Fun and adventure are just a tank of gas away! Wisconsin is filled with charming small towns that offer it all – delicious local restaurants, historic sights, scenic natural areas, and more. These little towns are ideal spots for a weekend getaway. Here are some of your wonderful cool small towns in Wisconsin you ought to add to your Wisconsin bucket list ASAP:

1. Stoughton
Stoughton, WI 53589, USA
Facebook/ Visit Stoughton, WI
Step into the old country with a visit to Stoughton. Located just south of Madison, this charming town wears its Norwegian roots on its sleeve. You’ll see this heritage in the community's charming shops, galleries, restaurants, and museums. Each May, everyone is Norwegian for a day here during the community’s annual Norwegian Syttende Mai celebration. Join the fun!
2. Ripon
Ripon, WI 54971, USA
Facebook / Ripon, WI
Budget Travel magazine named Ripon one of the "Coolest Small Towns in America" and when you arrive you’ll understand why. The town has tons of history – it's home to a 150+-year-old college and the Republican Party was founded here. The downtown is filled with lively pubs, restaurants, and coffee shops. It’s the perfect small-town Wisconsin getaway.
3. Baraboo
Baraboo, WI 53913, USA
Facebook / Baraboo Area Chamber of Commere
This little town is the gateway to some great things. Baraboo is located next to Wisconsin’s most popular state park, Devil’s Lake State Park. It’s also home to the amazing Circus World Museum and the International Crane Foundation. It’s a wonderful place for a family escape.

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4. Sparta
Sparta, WI 54656, USA
Facebook / Elroy Sparta Trail
Cyclists: Sparta has your ticket to ride. This little town is known as the "Bicycling Capital of America." Load up your bike and explore several nationally known bike trails, including the Elroy-Sparta State Trail which was the first rails-to-trails bicycle route in the country.
5. Waupaca
Waupaca, WI 54981, USA
Facebook / Visit Waupaca Chain O'Lakes
Water lovers need to look no further than Waupaca for a summer getaway. This town is located in the Chain O' Lakes – it’s an awesome spot for boating, swimming, kayaking, touring, and fishing. While Wauapca is not as well known as some of the destinations in the Northwoods, it’s an easier drive from places like Milwaukee and Chicago so you can get on the water sooner.
6. Merrill
Merrill, WI 54452, USA
Tripadvisor / Management
A lot of vacationers pass this town on their way north but they would be wise to stop. The community along the Wisconsin River has it all – charming historic homes, picturesque stone arch bridges, and scenic outdoor recreation areas. Merrill is an ideal place for a weekend getaway.
7. Richland Center
Richland Center, WI 53581, USA
Facebook / Greater Richland Center Area Chamber
This picturesque town is surrounded by dairy farms and tree-covered hillsides. Richland Center is tucked in the Driftless Area of Wisconsin and it's the perfect base to explore the scenic southwest area of the state. You’ll find everything from historic architecture to local wineries and hiking spots.

Are you ready to explore one of these cool small towns in Wisconsin? What other small towns would you add to this list? Let us know in the comments!

If you’re looking for some more fantastic road trip ideas, take a look at these unforgettable destinations in Wisconsin.

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More to Explore

Cool Small Towns in Wisconsin

Tori Jane | September 20, 2022

What are the best weekend getaways in Wisconsin?  

Wisconsin isn’t exactly known for its wild nightlife or premier vacation spots, and we feel like that’s too bad. Turns out, there are all kinds of amazing places in Wisconsin that are perfect for a quick escape. Some of our all-time favorite day trips in Wisconsin include heading to places like Big Manitou Falls, which is an awesome place for nature lovers, and the state parks of Wisconsin are another set of excellent options. You can go camping, hiking, boating, and more in all the same places – you just need to pick one, which is the hard part. Head out to Door County and enjoy one of the best places to visit in Wisconsin. Visit Madison or Lake Geneva. Seriously – start planning ASAP!  

Which Wisconsin small towns should I add to my bucket list?  

Life in Wisconsin is a lot more scenic than you might expect; it’s a beautiful place with plenty to see and do, especially if you’re a fan of nature. Some of the best small towns in Wisconsin to visit include gems with plenty of natural beauty to go around, like Sturgeon Bay, which offers postcard-esque views of the bay and incredible sunsets to boot. We also love Janesville, which is excellent for fans of local history, Stockholm, a tiny town with less than 100 residents that’s perfect for anyone who needs some peace and quiet, and Eau Claire, a college town with more than enough to do and see.  

What are the best small towns in Wisconsin for families?  

So how many of these small towns in Wisconsin are good for families? All of them. Seriously. Of course, we can go on with our list – and it isn’t short! Milwaukee is an excellent city for families, but sometimes you need something smaller and more intimate, and in that case, check out towns like Kohler, Nashotah, Bayside, Verona, Cross Plains, North Hudson, and so many more. It might seem overwhelming at first, but we promise the small towns of Wisconsin are worth visiting – or living in!  

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