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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

  • Trip Point Pin1

    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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  • Trip Point Pin2

    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.
    Open Google Maps Button
  • Trip Point Pin3

    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.
    Open Google Maps Button
  • Trip Point Pin4

    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.
    Open Google Maps Button
  • Trip Point Pin5

    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.
    Open Google Maps Button

Restaurants

  • Restaurant Icon

    Driftless Café

    4.7
    $$$$

    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.
    4.7
    $$$$
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    Rooted Spoon Kitchen Table

    4.7
    $$$$

    Rooted Spoon Kitchen Table

    An intimate dining experience in Viroqua, WI, known for its emphasis on seasonal, local produce served in a communal setting.
    4.7
    $$$$
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    Red Pines Bar & Grill

    4.7
    $$$$

    Red Pines Bar & Grill

    Located on the shores of Lake Onalaska, near La Crosse, WI, it offers delicious comfort food with stunning lake views.
    4.7
    $$$$
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    Rubaiyat Restaurant

    4.8
    $$$$

    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.
    4.8
    $$$$
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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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Hotels

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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

  • Event Icon

    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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    Turn Up the Good Times Tour featuring Warrant and Firehouse

    Turn Up the Good Times Tour featuring Warrant and Firehouse

    Turn Up the Good Times Tour featuring Warrant and Firehouse. Also appearing special guests Steelheart and Red Voodoo.
    Map IconLa Crosse Center in La Crosse (32.1 mi)
    Calendar Icon21 Mar 2026
    Picture for Turn Up the Good Times Tour featuring Warrant and Firehouse
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    Menopause The Musical 2

    Menopause The Musical 2

    The event will take place at Viterbo University Fine Arts Center in Onalaska.
    Map IconViterbo University Fine Arts Center in Onalaska (37.97 mi)
    Calendar Icon28 Oct 2025
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    Not Quite Brothers

    Not Quite Brothers

    N
    Map IconQ Casino Q Showroom in Dubuque (62.56 mi)
    Calendar Icon18 Oct 2025
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    Tracy Byrd

    Tracy Byrd

    Tracy Byrd became a household name on the Country Music Scene in 1993 when his third single, called "Holdin' Heaven", off of his MCA Records, self-titled debut album, hit #1 on the Billboard Country Charts. The Album also included the remake hit of J...
    Map IconQ Casino Q Showroom in Dubuque (62.56 mi)
    Calendar Icon26 Oct 2025
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  • Event Icon

    That Arena Rock Show

    That Arena Rock Show

    That Arena Rock Show is the ultimate high energy theatrical tribute to "Classic" Rock N' Roll. Performing legendary rock anthems that ruled the airwaves in the 70s and 80s. Including artists like: Led Zeppelin, Aerosmith, AC/DC, Bon Jovi, Guns N Rose...
    Map IconQ Casino Q Showroom in Dubuque (62.56 mi)
    Calendar Icon15 Nov 2025
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    The Pork Tornadoes

    The Pork Tornadoes

    The Pork Tornadoes are one of the most in-demand and popular party bands in the country. Having played over 800 shows for more than 1.5 Million people, they are known for putting a unique spin on all of your favorite songs, spanning 5 decades and 4 d...
    Map IconQ Casino Q Showroom in Dubuque (62.56 mi)
    Calendar Icon30 Nov 2025
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Travel Gems from Reddit

  • Reddit Icon

    On Saturday I took a little drive through the driftless zone in SW Wisconsin. So many curvy roads, beautiful valleys, and stunning scenery abounds. Lots of fun, quirky places,...

    Recommendations for a Driftless vacation

    On Saturday I took a little drive through the driftless zone in SW Wisconsin. So many curvy roads, beautiful valleys, and stunning scenery abounds. Lots of fun, quirky places,...

    /r/wisconsin
  • Reddit Icon

    Any recommendations for destinations in the driftless area? Looking to rent an AirBnb in small-ish towns that still have a downtown corridor

    Driftless Destinations?

    Any recommendations for destinations in the driftless area? Looking to rent an AirBnb in small-ish towns that still have a downtown corridor

    /r/wisconsin
  • Reddit Icon

    My wife and I are planning on taking a 4-5 day trip to the driftless region in spring. This will be our first trip there, and we want to bring our two smaller (20lbs) dogs wit...

    Driftless Region, recommendations of where to stay

    My wife and I are planning on taking a 4-5 day trip to the driftless region in spring. This will be our first trip there, and we want to bring our two smaller (20lbs) dogs wit...

    /r/wisconsin
  • Reddit Icon

    Posted by u/[Deleted Account] - 7 votes and 15 comments

    Scenic places to visit in The Driftless area?

    Posted by u/[Deleted Account] - 7 votes and 15 comments

    /r/wisconsin
  • Reddit Icon

    52 votes, 50 comments. Hi All, taking a trip down to the Driftless area in WI soon. We'll be near the Viroqua/LaCrosse area and are interested in

    Driftless WI Food Recommendations

    52 votes, 50 comments. Hi All, taking a trip down to the Driftless area in WI soon. We'll be near the Viroqua/LaCrosse area and are interested in

    /r/wisconsin

Music for Your Journey

  • Music Icon

    John Denver - Take Me Home, Country Roads

    John Denver - Take Me Home, Country Roads

    A classic road trip anthem that captures the spirit of adventure and tranquility.
    Listen on Spotify
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    Willie Nelson - On The Road Again - Live

    Willie Nelson - On The Road Again - Live

    A perfect companion for any journey, celebrating the joy of travel and exploration.
    Listen on Spotify
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    Rascal Flatts - Life is a Highway

    Rascal Flatts - Life is a Highway

    An energetic tune to keep the spirits high as you cruise through the country roads.
    Listen on Spotify
    Picture for Rascal Flatts - Life is a Highway
  • Music Icon

    The Chicks - Wide Open Spaces

    The Chicks - Wide Open Spaces

    Captures the longing for freedom and the excitement of discovering new places.
    Listen on Spotify
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  • Music Icon

    Edward Sharpe & The Magnetic Zeros - Home

    Edward Sharpe & The Magnetic Zeros - Home

    A comforting song about belonging and the feeling of being at home, wherever you are.
    Listen on Spotify
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    The Head And The Heart - Rivers and Roads

    The Head And The Heart - Rivers and Roads

    A reflective song about the passage of time and the journey, both physically and emotionally.
    Listen on Spotify
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  • Music Icon

    Allman Brothers Band - Ramblin' Man

    Allman Brothers Band - Ramblin' Man

    An ode to the traveler in search of new experiences and adventures.
    Listen on Spotify
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    Tracy Chapman - Fast Car

    Tracy Chapman - Fast Car

    A narrative of aspirations and the freedom found on the open road.
    Listen on Spotify
    Picture for Tracy Chapman - Fast Car
  • Music Icon

    Talking Heads - Road to Nowhere

    Talking Heads - Road to Nowhere

    A quirky and upbeat song about the joys and unpredictability of travel.
    Listen on Spotify
    Picture for Talking Heads - Road to Nowhere
  • Music Icon

    Don McLean - American Pie

    Don McLean - American Pie

    An evocative journey through the vast landscapes and diverse cultures of America.
    Listen on Spotify
    Picture for Don McLean - American Pie