Great Spots for Snowmobiling Near Chicago

When winter rolls around, nothing compares to hitting the open trails under an expansive sky or through scenic forests with good friends. You may not know it, but a thrilling snowmobiling experience is a short, easy drive across Wisconsin’s southern edge. Check out some great snowmobiling spots near Chicago to make special memories with your crew this season.

Cheese Country Recreation Trail

Monroe, the Swiss Cheese Capital of the USA, is also the starting point to this 47-mile trail that extends through rolling hills and open farmland. As a former railroad bed, the route crosses several vintage trestle bridges and passes through a number of old mining towns that have since grown into charming spots with unique attractions.

Unload at the free park-and-ride in Monroe before sledding through the snow-covered Wisconsin landscape to the trail’s end in Mineral Point. There, you and your crew can refuel with some tasty cuisine from the appetizing menu at Midway Bar & Grill. When you return to Monroe, be sure to grab some famous curds to go at the Swiss Colony Outlet Store and finish your day with some relaxing sips together at the Minhas Craft Brewery, the Midwest’s oldest continually operated brewery.

Walworth County Trails

You may be familiar with Lake Geneva’s resort reputation, but did you know Walworth County is also home to a total of 350 miles of beautiful snowmobile trails? Since 1970, 14 dedicated snowmobile clubs have committed to providing snowmobilers with some of the finest wooded and wetland trails in the area. The 12-mile White River State Trail from Elkhorn to Burlington gives riders a scenic journey through picturesque towns, historic bridges, scenic vistas and other magical sights.

When you and your friends need to warm up, stop in at Lake Lawn Resort to relax at the spa and get a good night’s sleep. For dinner, try the classic Wisconsin supper club fare from the Mars Resort and Restaurant, where your group can dine in an illuminated igloo on the patio.

Glacial Drumlin State Trail

This 52-mile stretch nestled between Madison and Milwaukee takes you through a serene landscape created by the last ice age. Located on the fringes of the Kettle Moraine State Forest, snowmobilers are greeted with regular sightings of deer, foxes, cranes and turkeys that call the unique geographical formations their home.

In total, the trail passes through 10 small towns with no shortage of pleasant attractions. In Lake Mills, about halfway through the trail route, stop at Doyle’s Dogs for a quick bite. Or, go a little further and stop in Delafield to explore your choice of coffee houses, breweries and fine dining options including Zin Uncommon California Italian on Main Street.

Racine and Kenosha County Trails

Just beyond the state line in Wisconsin’s southeasternmost corner lie Kenosha and Racine counties. 19 snowmobile clubs tend 312 trail miles through wide-open farm country and scenic wooded areas in a region that receives around 50 inches of snow annually. Only around an hour from Chicago, these trails are perfect for a quick winter getaway with family and friends.

If you’re looking for a break while in Racine County, grab a delicious kringle at O&H Danish Bakery or stop for a warm beverage at The Coffee House at Chestnut and Pine.

Check the trails before you go with the Wisconsin Snow Report and browse our snowmobiling directory for more helpful tips!