Embark on a road trip that promises not just miles but memories, from the charming waterfronts of Kenosha, Wisconsin, to the bustling urban landscapes of Minneapolis, Minnesota. This meticulously planned itinerary ensures that every stop is a pause in your journey and a highlight in your adventure.

Day 1: Departure from Kenosha

Morning: Kenosha’s Lakeside Charms

Kick off your adventure in Kenosha right by the water’s edge. Begin with a sunrise stroll along Kenosha’s scenic HarborPark, where the early light glistens over Lake Michigan. This area, beautified with art installations and well-kept pathways, is perfect for capturing the serene morning hours.

After your walk, explore local history at the Kenosha Public Museum. The mammoth exhibit, which showcases a fascinating collection of local Ice Age fossils, is an absolute must-see. The museum also offers an array of exhibits, from fine arts to cultural artifacts, that tell the story of the region’s development.

Late Morning: Breakfast and More

Refuel with a hearty breakfast at one of Kenosha’s charming lakeside cafés. The Coffee Pot is a local favorite, known for its generous servings of home-style breakfasts and a cozy retro vibe. Try their famous corned beef hash or indulge in a stack of pancakes before heading out.

Midday: A Quick Stop in Racine

En route to Milwaukee, make a brief detour to Racine. Visit the Wind Point Lighthouse, one of the oldest and tallest active lighthouses on the Great Lakes. The grounds offer a picturesque setting for a leisurely walk and some great photo opportunities.

Afternoon: Exploring Milwaukee

Arrive in Milwaukee by early afternoon, just in time to explore its rich cultural tapestry. Start with the Milwaukee Art Museum, known not only for its impressive collection of over 25,000 works of art but also for its stunning architectural design. The building itself, with its dynamic brise-soleil (a moveable sunscreen resembling wings), is a piece of art.

For lunch, head to the Historic Third Ward, where the Milwaukee Public Market presents a variety of local foods and goods. Sample Wisconsin cheeses at West Allis Cheese & Sausage Shoppe, or grab an authentic Mexican meal at Margarita Paradise.

Late Afternoon: Discover Milwaukee’s Old World Third Street

Before leaving Milwaukee, stroll down Old World Third Street, an area steeped in German heritage. Visit the renowned Usinger’s Famous Sausage, a historic spot offering a wide array of German sausages that have been made using traditional recipes for over a century.

Evening: Arrival in La Crosse

Conclude your first day in La Crosse, a city that epitomizes the beauty of the Upper Midwest with its riverside parks and vibrant downtown. Check into your hotel and unwind. Consider The Waterfront Restaurant and Tavern for upscale dining with impressive river views for dinner. Savor dishes like the pan-seared walleye or the grilled ribeye, and toast to the first day of your memorable road trip.

Night: Sunset at Grandad Bluff

If you’re up for one more outing, drive up to Grandad Bluff for a breathtaking view of La Crosse and the surrounding area, especially beautiful at sunset. The bluff, the highest point in the area, offers panoramic views of the Mississippi River and beyond, a perfect backdrop for reflecting on the day’s journey and looking forward to the adventures yet to come.

Day 2: Wabasha to Minneapolis

Morning: Departure from La Crosse

Wake up refreshed in La Crosse and start your day with breakfast at Fayze’s, a beloved local bakery and restaurant. Enjoy their homemade pastries and an omelet made with fresh, local ingredients. Before leaving La Crosse, take a moment to walk through Riverside Park, where the early morning serenity of the Mississippi River provides a peaceful start to your day.

Mid-Morning: Scenic Drive to Wabasha

The journey from La Crosse to Wabasha is as scenic as it is serene. It takes you along the Great River Road, which offers stunning views of the Mississippi River and the surrounding bluffs. This route is known for its beautiful vistas and is often considered one of the best river drives in the United States.

Late Morning: National Eagle Center in Wabasha

Arrive in Wabasha, a charming river town home to the National Eagle Center. Here, you can attend live eagle programs to meet resident bald and golden eagles face-to-face. Learn about these magnificent birds’ biology, ecology, and natural history. The center’s large windows and outdoor observation deck also offer a perfect spot for wild eagle viewing, especially during migration periods.

Lunch in Wabasha

For lunch, stop by the Olde Triangle Pub, a cozy spot with hearty meals and a welcoming atmosphere. Enjoy some Irish-American classics and local delicacies, and perhaps chat with locals about the town’s history and their river way of life.

Early Afternoon: Historic Red Wing

Next, head to Red Wing, about a 45-minute drive from Wabasha. Red Wing is famous for its antique shops, pottery, and the Red Wing Shoes store and museum. Spend some time exploring the historic downtown. Visit the Red Wing Pottery Museum to see a vast collection of vintage stoneware, art pottery, and folk art.

Mid-Afternoon: Drive to Minneapolis

Continue your road trip by heading towards Minneapolis. This part of the drive winds through some picturesque areas along the Mississippi, offering opportunities to stop at roadside viewpoints.

Late Afternoon: Arrival in Minneapolis

Upon arrival in Minneapolis, check into your hotel and take a short rest. Then, prepare for an evening of exploring the city. Start with a visit to the Minneapolis Institute of Art, which boasts a vast and varied collection from ancient sculptures to contemporary photography.

Dinner in Minneapolis

For dinner, head to the North Loop, where you can find a range of dining options. Spoon and Stable, a restaurant set in a converted horse stable, offers a fantastic dining experience with a menu that reflects the Midwest’s seasonal produce.

Evening: Explore Uptown Minneapolis

After dinner, explore Uptown, a vibrant neighborhood known for its lively nightlife and cultural scene. You can catch a film at the historic Uptown Theatre or enjoy a drink at one of the local rooftop bars, offering great views of the city skyline.

Night: Minneapolis by Night

Conclude your evening with a leisurely stroll around one of Minneapolis’s scenic lakes, like Lake of the Isles, perfect for a night walk under the stars.

Highlights of Your Road Trip

• Kenosha’s Lakefront Beginnings: Start your trip with serene views and local history.
• Milwaukee’s Art and Culinary Delights: Experience the city’s rich arts scene and culinary excellence.
• Madison’s Cultural Pulse: Discover the vibrant life of Wisconsin’s capital.
• La Crosse’s Riverfront Relaxation: Enjoy the beauty and tranquility of the Mississippi River.
• Wabasha’s Eagles: Get up close with majestic eagles and learn about local wildlife.
• Minneapolis’s Artistic Finale: Dive into the cultural richness of one of the Midwest’s major cities.

Travel Tips

• Best Travel Time: Late spring through early fall offers the best weather for road-tripping in this region.
• Packing Essentials: Bring layers, as temperatures can vary, especially if you’re near the lakes at night.
• Road Conditions: Keep an eye on local travel advisories, especially during winter.

This Kenosha to Minneapolis road trip itinerary offers a blend of natural beauty, cultural experiences, and urban exploration. It’s not just about the destinations but the journey between that will enrich your travel experience, making each mile a memory to cherish. Whether you’re a solo adventurer, a couple, or a family, this road trip caters to all eager to explore America’s heart.