8 Oldest Founded Wisconsin Towns to Visit in 2024
With a rich history stretching back to territorial days, Wisconsin allows visitors to step back in time by exploring some of its earliest established communities. From ports along mighty Lake Michigan to crossroads settlements in the southern grasslands, these adorable communities have maintained much of their historic structures and atmospheres while embracing modern progress. Touring them rewards explorers with an intimate look into how the Badger State was developed and cultivated local heritage.
The quiet streets of these destinations, lined with buildings dating back over a century, hint at the people and events that shaped Wisconsin. The following old towns to visit in Wisconsin demonstrate rustic charm with their well-preserved old-world architecture and cultural lessons in Midwestern history.
Prairie Du Chien
Prairie du Chien is one of the oldest colonial settlements in the Midwestern United States, settled by French voyageurs in the late 17th century. The town is laden with historic sites as proof of its longstanding heritage, none more appealing than the Villa Louis Historic Site. A National Historic Landmark, this well-preserved Victorian estate features a gorgeous mansion overlooking the Mississippi River. Prairie du Chien has the Fort Crawford Museum to show its military history. The United States Army occupied the outpost in the early to mid-19th century, home to several sites and monuments from the period.
While exploring the town's history, you can use the opportunity to revel in the lovely outdoors of St. Feriole Island Park. This historic park hosts numerous amenities, from picnic tables to ball fields, with a serene setting on the banks of the Mississippi River.
Milton
Milton traces its beginnings to 1838, when Joseph Goodrich founded the town. Situated approximately 70 miles from Milwaukee, this town is an exciting destination for travelers seeking a break from the busy city. The town has a colorful history that is well-captured inside the Milton House Museum. Inside this iconic venue lie loads of old artifacts highlighting Milton's history, including its role during the Underground Railroad. Several outdoor spaces in the town allow for multiple recreation opportunities. Golf lovers have the Oak Ridge Golf Course to indulge in their favorite pastime.
A few watering holes in downtown Milton invite tourists to sample locally crafted wines and brews. After a long day exploring the regions, you can relax and unwind with a beer bottle at Junction Pub.
Pepin
Pepin dates back to the mid-19th century and boasts a lovely setting on the shores of Lake Pepin. The town is famous for being the home of Laura Ingalls Wilder, whose endearing legacy is preserved at the Laura Ingalls Wilder Museum. You can learn more about Pepin's history at the Pepin Depot Museum, which harbors an exhibit collection chronicling the town's railroad and steamboat heritage.
Those who want to test the waters of Lake Pepin can head to the Pepin Marina and hire a vessel for an easygoing sail. Alternatively, you can book a tour with Cruise Pepin for a remarkable experience from the water with a unique perspective of the town. When you need something to eat, Homemade Cafe serves delicious American fare that promises to please your taste buds.
Mineral Point
Mineral Point experienced a mining boom that attracted Cornish prospectors in the 1800s. At its peak, it was among the nation's most lucrative lead and zinc mining centers. Today, vacationers tour the Mineral Point Railroad Museum to explore local history, focusing on the vital role played by the railroad in transporting mineral ores. The town provides a window to its storied past at Pendarvis, listed on the National Register of Historic Places. The site hosts historic structures built by Cornish immigrants.
Over the years, the community has adopted a rich arts culture, enabling enthusiasts to enjoy exciting live performances at the historic Mineral Point Opera House. The same applies to the Shake Rag Alley Center for the Arts, which focuses on the visual arts.
Portage
Portage was a vital overland linking the Wisconsin and Fox Rivers on a route used by Native Americans and European explorers. The town has a lovely historic district harboring some of its best-kept secrets from the past. Strolling through the neighborhood reveals treasures like the Historic Indian Agency House, built in 1832, which stores memories of a landmark period in the Midwest. The Fort Winnebago Surgeons Quarters is another nationally registered historic location with two vintage structures dating back to the 19th century.
Visitors will find numerous archives, photographs, and artifacts inside the Portage Historical Society Museum, which has all the necessary information for a broader glimpse into local history. Beyond the history, you can find a serene spot to relax and enjoy nature at Pauquette Park.
De Pere
One of the most exciting small towns to visit in Wisconsin, De Pere's rich heritage started with the French explorers who navigated its waterways in the 17th century. The town provides direct access to the Fox River and Green Bay, culminating in exquisite natural scenery. Strolling along the De Pere Riverwalk and Wildlife Viewing Pier puts you in the perfect position to soak in the fantastic scenery that defines De Pere's outdoors. A charming arts and culture scene in De Pere allows connoisseurs to have fun at the Mulva Cultural Center.
Meanwhile, fans of the silver screen can look forward to a fulfilling movie experience at De Pere Cinema, which screens the latest Hollywood releases. After exploring the town, you can settle down at Cocoon Brewing and enjoy a glass of locally-produced beer.
Cassville
This quaint Mississippi River community blends picturesque natural landscapes with captivating history for an unforgettable tourist experience. Cassville traces its beginnings to the 1800s and presents a glimpse into its formative years at the Stonefield Historic Site. This site features a reconstructed old farming village with structures like a jail, saloon, farmhouse, and schoolhouse, just as it was in the past.
A short distance from the farming village, the Nelson Dewey State Park beckons adventurers to discover the beauty of Cassville's backcountry. Spanning over 700 acres along the scenic Mississippi River, this vast wilderness area offers recreational opportunities such as boating, fishing, hiking, and camping. When you are tired from the park's countless adventures, you can head back downtown and enjoy a nice cocktail at Son Chasers Social Club before retiring for the night.
Sheboygan
The new meets the old in this lovely Great Lakes town in Sheboygan County. It was incorporated in 1846 and boasts a fascinating heritage that guests can get familiar with inside the Sheboygan County Museum. This historical venue leaves first-timers in awe of its underground gallery chronicling the region's heritage. Sheboygan is recognized around the county as a bustling arts and culture hub, evidenced by the multiple world-class art centers it hosts. The John Michael Kohler Arts Center is an excellent example, a celebrated center for visual and performing arts.
When you are not reveling in Sheboygan's rich heritage and thriving arts, you can head to the Kohler-Andrae State Park to experience its natural beauty. While there, you can access sandy beaches that are ideal for picnicking and camping in a cozy setting.
Exploring these living snapshots of Wisconsin's territorial days and early growth gives visitors an intimate sense of history and a fresh perspective on how the Badger State came to be. It is an opportunity to discover preserved architectural gems and cultural traditions, ensuring memorable lessons off the beaten path. If you are up for an immersive historical experience during your Midwest travel itinerary, any of these small towns to visit in Wisconsin promises to leave a lasting impression.
