If you’ve ever wondered where to find the best downtowns in Wisconsin, you need to visit its charming small towns. To find the real beauty and character of Wisconsin, all you need to do is step onto Main Street. The Dairy State has 1,852 cities, towns, and villages and there are a million great reasons to explore these places – you’ll find charming shops, one-of-a-kind restaurants, historic spots, and more. Some small towns are especially worth seeking out. Here are seven towns that have some of the best Main Streets in Wisconsin.

1. Stoughton
Stoughton, WI 53589, USA
Facebook / City of Stoughton, WI
Step into old Norway in this city that’s a short drive south of Madison. Pick up some old-school baked treats or explore historic buildings holding interesting shops and boutiques. Start planning your trip to one of the best small towns in Wisconsin.
2. New Glarus
New Glarus, WI 53574, USA
Facebook / New Glarus Chamber of Commerce
This town is like a Swiss colony – the postage-stamp-sized downtown is packed with old-world charm. Stop into a classic tavern and order a pint of the town’s beloved beer – Spotted Cow. Be sure to add this charming town in Wisconsin to your bucket list.
3. Sturgeon Bay
Sturgeon Bay, WI 54235, USA
Facebook / Destination Sturgeon Bay
This old shipbuilding town in Door County has become a tourist Mecca, and the downtown has been transformed into a charming and welcoming vacation spot. The city’s canal still sees the passage of some large ships and it’s a beautiful backdrop to the town. Start planning your visit to this small town with some of the best downtown shopping Wisconsin.

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4. Mineral Point
Mineral Point, WI 53565, USA
Facebook / Destination Sturgeon Bay
The lead miners are long gone but the town they built remains and it’s one of the prettiest spots in the state. It was founded in 1827 and is home to gorgeous 19th-century buildings which hold galleries, shops, and restaurants. Learn more about one of the best downtowns in Wisconsin, and then plan your visit there.
5. Bayfield
Bayfield, WI, USA
Facebook / Bayfield and the Apostle Islands
In far northern Wisconsin, Bayfield is the gateway to the famous Apostle Islands. When you see the charming downtown, you might decide to stay right where you are. It’s packed with charming boutiques and welcoming bars and restaurants. Go ahead and plan a day trip to one of the best small towns in Wisconsin.
6. La Crosse
La Crosse, WI, USA
Facebook / Downtown La Crosse
You’ll still see riverboats drifting past this historic downtown on the Mississippi River. La Crosse is a vibrant university town and there’s always something happening downtown – it hosts lively festivals, concerts and more. Learn more about this charming town in Wisconsin, and then pencil in a visit.
7. Ripon
Ripon, WI 54971, USA
Facebook / Ripon Chamber of Commerce
The final stop on this tour of Wisconsin is the charming little college town of Ripon. Known as the birthplace of the Republican Party, Ripon’s downtown is filled with revitalized buildings holding lively pubs, coffee shops and restaurants.

These are some of the best downtowns in Wisconsin. If you love exploring Wisconsin, here are 10 of the oldest towns you’ll find.

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best downtowns in Wisconsin

Jessica Bohl | September 19, 2022

What are some beautiful small towns in Wisconsin?

Small towns abound in Wisconsin, so there is always a great place to escape to from the hustle and bustle of life. For those who love the beauty and charm of small towns, you will want to check out the picturesque town of Sister Bay. It is a great place for a quiet escape, but also has plenty to do, including scenic kayaking on Green Bay. Stockholm is another picture perfect town in Wisconsin. It has breathtaking views of Lake Pepin and its quaint charm is idyllic. Start planning a weekend trip to one of these beautiful small towns.

What are some historic towns in Wisconsin?

Wisconsin has a long history that even goes back to before the Revolutionary War. So there are plenty of historic towns and attractions to check out. Take for instance, Shullsburg, which dates back to 1827. Settled most by Irish prospectors, the town has many historic town buildings, and Water Street has even been designated a National Historic Landmark. Prairie du Chien was established in the late seventeenth century by French voyageurs. The town’s name comes from the Fox Indian chief who resided in the area at the time. The town served as an important trading post and today has 5 National Historic Landmark designations and 9 sites on the National Register of Historic Places. Spend the day at one of these great, historic towns.

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