Four of Our Favorite Wisconsin Main Street Communities

Discover Wisconsin

March 15, 2019

A community’s Main Street is the beating heart of its town. It’s the city’s center, it’s full of history, and it’s a gathering spot for residents and visitors alike. In Wisconsin, Main Street communities are known for being friendly, charming and authentic, with unique personalities that set them apart from one another. And sometimes, the greatest adventures to be had are found just off Main Street, on the surrounding trails, rivers, lakes and roads. Here are four Wisconsin Main Street Communities that our crew loves to visit.


Just minutes from Oshkosh, on the banks of the Fox River, is the city of Omro. Omro is a quintessential Wisconsin Main Street community with a rich history, small town pride, and lots of opportunities to get out and explore. A free, self-guided historical walking tour is a great way to start your visit, and get acquainted with downtown. Omro also has fantastic parks where they hold a variety of fun community events throughout the year, including their big Fourth of July Celebration at Scott Park. Nearby Terrell’s Island on Lake Butte des Mort is also a fantastic place to hike, bike, and enjoy beautiful scenery and wildlife. Omro is a small town, but it has big city amenities and lots of ways to enjoy the outdoors – what more could you ask for in a Wisconsin vacation?


Just miles away from the Kettle Moraine State Forest in Southeast Wisconsin, set in a landscape rich with lakes, hills and prairies, is the city of Whitewater. Home to the University of Wisconsin Whitewater, the city has a lively, family-friendly, urban feel, but it’s also steps away from country roads, and vast outdoor spaces, including a beautiful portion of the Ice Age Trail. Residents and visitors can take advantage of fantastic local shops and restaurants, fun community events like the weekly City Market, as well as countless opportunities for outdoor recreation. It’s one of Wisconsin’s biggest little cities, and it has a little of everything you need for the perfect getaway!

Florence County

Deep into the Northwoods, where Wisconsin’s border meets Michigan’s Upper Peninsula, is Florence County. More than 50 percent of the land in Florence County is publicly owned, making it a haven for those looking for outdoor recreation and undisturbed wilderness. In addition to a lively downtown and charming B&Bs, visitors can take advantage of 265 lakes, breathtaking waterfalls, Wisconsin’s two original wild rivers, and miles of forested trails to hike, bike, ATV, horseback ride, cross country ski, snowshoe and snowmobile. The beauty and wildness of Florence County will make you feel like you’re a world away, but it’s right here in Wisconsin!


Osceola, located on the St. Croix National Scenic Riverway, is a cool little river town with lots of history, natural beauty, and friendly folks. Its historic Main Street is lined with charming shops and eateries, and a gorgeous waterfall sits at the center of town. Located less than an hour from the Twin Cities, Osceola offers a perfect balance of recreation, business and tourism. Visitors looking to be outside can enjoy miles of hiking and biking trails, paddling on the scenic St. Croix River, year-round activities at Trollhaugen Outdoor Recreation Area, and nearby Interstate State Park. With so many ways to relax, rejuvenate and connect with nature, it is the ultimate small-town getaway!
What are your favorite Main Street communities here in Wisconsin? Let us know in the comments below! And learn more about all of these destinations in our “Just Off Main Street” episode of Discover Wisconsin.
Jessica Murphy is a producer of Discover Wisconsin. Watch the show on Fox Sports Wisconsin every Saturday at 10am or on Roku, Chromecast, Smart TV, Amazon Fire, and Apple TV.

You May Also Like…