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06 May 2025
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Driftless Region Road Trip Itinerary

Driftless Discovery Road Trip Overview

Embark on an unforgettable road trip through the scenic Driftless Region, a unique landscape untouched by glaciers with rolling hills, deep river valleys, and charming small towns. Your journey begins in Viroqua, Wisconsin, a quaint locale that captures the essence of the Driftless Area. Here, you'll find a vibrant arts scene and local farmers' markets that offer a delightful taste of sustainable living and community spirit.

Next, venture into the natural beauty of Wildcat Mountain State Park. This stunning park offers breathtaking views of the Kickapoo Valley with trails perfect for hiking and horseback riding, as well as canoeing opportunities on the Kickapoo River, a perfect retreat for outdoor enthusiasts seeking serenity and adventure.

Continue your exploration in La Crosse, WI, a city that sits proudly along the Mississippi River. Known for its historic downtown and lively cultural scene, La Crosse offers bluff-top parks with panoramic views and a calendar full of festivals and theater productions. It's an ideal spot for those looking to dive into regional history and vibrant local culture.

Your journey then takes you to Decorah, Iowa, a town steeped in Norwegian heritage. Decorah impresses visitors with its beautiful parks, renowned Decorah Eagles, and a thriving arts and music scene. Finish your adventure in Dubuque, Iowa, where majestic riverfront views complement historic architecture. Visit attractions such as the National Mississippi River Museum & Aquarium for a dose of regional history and cutting-edge exhibits that broaden your understanding of America's waterways.

Throughout this road trip, discover the Driftless Region's charm, history, and natural beauty, offering an enriching escape into the heartland's unique landscape and vibrant communities.


Recommended Activities

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    Viroqua, WI

    Viroqua is known for its charming small-town atmosphere, vibrant arts scene, and local farmers' markets, offering a taste of local culture and sustainable living.
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    Wildcat Mountain State Park, WI

    Wildcat Mountain State Park offers breathtaking views of the Kickapoo Valley, along with opportunities for hiking, horseback riding, and canoeing, making it a perfect spot for nature lovers and outdoor enthusiasts.
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    La Crosse, WI

    La Crosse, situated along the Mississippi River, is known for its historic downtown, bluff-top parks offering panoramic river views, and its lively cultural scene, including festivals and theater productions.
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    Decorah, IA

    Decorah is renowned for its rich Norwegian heritage, beautiful parks, and the famed Decorah Eagles. The town also offers a vibrant arts and music scene, along with unique shops and eateries.
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    Dubuque, IA

    Dubuque is known for its stunning riverfront views, historic architecture, and attractions such as the National Mississippi River Museum & Aquarium, making it a cultural and educational hub in the area.
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Tasty Picks

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    Driftless Café

    4.3
    $$$$

    Driftless Café

    Located in Viroqua, WI, this farm-to-table restaurant is celebrated for its creative use of local, organic ingredients, providing a true taste of the Driftless Region's bounty.
    4.3
    $$$$
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    Rooted Spoon Kitchen Table

    Rooted Spoon Kitchen Table

    An intimate dining experience in Viroqua, WI, known for its emphasis on seasonal, local produce served in a communal setting.
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    Red Pines Bar & Grill

    4.2
    $$$$

    Red Pines Bar & Grill

    Located on the shores of Lake Onalaska, near La Crosse, WI, it offers delicious comfort food with stunning lake views.
    4.2
    $$$$
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    Rubaiyat Restaurant

    4.2
    $$$$

    Rubaiyat Restaurant

    Nestled in Decorah, IA, this restaurant offers a worldly menu with a focus on fresh, locally-sourced ingredients, pairing meals with an extensive wine list.
    4.2
    $$$$
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    L.May Eatery

    4.7
    $$$$

    L.May Eatery

    Situated in Dubuque, IA, this cozy restaurant serves gourmet American cuisine with a creative twist, emphasizing locally sourced ingredients.
    4.7
    $$$$
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Stay Recommendations

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    Viroqua Heritage Inn Bed & Breakfast

    4.6

    Viroqua Heritage Inn Bed & Breakfast

    Located in Viroqua, WI, this charming B&B offers a historic stay in beautifully restored Victorian-era homes amidst the heart of the Driftless Region.
    4.6
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    Justin Trails Resort

    4.8

    Justin Trails Resort

    A unique getaway near Sparta, WI, offering eco-friendly lodgings such as log cabins and a yurt amidst a picturesque countryside setting.
    4.8
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    Grist Mill Lodge

    Grist Mill Lodge

    Located in the scenic village of Burr Oak, IA, this rustic lodge provides a peaceful retreat with its beautifully restored interiors and lush surroundings.
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    Four Mounds Inn & Conference Center

    4.8

    Four Mounds Inn & Conference Center

    Situated in Dubuque, IA, this inn offers vintage-style accommodations within a historic estate, set amidst expansive grounds overlooking the Mississippi River.
    4.8
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    Hotel Julien Dubuque

    Hotel Julien Dubuque

    A luxury boutique hotel in Dubuque, IA, Hotel Julien offers a blend of historic charm and modern amenities, located in the vibrant downtown area.
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Local Events & Happenings

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    ADAM CALHOUN - THE WAR TOUR in La Crosse

    ADAM CALHOUN - THE WAR TOUR in La Crosse

    ADAM CALHOUN - THE WAR TOUR in La CrosseWith Special Guests: Hard Target, Cymple Man, Dusty Leigh6PM $35 All Ageswww.LeoPresents.com
    Map IconCavalier Theater in La Crosse (32 mi)
    Calendar Icon1 Nov 2025
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    The Avett Brothers

    The Avett Brothers

    4 ticket limit per order
    Map IconLa Crosse Center in La Crosse (32.1 mi)
    Calendar Icon29 Aug 2025
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    Elvis Explosion

    Elvis Explosion

    Elvis Explosion Package Tickets are On Sale May 15 at 11 AM until June 15. Individual Event Tickets are On Sale June 16 at 11 AM.
    Map IconLa Crosse Center in La Crosse (32.1 mi)
    Calendar Icon6 Sep 2025
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    Elvis Explosion Package

    Elvis Explosion Package

    Elvis Explosion Package Tickets are On Sale May 15 at 11 AM until June 15. Individual Event Tickets are On Sale June 16 at 11 AM.
    Map IconLa Crosse Center in La Crosse (32.1 mi)
    Calendar Icon6 Sep 2025
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    Tim McGraw

    Tim McGraw

    The event will take place at Field of Dreams Iowa in Dyersville.
    Map IconField of Dreams Iowa in Dyersville (61.05 mi)
    Calendar Icon31 Aug 2025
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    Brothers Osborne

    Brothers Osborne

    Two sons from a working-class family, John and TJ Osborne grew up in the small water town of Deale, Maryland, writing and playing songs for friends and family in their father?s shed. John moved to Nashville first to play in other bands and two years ...
    Map IconQ Casino Back Waters Stage in Dubuque (62.54 mi)
    Calendar Icon23 Aug 2025
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    Bush

    Bush

    In 1994, Bush found immediate success outside the UK with the release of their debut album, Sixteen Stone, which is certified six times multi-platinum by the RIAA.[2] They went on to become one of the most commercially successful rock bands of the 19...
    Map IconQ Casino Back Waters Stage in Dubuque (62.54 mi)
    Calendar Icon7 Sep 2025
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Travel Gems from Reddit


Music for Your Journey