5 Small Towns in Wisconsin You Must Visit

Sister Bay

Photo courtesy of Sister Bay, Door County Tourism.

By Jessica Lee
November 8, 2022

Wisconsin is full of small towns with beautiful scenery and charm. Here are some that make for a perfect day trip.

Wisconsin doesn’t have the sprawling urban areas found in many other states. Instead, outside the state’s major cities, visitors will find several mid-sized cities and hundreds of small towns. Each small town has its own character and sense of community, some with breathtaking scenery, fascinating historic sites, and fun attractions, always providing the perfect backdrop for a day trip, weekend getaway, or longer. 

Here are some of our favorite small towns in Wisconsin that you must visit. 


Cassville Stonefield historic site
Photo courtesy of Cassville Tourism

With fewer than 1,000 people, Cassville is a small town on Wisconsin’s Great River Road that often gets overlooked for bigger cities along the Mississippi River. It’s one of the oldest towns in Wisconsin and the southernmost town in the state that is directly on the banks of the river. The Cassville Car Ferry provides an easy crossing to Iowa’s Great River Road, but there’s plenty to do in this little town without going to another state.

Visit the historic Deniston House, which was built to house legislators and government officials because Cassville was in the running with Madison to be Wisconsin’s capital. Outdoor enthusiasts and birdwatchers cannot skip a trip to Nelson Dewey State Park, where bald eagles live and soar. Finally, a visit to Cassville is incomplete without a trip to Stonefield Historic Site, a replica of a 1900s rural Wisconsin Village maintained by the Wisconsin Historical Society. 

Lake Holcombe

Image via Public Domain

Wisconsin is full of lakes and rivers where residents and visitors can swim, ski, fish, icefish, kayak, and more. Lake Holcombe is one of Wisconsin’s many hidden outdoor paradises. The city’s namesake is actually Holcombe Flowage, a reservoir along the Chippewa River, but used to be called Little Falls when the dam was built in the 1800s. The dam stands between Birch Creek and Lake Holcombe and was once the world’s largest “right angle” wooden dam. 

The town is quaint with a few shops to check out, but the real draw is the resorts, taverns, and water. Whether you go boating in the summer or snowmobiling in the winter, you can enjoy a meal at great restaurants like Phat Bobs at Big Swede Resort and the Eastbay Lodge. Also, check out some of the local taverns like the Big Minnow Bar, Grill and Bait Shop, and Pine Drive Bar and Grill

Sister Bay

Door County is full of quaint, small towns and Sister Bay is among the best of them. This small town, with around 1,000 people, is chock full of activities throughout the year. You can find all the fun water activities you come to expect from Door County in the summer, including swimming at Sister Bay Beach and boating, fishing, and other watersports in the bay and in Lake Michigan. For an indoor activity, check out the Corner of the Past Historical Museum, which features a renovated farmhouse and restored farm buildings that showcase what life was like in the area in the late 1800s. 

READ MORE: The 4 Best Small Towns for Small Business Shopping in Wisconsin

Trying some Swedish pancakes at Al Johnson’s Swedish Restaurant is also a must. If you visit during the summer and fall, you will likely find goats relaxing and eating grass on the restaurant’s sod roof. Adults and kids alike love Pirates Cove Adventure Golf as a way to relax and have some family fun during your visit. Sister Bay is also home to several festivals and celebrations throughout the year. Depending on when you visit, you might enjoy the Door County Festival of the Arts, the Sister Bay Easter Egg Hunt, or the Sister Bay Fall Fest. 


Cascade Falls
Photo courtesy of Steve Papineau

Located along the St. Croix River, Osceola is a small Wisconsin town you don’t want to miss. The historic downtown has various antique shops and boutiques, making it a favorite day trip for those from the Twin Cities and other parts of Wisconsin. After you check out The Looking Glass, Coming Home, and others, you can grab a bite at one of the bars or restaurants downtown. Try for a strike after you order a burger at Osceola Lanes or head to Watershed Cafe for locally sourced farm-to-table deliciousness, where you can head behind the restaurant to catch a glimpse of the breathtaking Cascade Falls. 

Consider visiting Osceola when the Acreage, 360 acres of woodland and prairie on the bluffs above the St. Croix River, holds an event. The property was once the home, farm, and retreat of Horst Rechelbacher, founder of Aveda. Today, the Acreage carries on Rechelbacher’s legacy as a place to educate and inspire people about sustainable conservation. 

Williams Bay

Lake Geneva is a popular tourist destination for Wisconsinites and nearby Illinois residents. The name refers to the lake and the town on its shores. However, two other towns lie on Lake Geneva’s shores and Williams Bay is one of them. During the summer, visitors will enjoy the treelined, sandy Williams Bay Beach where they can catch the Lake Geneva Shore Path and walk as far as they want around the lake. 

Staying in Williams Bay provides some relaxation and peace that sometimes isn’t available on other parts of the Lake. Yet, it’s only a short boat ride or car ride from all the things the area has to offer. Don’t forget to visit the Yerkes Observatory during your stay. The same firm that created New York’s Central Park created the lush grounds surrounding the 125-year observatory, which offers beautiful pictures day and night, inside and outside. 

READ MORE: These Wisconsin Towns Named Among America’s ‘Most Beautiful’


CATEGORIES: Uncategorized


Local News

Related Stories
Share This