoolhouse.

10. Sparta

If you’re looking for great local flavor, look no further than Sparta. The town holds lively events throughout the year, including a picture-perfect holiday market.

11. Mineral Point

There was a time when this little town was the center of the state’s mining industry. Those days have passed and today Mineral Point is known for its big collection of art galleries. It's also one of the most charming towns in Wisconsin for a weekend getaway.

12. Monroe

There’s just one decision you’ll need to make when you visit this town in southern Wisconsin. Beer or cheese? The town has some iconic offerings and fortunately, they pair very well together. Do you know what also pairs well? A stay at the 2,000-square-foot MJ's Penthouse that's within walking distance to all the best that Monroe has to offer.

Once you’ve explored these small towns in Wisconsin, here are some more unforgettable day trip ideas.