Oconomowoc, Wisconsin: Veterans of foreign wars of Oconomowoc community held a memorial veterans day parade, via Aaron of L.A. Photography / Shutterstock.com

8 Towns Perfect for Retirement in Wisconsin

The prospect of starting a new life after retirement brings a smile to most career professionals. Retirement is an opportunity to finally rest after years of toiling a 9 to 5, adopt new hobbies, and set out to explore interests kept at bay due to work obligations. Where you choose to settle greatly influences the enjoyment of this celebratory season. Wisconsin presents many charming small-town options with a high quality of life and manageable cost of living.

From lakefront enclaves to historic downtowns and scenic countryside havens, each of these rural communities offers various cultural activities, recreational opportunities, and a tight-knit small-town vibe retirees find most alluring. If you are contemplating retirement in Wisconsin, these understated gems present the perfect setting to relax and reap the rewards of all those working years.

Mount Horeb

Mount Horeb Opera Block, Wisconsin
Mount Horeb Opera Block, Wisconsin, By Jaknelaps - Own work, CC BY-SA 3.0, Wikimedia Commons

The "Mustard Capital of the World," as it's popularly known to the locals, is a charming retirement community where the elderly can lead a peaceful lifestyle. Mount Horeb provides a mix of attractions to keep retirees entertained - no matter their preferences. Newcomers may fancy a tour of the Driftless Historium & Mount Horeb Area Historical Society for a glimpse into the region's heritage.

The downtown district impresses with an assortment of restaurants, antique shops, boutiques, and pubs, culminating in an inviting social setting. The Brix Cider provides a family-friendly atmosphere for seniors to link up with peers over a wholesome meal. However, when it comes to outdoor recreation, Donald County Park hosts 775 acres of nature areas with opportunities for hikers, campers, and sightseers. Finally, Mount Horeb has a median home price of $474,500.

Port Washington

Port Washington Town view in Wisconsin
Port Washington Town view in Wisconsin

Situated on the scenic shores of Lake Michigan, Port Washington provides a cozy waterfront setting for seniors to enjoy a laid-back retirement. There are numerous opportunities for ardent outdoorsmen in this Ozaukee County community, which encourages an active lifestyle. Port Washington South Beach Park is a local favorite and features a sandy slice of beach overlooking Lake Michigan, ideal for summer picnics. Also, Port Washington Avian Sanctuary's secluded environment is tailored for long walks while staking out the different bird species that call it home.

Retirees can also take advantage of sailing opportunities provided by different local outfitters. Those who enjoy fishing can hire a vessel from Angry Fin Charter Fishing for a remarkable excursion on the calm lake waters. Because of its proximity to Milwaukee, the real estate prices in Port Washington are understandably above the state average at $530,000.


Aerial View of the Madison Suburb of Waunakee, Wisconsin
Aerial View of the Madison Suburb of Waunakee, Wisconsin

Waunakee promises retirees the best of both worlds, balancing between a serene rural atmosphere and access to big-city amenities. The town is less than 30 minutes from Madison, granting seniors ready access to an array of superior recreation and health facilities in the state capital. However, this has increased the price of homes in Waunakee, with the average at around $600,000. There are dozens of opportunities for those who enjoy the outdoor lifestyle, especially across the 422-acre Governor Nelson State Park. These range from fishing and boating to lakefront picnicking.

Meanwhile, relaxed tee time with friends at the Meadows of Sixmile Creek is a go-to activity for seniors seeking recreation in Waunakee. The town also hosts a couple of fitness facilities pensioners can utilize to stay ahead of their physical health, including Fortify Fitness Collective.


WIS 32 in Caledonia, Wisconsin at 4 Mile Road
WIS 32 in Caledonia, Wisconsin at 4 Mile Road

Caledonia allows retirees to enjoy the perks of living in a small town, which include an affordable lifestyle, with a median housing cost of $392,900. Fresh residents looking to get acquainted with the heritage of their new home can visit the Caledonia Historical Village, which displays a range of archives, artifacts, and relics telling the history of the town. There are a couple of cozy outdoor spaces that call for friendly social gatherings in Caledonia. Witt's End is an excellent example and features a serene atmosphere near Little Gillet Lake, where seniors can meet up with peers over a glass of beer.

Thanks to Parkview Senior-Living Community in Caledonia, retirees benefit from multiple senior-based facilities, including affordable housing, independent-living apartments, and a world-class memory-care facility. The campus also organizes various programs to make for a vibrant and active senior lifestyle.

Sheboygan Falls

Downtown Sheboygan Falls, Wisconsin
Downtown Sheboygan Falls, Wisconsin, By Royalbroil - Own work, CC BY-SA 3.0, Wikimedia Commons

If you see yourself settling in a quiet and pocket-friendly river town for retirement in Wisconsin, Sheboygan Falls is an excellent choice. This likable community sits on the scenic banks of the Sheboygan River, with around 9,000 people calling it home. It has enough room in the open spaces for retirees to comfortably indulge in outdoor recreation, such as playing golf at Bull at Pinehurst Farms Golf Course. The town hosts the Sheboygan County Memorial International Airport, making it easy for seniors to get to neighboring towns in search of further leisure opportunities and superior medical facilities.

On the airport grounds sits the Aviation Heritage Center of Wisconsin, which delights aircraft enthusiasts with an interesting collection of related exhibits. Sheboygan Falls also presents pensioners with a budget-friendly route to owning a retirement home, considering that the average cost of real estate is only $374,900.


First Congregational Church of Hartland
First Congregational Church of Hartland, By Shadowe - Own work, CC BY-SA 3.0, Wikimedia Commons

Hartland is an adorable river town and suburb of Milwaukee. It harbors a tiny community of just above 10,000 and offers a relaxed rural atmosphere. Despite its small population, Hartland is jam-packed with an array of experiences to keep pensioners engaged. Those who frequently get visited by their grandkids will appreciate the presence of the Lake Country Rotary Splash Pad. The venue is perfect for spending quality time with family, providing a range of kid-friendly amenities, including a splash pad, water play equipment, and picnic areas.

Whether a fan of the arts or not, watching a live performance at the Lake Country Players is a popular local pastime that allows new retirees to mingle with residents, and potentially establish lasting connections. Also, signing up for a membership at the Legend of Bristlecone Country Club offers access to diverse recreation facilities, including a beautiful golf course. Considering everything Hartland has to offer, it is no surprise that the average cost of a home is a little steep at $684,900.


Beautiful aerial shot of a church on a peninsula in Oconomowoc, Wisconsin.
Beautiful aerial shot of a church on a peninsula in Oconomowoc, Wisconsin.

Oconomowoc's unique name was derived from the Native Potawatomi tribe's term, which translates to "waterfall." The town is surrounded by the glistening waters of Lake Fowler, beckoning retirees to step outside into a range of recreations. The lake delights with generous angling opportunities, thanks to the sizable population of panfish, walleye, northern pike, and largemouth bass. Retirees can look forward to exciting dining experiences whenever they opt to eat out - given the array of eateries within Oconomowoc. Options range from Lago Su Bella to Lucky Chucky's Beach Bar & Grill, and both offer a comfortable atmosphere with lovely views.

With the Oconomowoc Community Center, pensioners can make the most of inviting opportunities to socialize and get acquainted with the other residents. The venue boasts serene lakefront scenery for relaxation. If you are planning to buy a home, the average listing price in the town is $599,000.


Aerial view of downtown Cedarburg Wisconsin known for its quaint downtown district lined with historic buildings.
Aerial view of downtown Cedarburg Wisconsin known for its quaint downtown district lined with historic buildings.

A mix of rich history, unique culture, and small-town charm entices fresh retirees to settle in this beautiful Ozaukee County village. Cedarburg is known for its impressive historic district, home to multiple structures listed on the National Register of Historic Places. A visit to Cedarburg History Museum offers new residents a chance to explore their hometown’s history, from its founding in the 1800s. The town center maintains a vibrant personality with several attractions worth checking out. Cultural vultures should consider visiting the Cedarburg Art Museum, or the Cedarburg Cultural Center, to sample a piece of local heritage.

Cedarburg also houses a vibrant brewery and winery scene, with several establishments offering remarkable tasting experiences. At the Cedar Creek Winery downtown, pensioners can taste award-winning wines, from fine whites to robust reds. Although the median home cost is over the United States average at $524,800, there is value for money when investing in one.

Final Thoughts

Whether you are looking for a slow pace of life amidst rich natural surroundings, cultural activities in historic districts, or a supportive community to join for your retirement in Wisconsin, the above small towns make ideal spots to embark on a new chapter - with more leisurely days. Their scenic settings paired with a welcoming local spirit foster the kind of lifestyle where true rest and recreation take priority. Taking the time to explore the many fulfilling options the Badger State has to offer is guaranteed to lead retirees towards a special living space to comfortably unwind and live their golden years to the fullest.

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