The Beauty of the Driftless Region
Unlike much of the Midwest, the Driftless Region was untouched by glaciers during the last Ice Age, leaving behind a unique landscape of dramatic bluffs, steep valleys, and winding waterways. Scenic byways such as the Minnesota Great River Road - Highway 61 along the Mississippi River and lesser-traveled backroads reveal breathtaking vistas at every turn, with vibrant foliage in the fall and lush greenery in the warmer months.
This section of the Mississippi River is part of the Upper Mississippi River National Wildlife and Fish Refuge, a critical habitat for migrating waterfowl, bald eagles, and other bird species. Birdwatchers flock to the area in spring and fall for the remarkable displays of wildlife, making it a destination for nature lovers year-round.
Charming Towns with Unique Appeal
Just a short drive from Winona, you’ll find several small towns that each have their own character and attractions. Head south to Pickwick, which boasts the historic Pickwick Mill, a must-see landmark showcasing Minnesota’s milling history and picturesque surroundings perfect for photography. And when heading that direction don’t miss the stunning scenic vistas at Great River Bluffs State Park, just 20 miles south of Winona.
To the west, St. Charles, often called the “Gateway to Whitewater,” is a charming hub for those heading to Whitewater State Park. This park is a paradise for hikers and birdwatchers, offering trout streams, limestone bluffs, and year-round wildlife viewing.
Across the river in Wisconsin, small towns like Fountain City, Alma, Trempealeau, Arcadia, and Centerville offer even more to explore. Fountain City is known for its quirky treasures like the Rock in the House and its inviting riverfront vibe. Alma’s historic downtown, set on a steep bluff, offers breathtaking views and unique shops.
Trempealeau is a true gem for outdoor enthusiasts. Situated along the river and home to Perrot State Park, this town offers fantastic hiking trails, charming local eateries, and a laid-back atmosphere. The Trempealeau Hotel is a must-visit, known for its live music and fantastic views of the Mississippi.
Inland from the river, Arcadia and Centerville highlight Wisconsin’s agricultural charm. Arcadia boasts the expansive Memorial Park, home to unique sculptures and events, and it is home to the annual Ashley for the Arts concert. Centerville offers a quieter, pastoral setting with home-style eateries and a large curling club. The scenic river road leading there is dotted with apple orchards and quaint shops selling produce, honey, flowers, and more.
Just 30 miles south of Winona, the La Crosse-Onalaska area in Wisconsin offers additional shopping, dining, and cultural activities to round out your visit. With its larger population, it complements the smaller communities of the Driftless Region while maintaining the same focus on natural beauty and riverfront charm.
These towns, with their unique blend of history, charm, and access to outdoor adventure, make the Driftless Region an endlessly fascinating area to explore.
Top Attractions for Sightseeing
The surrounding area is rich with sightseeing opportunities for visitors of all interests. The Great River Road National Scenic Byway runs through the region, offering iconic views of the Mississippi River valley and leading to charming river towns like Wabasha, which is home to the National Eagle Center. There, visitors can learn about and observe these majestic birds in their natural habitat.
The drive north along the Wisconsin side of the river offers stunning bluff views plus a few great discoveries, such as the Prairie Moon Sculpture Garden, a strange homage to a man’s creative eye, and Kinstone, an incredible 30-acre megalithic stone sculpture garden that features special events such as drum circles and full-moon gatherings, plus educational events and retreats.
Heading south on the Wisconsin side, orchards and roadside stands offer fresh produce plus delicious tastes of the Driftless Region apples. Don’t miss the Berry Market, Schwertel Family Farm or Eckers Apple Farm for an afternoon enjoying shopping plus tasting delicious regional ciders and beers in fun family settings.
Outdoor enthusiasts will love exploring the Root River Trail system, which connects several towns with paved paths ideal for biking, hiking, and cross-country skiing. For a quieter experience, consider paddling or fishing on one of the area’s hidden gem streams like Trout Run Creek or Beaver Creek.
Winona's Wine Country
For those who enjoy a bit of local flavor, the area’s wineries offer the perfect way to relax while sampling the region’s bounty. The area contains a number of wineries, many of which belong to a unique group called the Great River Road Wine Trail, including Garvin Heights Vineyards, Elmaro Vineyard, Bluff Top Vineyard, River View Vineyard, and Seven Hawks Vineyards.
State Parks Galore
Nature lovers will find plenty to explore in the state parks dotting both sides of the Mississippi. In Minnesota, Whitewater and Great River Bluffs State Parks provide incredible hiking trails, panoramic views, and opportunities for wildlife spotting. On the Wisconsin side, Merrick State Park and Perrot State Park offer tranquil riverside settings for camping, canoeing, and birdwatching, with Perrot’s Brady’s Bluff offering some of the most stunning vistas in the region. These parks highlight the natural beauty of the Driftless Region and make the area a top destination for outdoor recreation.