Best Scenic Winter Drives in the Midwest

The Midwest transforms into a winter wonderland when snow blankets the rolling hills, frozen lakes, and charming small towns. Whether you’re looking for peaceful countryside drives, stunning frozen waterfalls, or breathtaking national parks covered in snow, these scenic routes are among the best winter getaways in the Midwest and will take your winter road trip to the next level.
Here are the top five best scenic winter drives in the Midwest that offer beautiful winter landscapes, snowy adventures, and unforgettable views.
These drives also offer excellent winter vacation ideas for families and adventurers alike.

Route: U.S. Highway 61 (Runs along the Mississippi River)
Why It’s a Must-Drive in Winter: The Great River Road is an ideal winter vacation route, following the Mississippi River through four Midwest states, offering snow-covered bluffs, frozen riverbanks, and charming river towns.
Best Winter Stops Along the Route:

• Galena, Illinois – A historic town with festive winter lights and cozy small-town charm.
• Pikes Peak State Park, Iowa – Overlooks the Mississippi River with scenic winter views.
• Wabasha, Minnesota – Visit the National Eagle Center to see bald eagles in their winter habitat.
• La Crosse, Wisconsin – Enjoy snowy riverfront parks and holiday markets.

Travel Tip: Drive safely as winter storms can cause icy roads near river valleys. Check weather conditions before starting your journey.

Route: Highway 42 & 57 (Sturgeon Bay to Gills Rock, Wisconsin)
Why It’s a Must-Drive in Winter: Nicknamed the “Cape Cod of the Midwest,” Door County is one of the best winter getaways in the Midwest, with frozen shorelines, ice caves, and festive small towns.
Best Winter Stops Along the Route:

• Peninsula State Park – Perfect for snowshoeing and frozen bay views.
• Cave Point County Park – Watch Lake Michigan waves crash against ice-covered cliffs.
• Baileys Harbor & Fish Creek – Cozy towns with holiday lights and scenic frozen harbors.
• Washington Island – Take the ferry to an island covered in sparkling snow.

Travel Tip: Check ice conditions before exploring frozen caves or venturing onto the lake.

Route: Highway 92 & County Roads (Madison County, Iowa)

Why It’s a Must-Drive in Winter: This peaceful rural drive takes you through Iowa’s famous covered bridges, which look even more magical when dusted with snow.
Best Winter Stops Along the Route:

• Hogback Covered Bridge – One of Madison County’s most scenic historic bridges.
• Roseman Covered Bridge – Featured in The Bridges of Madison County.
• Winterset, Iowa – A charming small town with holiday decorations and cozy diners.
• Pammel State Park – Offers snowy woodland hikes and wildlife spotting.
• Medora, North Dakota – A gateway to Theodore Roosevelt National Park, perfect for watching wild horses and backcountry skiing.

Travel Tip: Watch for deer crossings, especially at dawn and dusk.

The Midwest is a treasure trove of winter adventures, offering a wide range of activities and events perfect for families, couples, and solo travelers. Here are some popular winter activities and events to consider:

• Cross-Country Skiing: Glide through the beautiful winter landscapes of Wisconsin, Michigan, and Minnesota on numerous cross-country skiing trails.
• Ice Fishing: Try your luck at catching fish through the ice on Lake Michigan, Lake Superior, or one of the many smaller lakes in the region.
• Dog Sledding: Experience the thrill of dog sledding through the snowy terrains of Wisconsin, Michigan, or Minnesota.
• Winter Festivals: Attend festive events like the Winter Festival in Madison, Wisconsin, or the Winter Carnival in Traverse City, Michigan, featuring ice skating, snowshoeing, and live music.
• Snowshoeing: Explore the serene winter landscapes on snowshoes, with trails available in Wisconsin, Michigan, and Minnesota.
• Ice Skating: Enjoy ice skating at outdoor or indoor rinks, such as the famous ice rink in Millennium Park, Chicago.
• Winter Sunrise: Wake up early to witness the stunning winter sunrise over Lake Michigan or Lake Superior, a truly magical experience.
• Winter Wonderland: Discover the beauty of the Midwest’s winter wonderland, with parks and nature reserves offering scenic hiking trails and breathtaking views.
• Country Skiing: Experience the thrill of country skiing through the snowy landscapes of Wisconsin, Michigan, or Minnesota.

Popular Winter Events:

• The Winter Festival in Madison, Wisconsin: A fun-filled festival featuring ice skating, snowshoeing, and live music.
• The Winter Carnival in Traverse City, Michigan: A festive event with ice skating, snowmobiling, and live music.
• The Chicago Winter Festival: Enjoy ice skating, snowshoeing, and live music in the heart of the city.
• The Door County Winter Festival: A festive event featuring ice fishing, dog sledding, and live music.
• These activities and events showcase the Midwest’s vibrant winter culture, offering something for everyone, whether you’re seeking adventure, relaxation, or a fun day out with family and friends.

Before hitting the road, follow these winter safety tips for a smooth and stress-free drive:

• Check the weather forecast before traveling.
• Drive slowly and increase your following distance on icy roads.
• Use winter tires for better traction.
• Pack an emergency kit with blankets, snacks, and a flashlight.
• Fill up your gas tank before heading into rural areas.
• Stay updated on road closures by checking state transportation websites.

Need a winter-ready vehicle? Find an SUV with all-wheel drive or a truck with four-wheel drive to handle Midwest road conditions with ease.

The Midwest offers some of the best winter vacation ideas with its picturesque winter drives, from lakefront highways to snowy backroads lined with historic bridges. Whether you’re chasing frozen waterfalls in Minnesota, driving along icy shorelines in Michigan, or exploring festive small towns in Wisconsin, these routes promise unforgettable winter scenery.
Where to Start

• Choose a scenic drive that fits your adventure style.
• Check road conditions and pack winter gear.
• Plan stops at cozy winter lodges, frozen lakes, and national parks.
• Enjoy the snowy landscapes and stunning Midwest beauty.

Looking for the perfect road trip vehicle? Visit a local dealership to test drive an AWD or 4WD SUV today and make your Midwest winter road trip safe and comfortable.