5 Essential Midwest Road Trips

Great River Road

MINNESOTA, WISCONSIN, IOWA, AND MISSOURI

To appreciate America’s most magnificent river, take a trip down the Mississippi along the Great River Road National Scenic Byway — the oldest scenic byway in the country. Along the Great River Road, you’ll find exciting things to explore including river-related attractions, tiny riverside villages, and vibrant cities. It’s like experiencing the living history of the region through music, culture, and local cuisine. Starting in Brainerd, Minnesota, head south to hike the trails and see the house where Charles Lindbergh grew up at Charles Lindbergh State Park. Then, travel to the quaint town of Potosi, Wisconsin, and visit the National Brewery Museum, before heading to Le Claire, Iowa — the perfect place to take a ride on an iconic Mississippi River riverboat and stop at Antique Archaeology, the shop featured on the TV show “American Pickers.” No trip down the Mississippi would be complete without a visit to Hannibal, the hometown of one of the most beloved American authors, Mark Twain. Twain’s boyhood home and museum features 15 original Norman Rockwell oil paintings.

The Badlands

SOUTH DAKOTA

A road trip through South Dakota will awaken the nature lover in you. There is so much natural beauty on this drive that you’ll barely have to leave the road to find it. Start your trip on the 40-mile-long Badlands Loop Scenic Byway (SD 240). The scenic drive boasts the most stunning buttes, cliffs, and multi-colored spires found in Badlands National Park. Heading west on SD 240, you’ll run right into one of America’s most iconic sights — Gutzon Borglum’s wondrous mountain sculpture Mount Rushmore. The massive carved faces of Presidents Washington, Jefferson, Roosevelt, and Lincoln will simply leave you with a sense of awe. Your last stop through the Badlands of South Dakota should be Custer State Park. Here you’ll see herds of bison wandering the rolling plains. It’s a great place to stop and experience the wide-open ranges while enjoying wildlife.

Great Lakes Road Trip

MICHIGAN

This epic, 500-mile road trip bridges Michigan’s Upper and Lower Peninsulas. Begin your journey at Sleeping Bear Dunes National Lakeshore for terrific views of the Manitou Islands. The next stop is a three-hour ride up US 31 along the Grand Traverse Bay to Mackinaw City. There, you can visit the Headlands International Dark Sky Park for the best stargazing spot on Michigan’s Lower Peninsula. Head down to Lake Huron to catch the sunrise and cross the Mackinac Bridge — the third-longest suspension bridge in the world. The first stop in the Upper Peninsula is Pictured Rocks National Lakeshore, where you can rent a kayak and paddle to the caves and cliffs. After your time at the shore, it’s off to Marquette — a quaint town with Finnish heritage. The last stop on this journey is Copper Harbor — the northernmost city in Michigan. A stop at the Thunderbird Gifts at Minnetonka Resort is also a must for silver and turquoise jewelry.

Best Big Cities

KENTUCKY TO WISCONSIN

If you’re looking to take a road trip that hits some of the biggest cities in the Midwest, this trip is for you. Starting in Louisville, Kentucky, baseball fans will love the Louisville Slugger Museum and the story behind the world-famous baseball bat. Head north on I-65, and you’ll end up in Indianapolis. Indy is known for the fast cars that circle Motor Speedway every year, but the city has also gained acclaim for a flourishing culinary and brewing scene. Back on I-65 North, head off to the Windy City. Chicago is one of the most visited cities in the Midwest for good reason with attractions like the Skydeck at Willis Tower, the Lincoln Park Zoo, the Garfield Park Conservatory, and the Shedd Aquarium. The last leg of this essential Midwest road trip is the drive from Chicago to Milwaukee, Wisconsin along Lake Michigan. Milwaukee is the “beer capital of the world” and home to one of the biggest names in hops and barley — Miller. It’s the brewpubs that bring people to Milwaukee today. After a tour of the Lakefront Brewery, you’ll see why.

Music Lovers Road Trip

MISSOURI TO KANSAS

If you’re a fan of blues and jazz music, then this road trip from St. Louis, Missouri to Kansas City, Kansas will be hardwired into your DNA. Your trip starts in St. Louis, which is home to the iconic 1914 song “St. Louis Blues.” You can learn more about the history of this song and other blues music tunes at the National Blues Museum. When you finally leave the “Gateway to the West,” travel through the Ozark Mountains on parts of historic Route 66 — the famous byway that runs on scenic roads across the American West from Chicago to Santa Monica, California. Stop off Route 66 to stroll around Branson, Missouri. The area around Branson is filled with scenic lakes and forests, but the emergence of Branson as the “live music show capital of the world” draws visitors from around the globe. The last leg of this musical road trip takes you north to Kansas City. Kansas City is where notable jazz musicians like Charlie Parker and Count Basie got their start in the 1920s and 1930s by playing clubs in the historic 18th and Vine district. Today, you can relive those glory days at the American Jazz Museum.