Aerial View of Downtown Janesville, Wisconsin during summer.

The Best Small Towns To Retire In Wisconsin

One of the pillars of the Midwest, Wisconsin is famous for its diverse and beautiful geography, delicious dairy products, and the kind of midwestern charm known throughout the country. For seniors and retirees looking for a comfortable and affordable place to retire, the cities, towns, and villages of Wisconsin offer all and more that anyone could ask for. Cities like Milwaukee and Green Bay can provide urban life and professional sports while the state is full of quaint villages ripe for small-town life. However, if it is a natural beauty and the outdoors you are searching for, these six Wisconsin towns can provide it in spades. Fishing, boating, hiking, and biking are among only a few of the outdoor activities these communities offer, as well as the culture and history that comes with living in the heartland of the United States.

Appleton

Aerial view of Lawrence University, Appleton Wisconsin
Lawrence University, Appleton Wisconsin.

Located on the Fox River and just 30 miles from Green Bay, Appleton is the sixth-largest city in Wisconsin. With a population of 75,000, it offers a perfect mix of small-town charm and urban amenities. The city is also renowned for its fishing opportunities; the Fox River has produced numerous state records, including for striped bass and shortnose gar. But outdoor recreation goes beyond fishing—many paved trails run along the river, ideal for hiking, biking, or skating, and there are unpaved trails suitable for horseback riding. Nearby, Lake Butte des Morts provides excellent fishing in summer and ice fishing in winter, with numerous trails around it for land-based activities. Combining outdoor adventures with city amenities and attractions like The History Museum at the Castle makes Appleton a wonderful place to live.

Janesville

Riverfront and buildings in Janesville Wisconsin
Riverfront Janesville, Wisconsin.

If you want a similar vibe to Appleton but also want to stay close to the Illinois border for travel and tourism, Janesville is the place to visit. A city of 65,000 residents, Janesville offers many exciting outdoor activities. The Rock River cuts through the city as it flows, providing great opportunities for fishing, water sports, and paddle sports. There is also a well-developed system of paved trails along the river. For hikers, the Sugar River State Trail offers beautiful views that showcase both Wisconsin's natural beauty and rail history. For those seeking a vibrant urban hub to explore the outdoors, Janesville is the right choice.

Baraboo

Baraboo, Wisconsin, Ringling Theater exterior, named for the home of the Ringling Brothers Circus
Baraboo, Wisconsin, Ringling Theater. Image credit lynn friedman via Shutterstock

For a more small-town feel, Baraboo is a great destination. With the Baraboo River flowing through the town and a wide variety of natural landmarks in the surrounding area, it is a perfect place for anyone who loves the outdoors. The Baraboo River offers excellent fishing, and nearby is the Elroy-Sparta Bike Trail for hiking, biking, and skating. Just south of town is Devil's Lake State Park, the largest state park in Wisconsin. It features beautiful rock formations, glacial features, hiking and biking trails, campsites, rock climbing spots, and a sledding hill. There are also several Native American burial grounds. Another great park near Baraboo is Pewit's Nest State Natural Area, which offers stunning views of Wisconsin's glaciated landscape. These natural attractions, combined with the warm Midwest charm of Baraboo, make it a wonderful place to call home.

Sturgeon Bay

An image of steel bridge and boats located in historic Sturgeon Bay located in Door County Wisconsin
Sturgeon Bay in Door County Wisconsin.

For those who want to live lakeside on Lake Michigan, Sturgeon Bay is the place to be. The largest city on the Door Peninsula that extends into Lake Michigan, a population of just over 9,500 gives the town a great small-town feel. For anyone who loves boating, this is a fantastic spot. The town has a port on Sturgeon Bay, the water feature from which the town gets its name. Recreational boaters will enjoy easy access to the lake, while those who love fishing can find spots along the shoreline or take a trip out onto the bay. There are also recreational cruises departing from the docks, sailing around Sturgeon Bay. For those interested in the maritime industry, Sturgeon Bay is a perfect place for ship spotting, as the Sturgeon Bay Ship Canal runs right through the area. If you're not as interested in spending time on the water, Potawatomi State Park offers stunning scenery and amenities for hiking, biking, snowmobiling, fishing, and canoeing. With many Native American historical landmarks in the area, Sturgeon Bay is a wonderful place to call home for water enthusiasts.

Grafton

Aerial view typical suburban street. Residential houses, agricultural field from above. Autumn Fall scenery, Rural landscape. Grafton, Wisconsin
Farmlands and homes in Grafton, Wisconsin.

A small town rich in local history, Grafton appeals to history buffs of all kinds as well as outdoor enthusiasts. With just over 12,000 residents, this charming town offers a true Midwestern atmosphere. The Ozaukee Interurban Trail winds through the town and extends into the countryside and wilderness, making it perfect for hiking, biking, spotting wildlife, and admiring the glaciated plain where Grafton is located. The Milwaukee River also flows through the town and is ideal for fishing. In addition to its natural beauty, Grafton boasts many historic sites, including remnants from the early colonial period such as the lime kilns of the Milwaukee Falls Lime Company and the Grafton Flour Mill. There are also several historic spots associated with Paramount Records, a major record company known for producing African American music in the early 20th century.

Elroy

Buildings in downtown Elroy, Wisconsin.
Downtown Elroy, Wisconsin.

If even towns like Sturgeon Bay or Grafton seem too big, then Elroy is the place to visit. With a population just under 1,500, peace and quiet abound. Located in the western plains of the state, Elroy offers plenty of outdoor activities despite its small size. The Elroy-Sparta State Trail runs right through town—a paved path for hiking, biking, and skating. This trail is also a rail trail, following the route of an old railway, so there are tunnels you can walk or bike through. Nearby, the 400 State Trail is available for hiking, biking, snowmobiling, and horseback riding. Both the Elroy-Sparta and 400 State Trails pass historic sites and connect to other trail systems, letting dedicated bikers and hikers travel many miles.

Wisconsin is a great place to travel and an even better place to retire to, especially if the outdoors and natural beauty are important parts of your life. Whether it is boating on the bay, fishing in a river, or hiking through a glaciated plain, Wisconsin has it all and its cities are all great hubs to explore this heartland of the Midwest.

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