Discover the Driftless: 6 Best Weekend Getaways in the Midwest

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Discover the Driftless: 6 Best Weekend Getaways in the Midwest

When I first heard the phrase “the driftless,” I imagined it referred to the people who live near the Mississippi River in the Midwest as much as it did the landscape they inhabit. Why would you drift from the rivers, streams, waterfalls, and bluffs that invite you to admire their beauty and explore their woods and wildlife? 

Believe it or not, it’s actually named after the glaciers that didn’t drift. Thousands of years ago, glaciers covered much of North America. They smoothed and flattened the land, leaving silt, gravel, and rock behind. But the glaciers didn’t cover approximately the 24,000-square-mile expanse now known as the Driftless Area. 

Characterized by a steep, rugged landscape, and the largest concentration of cold water streams in the world, the Driftless hugs the Mississippi River through Minnesota, Wisconsin, Iowa, and Illinois. 

Nestled within the rolling hills and picturesque valleys of the Driftless Area lie quaint towns brimming with history, culture, and natural beauty. From the vibrant streets of Galena, Illinois, to the serene landscapes of Decorah, Iowa, each destination offers its own unique allure. 

Here’s a guide to some of the top places to visit in this captivating region, complete with recommendations for activities, dining, and accommodation:

1. Decorah, Iowa

 

In the heart of the Driftless Region, Decorah, IA boasts stunning natural scenery, engaging cultural attractions, and some of the state’s best breweries, wineries, hiking, and biking trails. 

Stay at the B&B on Broadway, located a few blocks from the Trout Run Trail in Decorah’s historic district. This well-restored 1910 home showcases the woodwork and craftsmanship of the past while providing luxurious accommodations of the present. It includes a full breakfast made with local and organic ingredients. 

The B&B is an easy two-block walk to shops, dining, and entertainment. Enjoy lunch at La Rana Bistro, where its seasonal menu of small or large plates features local produce and a Spanish flare. 

After lunch, take a stroll down Water Street. You’ll find interesting shops to explore, including Agora Arts, where you’ll find a variety of artworks by artists throughout the Driftless Area available for admiring and purchasing.  

Enjoy a hike along Twin Springs’s cold water streams before dinner at Twin Springs Supper Club, which features locally sourced steaks, chops, and seafood.

2. Galena, Illinois

Whether you’re hiking or paddling the Apple River Canyon, treat yourself to a relaxing stay at Aldrich Guest House. This quaint inn with five guest rooms added a quirky “Potting Shed,” inviting you to enjoy nature’s cannabis. Yes, you read that right. 

Galena always has something around the corner to make you smile like the Galena Spoon Company. It’s an artist-operated shop with hand-carved spoons (of course!) and many handmade items for your culinary creations. They also offer in-store carving demonstrations daily. Durty Gurts for lunch is also a hoot with burgers, mixed drinks, and specialty shakes. After lunch, you might want to return to the Apple River Canyon or bike along the Galena River Trail. End your evening at the Goldmoor Inn for a memorable dinner.

3. Viroqua, Wisconsin

Tucked away in the rolling hills of southwestern Wisconsin, Viroqua is a haven for artists, foodies, and outdoor enthusiasts. Explore the evocative arts scene at the Driftless Folk School or browse the eclectic shops along Main Street. While you’re at it, it’s worth getting lost in Driftless Books & Music. 

There are also many opportunities for hiking, fishing, and canoeing in the surrounding countryside alongside the Kickapoo River. For dinner, try a locally sourced, farm-to-table meal at the Driftless Cafe.

Retreat to the historic charm of Hotel Fortney, a restored hotel featuring elegantly appointed rooms with unique charm and craftsmanship. 

4. Winona, Minnesota

Situated along the scenic banks of the Mississippi River, Winona, MN is a vibrant river town known for its stunning natural beauty and thriving arts community. Explore the Minnesota Marine Art Museum, stroll through the beautifully landscaped gardens at the Watkins Manor House, take a scenic drive along the Great River Road, or explore the unique shopping this picturesque town has to offer. 

There is also an 11-mile paddling trail outside of Winona, MN that traverses broad pools, islands, braided channels, and extensive bottomland forest. Wildlife enthusiasts can also visit the National Wildlife and Fish Refuge.

For dinner, indulge in upscale dining at Sullican’s Supper Club in nearby Trempeleau or at Signatures Restaurant located in town.

Wondering where to stay? The Carriage House Bed & Breakfast offers Victorian charm, artisanal breakfast, and warm hospitality. 

5. La Crosse, Wisconsin

Also perched on the banks of the Mississippi River, La Crosse, WI, is a lively city brimming with historic charm, outdoor recreation, and cultural attractions. Take a leisurely cruise along the Mississippi River, explore the historic downtown district, or hike to the top of Grandad Bluff for panoramic views of the city and surrounding countryside.

Indulge in farm-to-table cuisine at The Waterfront Restaurant and Tavern or savor classic American fare with a modern twist at The Charmant Hotel’s restaurant.

Experience luxury and sophistication at The Charmant Hotel, a beautifully restored candy factory turned boutique hotel offering stylish accommodations and exceptional dining options.

6. Dubuque, IA

Situated along the bluffs of the Mississippi River, Dubuque, IA, is a historic city with a rich heritage, eclectic cultural scene, and stunning riverfront views.

Explore the historic district’s cobblestone streets and 19th-century architecture, take a ride on the world’s shortest and steepest railroad, also known as the Fourth Street Elevator, or visit the National Mississippi River Museum & Aquarium.

For dining, enjoy contemporary American cuisine with a focus on locally sourced ingredients at Brazen Open Kitchen + Bar or dine in a restored historic mansion at Caroline’s Restaurant at the historic Hotel Julian.

Experience the charm of Victorian-era elegance at The Hancock House, a boutique bed and breakfast featuring beautifully appointed rooms and warm hospitality.

Start Your Driftless Journey

Whether you’re drawn to the historic charm of Galena, the natural beauty of Decorah, or the cultural attractions of La Crosse, the Driftless Area offers something for every traveler. So, pack your bags and embark on an unforgettable journey through this enchanting region.

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