Classic Toyota’s Guide to Winter Fun in Illinois and Wisconsin

Jan 26, 2022

We’re back with another great guide to Winter Sports fun in Illinois and Wisconsin. Check out our latest travel blog and get to planning your great winter escape outdoors with some of our great picks for destination getaways and day trips. From snowmobiling to snow tubing to ice skating and more, there’s lots of fun for everyone!

Minocqua Forest Riders Snowmobile Club

This incredible group maintains over 160 miles of trails in Northern Wisconsin in the Minocqua area. The group grooms the trails weekly, ensuring they’re in prime condition for weekend activities. You can view the full map of trails here! There’s a lot of additional wintertime Northwoods activities in the area, too: ice skating, ice fishing, snowshoeing, skiing, and sledding galore! There’s even snow tubing and an incredible winter zipline course.

Where to Eat: Northfork Fin & Filet in Arbor Vitae WI; Mary’s Place North in Arbor Vitae WI; Mavericks Restaurant Mexicano in Woodruff WI; Black Bear Bar and Grill in Minocqua WI; Great Northern Coffee Traders in Minocqua WI; Minocqua Prime in Minocqua WI; Lakeside Grill in Minocqua WI; Dixies Coffee House in Manitowish Waters WI

Where to Stay: Timber Bay Resort in Lac du Flambeau; Pointe Hotel & Suites and Conference Center in Minocqua; Pine Hill Resort in Minocqua; The Waters of Minocqua; Whitehaven Bed & Breakfast in Minocqua Winter Park

Other Activities Nearby: The Northwoods Petroleum Museum, Rhinelander Logging Museum, Three Lakes Center for the Arts, Campanile Center for the Arts, Island City Antique Market

Bearskin State Trail

This 26 mile trail stretches through two counties in Wisconsin. You’ll enjoy activities all year round such as walking or biking and fishing in the warmer months, and snowmobiling and cross country skiing in the winter time. Enjoy beautiful views of densely wooded pine forests, and enjoy the many lakes and ponds inviting you to enjoy the sites and sounds of the majestic regional wildlife.

Where to Eat: Shady Sue’s Restaurant, Rhinelander Family Restaurant, Joe’s Pasty Shop, Big Daddy’s, Pat’s Tavern & Grill, Crimson Cafe, Dina Mia Pizza, CT’S Deli LLC

Where to Stay: Quality Inn, Days Inn & Suites, AmericInn by Wyndham, Clear Lake Inn and Resort, Holiday Acres Resort on Lake Thompson, Centerstone Resort Lake-Aire-Tomahawk, Kafka’s Resort

Other Activities Nearby: The Hodag, ArtStart, Rhinelander Historical Society

Des Plaines River Trail Wadsworth

Spanning a whopping 56 miles in both Cook and Lake counties, this gorgeous trail is perfect for year round fun. You can enjoy mountain biking, hiking, walking, and horseback riding in warmer weather, or head out for a cool afternoon of winter fun with cross country skiing or snowmobiling. This trail winds its way along protected lands and 85% of the river running through Lake County. Enjoy all of the sights and sounds of nature and do a little bird watching or wildlife photography while you’re out there!

Where to Eat: The Shanty Restaurant in Wadsworth; Captain Porky’s in Wadsworth; The Duck Inn in Wadsworth; Mama K’s Pizza and Grille; Pho Kho Gia Lai Vietnamese, Wildberry Pancakes and Cafe in Libertyville; Madras Kafe in Vernon Hills; Nirvana Wine & Grillerie in Vernon Hills; Tsukasa of Tokyo in Vernon Hills

Where to Stay: The Lotus Suites, Dragonfly Bed and Breakfast, The Inn on Sheridan, Great Wolf Lodge Water Park Illinois

Other Activities Nearby: 60 to Escape; Funflatables Gurnee; Extreme Flight Simulation; Van Patten Woods Forest Preserve; Midlane Country Club, Russell Military Museum

Lakewood Forest Preserve in Wauconda

Whether you’re heading out for a solo day to get in touch with nature, or breaking away from the screens with your family and friends for outdoor fun, you’ll have a blast here in the Wauconda area. From Ice Fishing to Ice Skating to Sledding and Snowmobiling, there are plenty of ways to enjoy wintertime outdoors at the Lakewood preserve. There are even several dog parks for your canine companions to enjoy a little socialization time!

Where to Eat: SLYCE Coal Fired Pizza Company; Bulldogs Grill; Uncle D’s Bar and Grille, Strawberry Moon; ALonso’s Burrito Express; Whisk Bakery & Coffee; Deacon’s Restaurant & Bar at the Golf Farm; Sofia’s Mexican Restaurant

Where to Stay: Victoria Rose Garden Bed & Breakfast; Waterfront Hotel & Marina; Lincolnshire Marriott Resort; The Cottages on Petite Lake; The Mansion Bed & Breakfast; Cypress Resort & Marine

Other Activities Nearby: Wauconda Bowl, Silver Lotus Yoga, Wedgewood Riding Center; Nippersink in Volo; Side Lot Brewery ; Avolve Fitness