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16 Mar 2025Updated last time
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Wisconsin To Texas Road Trip Trip Itinerary

Trip Itinerary Overview: Wisconsin to Texas Road Adventure

Embark on an exciting road trip from the Great Lakes of Wisconsin to the vibrant landscapes of Texas, uncovering culturally rich cities and natural wonders along the way. Start your journey in Milwaukee, Wisconsin, known for its brewing heritage and stunning lakefront views. As you travel south, make a stop in Chicago, Illinois, a bustling metropolis famed for its architectural marvels, deep-dish pizza, and cultural landmarks like the Art Institute of Chicago.

Your travels then take you to St. Louis, Missouri, where the iconic Gateway Arch stands as a testament to America's westward expansion. Experience the city's rich musical legacy and enjoy its delightful barbecue cuisine. Continue your journey to Springfield, Missouri, the gateway to the scenic Ozarks, offering outdoor adventures and attractions such as Fantastic Caverns.

As you venture further, Oklahoma City, Oklahoma awaits, presenting a rich tapestry of cowboy culture and history, alongside a vibrant arts scene. Delve into its Western heritage at the National Cowboy & Western Heritage Museum. Upon reaching Dallas, Texas, embrace the city's modern flair, shopping opportunities, and cultural experiences, including a visit to the Sixth Floor Museum at Dealey Plaza.

Your road trip culminates in the lively city of Austin, Texas. Known as the "Live Music Capital of the World," Austin offers an eclectic mix of live performances, diverse culinary delights, and beautiful outdoor spaces like Barton Springs and Lady Bird Lake. This trip promises a fusion of history, culture, and natural beauty, creating unforgettable memories.


Recommended Activities

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    Milwaukee, Wisconsin

    Milwaukee is known for its brewing traditions, vibrant arts scene, and beautiful lakefront. The Milwaukee Art Museum and the Historic Third Ward offer unique cultural experiences.
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    Chicago, Illinois

    Chicago is a bustling metropolis with iconic architecture, world-class museums, and diverse neighborhoods. Highlights include Millennium Park, the Art Institute of Chicago, and deep-dish pizza.
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    St. Louis, Missouri

    St. Louis is famous for its Gateway Arch, a symbol of westward expansion, as well as its rich musical history, including blues and jazz, and delicious barbecue cuisine.
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    Springfield, Missouri

    Springfield offers a mix of outdoor adventures and cultural experiences. It's the gateway to the Ozarks and home to attractions like Fantastic Caverns and the Wonders of Wildlife National Museum & Aquarium.
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    Oklahoma City, Oklahoma

    Oklahoma City boasts a rich cowboy culture and history with attractions like the National Cowboy & Western Heritage Museum, as well as a vibrant arts scene and entertainment district.
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    Dallas, Texas

    Dallas is known for its modern skyline, shopping, and cultural institutions such as the Dallas Museum of Art and the Sixth Floor Museum at Dealey Plaza, which chronicles the life of JFK.
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    Austin, Texas

    Austin is renowned for its vibrant live music scene, diverse food culture, and outdoor spaces. Known as the 'Live Music Capital of the World', it offers numerous festivals, eclectic neighborhoods, and the scenic beauty of Barton Springs and Lady Bird Lake.
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Restaurants

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    SafeHouse - Milwaukee, Wisconsin

    SafeHouse - Milwaukee, Wisconsin

    A spy-themed restaurant in Milwaukee offering a fun, secretive dining experience with hidden entrances and spy gadgets.
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    The Berghoff

    The Berghoff

    An iconic German restaurant in Chicago, serving traditional fare in a historic setting with unique 19th-century charm.
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    Crown Candy Kitchen

    4.5
    $$$$

    Crown Candy Kitchen

    A nostalgic St. Louis spot known for its hearty sandwiches, sweet treats, and historic soda fountain ambiance.
    4.5
    $$$$
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    Pappy's Smokehouse

    Pappy's Smokehouse

    This Springfield favorite is renowned for its Memphis-style BBQ, offering mouthwatering ribs and smoked meats.
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    Truck Yard

    4.3

    Truck Yard

    An Austin hotspot offering a vibrant outdoor scene with food trucks, live music, and an eclectic selection of drinks.
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Hotels

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    The Iron Horse Hotel - Milwaukee, Wisconsin

    The Iron Horse Hotel - Milwaukee, Wisconsin

    A chic, bike-friendly hotel in Milwaukee housed in a converted 100-year-old warehouse, offering a unique industrial vibe.
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    Chicago Athletic Association Hotel - Chicago, Illinois

    4.6

    Chicago Athletic Association Hotel - Chicago, Illinois

    A historic, luxury hotel occupying a Venetian Gothic-style building in Chicago, offering game rooms and period architectural details.
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    The Cheshire Hotel, St. Louis

    4.1

    The Cheshire Hotel, St. Louis

    A charming British-inspired hotel in St. Louis showcasing English countryside decor and literary-themed suites.
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    21c Museum Hotel Oklahoma City

    21c Museum Hotel Oklahoma City

    A unique hotel and contemporary art museum in a restored Ford Motor Company assembly plant, featuring rotating art exhibitions.
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    The Belmont Hotel

    The Belmont Hotel

    A retro-chic boutique hotel in Dallas offering stunning views of the city skyline and a vintage 1940s atmosphere.
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Local Events & Happenings

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    Springfield, MO - Sunday

    Springfield, MO - Sunday

    The event will take place at Great Southern Bank Arena in Springfield.
    Map IconGreat Southern Bank Arena in Springfield (6.98 mi)
    Calendar Icon31 Aug 2025
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    Dylan Scott

    Dylan Scott

    Doors 7:00pm / Show 8:00pm Reserved front arena seating (Sections A, B, J, H), General Admission floor and rear arena seating (sections C-G).
    Map IconShrine Mosque in Springfield (7.53 mi)
    Calendar Icon24 Oct 2025
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    Trivium: Ascend Above The Ashes Tour

    Trivium: Ascend Above The Ashes Tour

    Doors 6:30pm / Show 7:30pm Reserved front arena seating (Sections A, B, J, H), General Admission floor and rear arena seating (sections C-G).
    Map IconShrine Mosque in Springfield (7.53 mi)
    Calendar Icon10 Dec 2025
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    Josh Johnson

    Josh Johnson

    The event will take place at Gillioz Theatre in Springfield.
    Map IconGillioz Theatre in Springfield (7.53 mi)
    Calendar Icon14 Dec 2025
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    Josh Johnson: The Flowers Tour

    Josh Johnson: The Flowers Tour

    The event will take place at Gillioz Theatre in Springfield.
    Map IconGillioz Theatre in Springfield (7.59 mi)
    Calendar Icon14 Dec 2025
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Travel Gems from Reddit


Music for Your Journey

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    Willie Nelson - On The Road Again - Live

    Willie Nelson - On The Road Again - Live

    A classic road trip anthem that captures the excitement of travel.
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    Bruce Springsteen - Born to Run

    Bruce Springsteen - Born to Run

    An exhilarating rock song that embodies freedom and the open road.
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    Lynyrd Skynyrd - Sweet Home Alabama

    Lynyrd Skynyrd - Sweet Home Alabama

    A Southern rock classic that celebrates the spirit of the South.
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    Eagles - Take It Easy - 2013 Remaster

    Eagles - Take It Easy - 2013 Remaster

    A laid-back tune that perfectly complements a relaxed drive.
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    Rascal Flatts - Life is a Highway

    Rascal Flatts - Life is a Highway

    An energetic song about the joys and challenges of life's journey.
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    Chuck Berry - Route 66

    Chuck Berry - Route 66

    A jazzy track that pays homage to the iconic American highway.
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    M83 - Midnight City

    M83 - Midnight City

    An upbeat, synth-driven anthem perfect for night driving.
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    Eagles - Hotel California - 2013 Remaster

    Eagles - Hotel California - 2013 Remaster

    A mysterious and iconic rock ballad with a compelling story.
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    John Denver - Take Me Home, Country Roads

    John Denver - Take Me Home, Country Roads

    A nostalgic song celebrating the beauty of scenic countryside drives.
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    Led Zeppelin - Ramble On - 1990 Remaster

    Led Zeppelin - Ramble On - 1990 Remaster

    A classic rock tune that captures the essence of adventure and exploration.
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