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Planning a Midwest road trip? You’re sure to have a blast, as this area of the country offers an abundance of activities, vast landscapes and plenty of room for exploration. 

But if you need a bit of help putting together a road trip itinerary, we’ve rounded up 3 scenic drives in the Midwest you’re sure to love.

Best Road Trip Destinations in the Midwest 

For a Midwest road trip itinerary that’s sure to please the entire family, consider exploring this region with one of these scenic drives.

1. Explore Route 66: Chicago, IL to St. Louis, Missouri


Up for a little adventure? Start in the Windy City, where the historic sign stands for the beginning of Route 66.

  • Take a drive and enjoy the Midwest portion of the route, filled with iconic sights and activities.
  • After loading up on a deep dish meal in Chicago, head over to Wilmington, IL (60-miles away) to visit the Gemini Giant, a landmark stature on Route 66. The 30-foot-tall “Muffler Man,” sits right outside the Launching Pad drive-in restaurant and offers visitors an artistic glimpse of props found throughout the USA in the sixties, including a silver rocket ship, astronaut’s space helmet and more.
  • Next, head over to Springfield, IL where history enthusiasts can check out Abraham Lincoln’s home, tomb and the Presidential Library and Museum.
  • Finally, end your Mid-west adventure with an overnight stay in St. Louis, where iconic sights such as the Gateway Arch National Park, City Museum and the Chain of Rocks Bridge are sure to delight!

    2. Discover Minnesota Through a Scenic Drive Along Lake Superior

    Prefer to stick to one state on your road trip in the Midwest? Minnesota provides a range of activities sure to delight every type of traveler!
    • For the beer-enthusiast and craft cocktail aficionados, head over to Duluth, Minnesota where you’ll find an intriguing craft beer scene and an award winning micro-distillery, Vikre Distillery, located at the foot of the iconic Aerial Lift Bridge. While in the area, be sure to also check out Bob Dylan Way, for a glimpse of the music legend’s birthplace.
    • If you love photography and exploring the outdoors, head over to Gooseberry Falls and Split Rock Lighthouse (the most photographed spots within the state), near Two Harbors, Minnesota, to see stunning vistas and cascading waterfalls.
    • Shopping enthusiasts will love spending a day at the Mall of America, the nation’s biggest mall with over 500 stores.
    • Backpackers will want to explore Boundary Waters Canoe Area Wilderness in the northeastern tip of the state. With over 1 million acres to roam, this is a backpacker’s paradise. There are several hiking trails and over 1,200 miles of canoe routes, creating the perfect outdoor escape to disconnect

    3. Splurge on a Getaway to Greenough, MT

    Whether you’re looking to get away with your immediate family, or planning more of a multi-family excursion, The Resort at Paws Up, located in Greenough, MT, provides an expansive playground of over 37,000-acres, for the ultimate getaway. Go glamping in one of their signature multi-person tents or chose from one of their many timber cabins for luxurious accommodations. What should you do?

    • Go glamping in one of their signature multi-person tents or chose from one of their many timber cabins for luxurious accommodations.
    • The resort offers various activities including fly-fishing, horseback riding, ATVs, mountain biking, all-you-can eat buffets and more!

    A Word of Safety

    No matter which of these best Midwest road trips you decide to take, make sure you do your due diligence and check to see what’s open and what’s not due to COVID-19. The health and safety of you, your friends, and your family should always be a top priority. 

    To make your travels as convenient as possible, pack appropriately for the length of your trip and, of course, the amount of space you’ll have available in your vehicle. In need of new luggage or don’t have the right bag for your Midwest adventure? ShopBriggs and Riley to find exactly what you need. 


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