Your Northern Cross Country Road Trip Continues: A Groaning Buffet of Sights (Can You Handle It?)

Chicago, IL
Continue your cross country road trip in Chicago – the "Windy City". You’ll be close by on the shores of Lake Michigan, so it’s the most appropriate next “hit” on your hit list. Chicago is a great city – one of the best in the U.S. – and there is a lot to see and do here. Top sights to see include the Magnificent Mile (a road through the heart of the city), the Art Institute of Chicago, Museum Campus, Wrigley Field, and Millennium Park. In addition there are some of the nation’s top restaurants here, Broadway-quality shows, and a hopping nightlife. For more pointers, check out this detailed free road trip plan that starts in Chicago before heading into Michigan.

Cross Country Road Trip

Ah, the state of great cheese and beer! If you want to hit another city on your cross country road trip, you can always ride up the coast to Milwaukee, visit the Miller Brewing Company, the city’s well-known art museum, the kick-butt Harley-Davidson Museum, and "The Domes" Conservatory. For those of you ready to skip another city and see some beautiful countryside, the rest of the route is for you (those of you visiting Milwaukee can double back and catch up afterward). Don’t worry, there’s beer to be found on this hit list, even outside of Milwaukee.

  • Lake Geneva – Known as the Newport of the Midwest, this is beautiful lake is more than a summer getaway; it’s a chance to rub elbows with the rich and see their lifestyles up close. A little under two hours drive from Chicago, this city has been a summer home for its elite since the Great Chicago Fire drove them to seek refuge there. Take one of the mansion tour cruises of this lake and find out all about the sprawling estates that line this lake while getting a chance to get out on the water. Next, walk along the Shore Path (like the Cliff Walk in Newport) and literally walk through the mansions’ back yards! Stay overnight in this chi-chi resort area at one of the inns, B&B’s, or resorts – there are cheaper options for those on a budget, too.
  • Historic Auto Attractions, Roscoe, IL – Head southwest along either one of the interstates or back roads and hit the small town of Roscoe, IL (just over the border) to see a real road-tripper attraction: Historic Auto Attractions. This museum is must-see on your cross country road trip – it’s got the station wagon from National Lampoon’s Vacation, Bonnie and Clyde’s hats, Evita Peron’s limousine, and much much more! RoadsideAmerica wrote a great review (opens in new window) of this museum created by an ex-auto assembly worker with a fetish for memorabilia (and a love of sharing his enormous collection).
  • Wisconsin Cheese Country (and BEER) – Head north to Beloit (straddles WI and IL) and then west again on Rt. 81. to the town of Monroe and visit the Chalet Cheese Cooperative. You’ll be riding through some beautiful hill-country with lots of picturesque farms dotting the countryside. These farms are mostly dairy farms and almost all owned by the descendents of the Swiss immigrants who settled in the area. Go for a tour at the Cooperative and find out all about making cheese at the Historic Cheesemaking Center. There are plenty of cheese shops – be sure to stop by and sample (and buy) their wares for some great snacking. Come on – you’ve got room in your cooler! Next, head north on Rt. 69 to New Glarus to get a real taste of the Swiss community of this area. From the Swiss architecture to the cuckoo clock stores, this town is as Swiss as you’re going to get on this side of the Atlantic. Be sure to visit the Swiss Historical Village – many say this village reminds them of villages in Switzerland that they’ve visited. Next, stop by New Glarus Brewing Company for some real Wisconsin beer (it’s only sold in this state and it’s won many awards, Spotted Cow being the favorite).
  • Great River Road – It wouldn’t be a true cross country road trip if you didn’t ride along the Great Mississippi River for a piece. Ride up Rt. 69/92 and then head west on Rt. 151/18. The road will become primarily Rt. 18 and you can just follow it right into Prairie du Chien, WI, a charming town with lots of Victorian houses. The ride up along this route (Rt. 35) is gorgeous – that’s probably why it’s an official scenic byway! Ride up along this mighty river and watch river traffic, see towering bluffs, view charming small towns, and end up in La Crosse for the night. If you have time, book a cruise on one of the famous Mississippi River riverboats (paddlewheel and steamboats both) that still operate out of this town.
Minnesota, a state known for its bitter winters and friendly-but-guarded people lampooned in movies like Fargo, is the birthplace of dreamers who make big things happen. It’s amazing how so many remarkable people came from this state including Judy Garland, Charles and William Mayo (founders of the Mayo Clinic), Bob Dylan, and Charles Shultz to name a few.

Continue your cross country road trip headed northwest along the Mississippi before seeing a real road trip attraction (hint: it was suggested as a sight to see in National Lampoon’s Vacation.)(Are you starting to get the feeling that I like that road trip movie just a little?)

  • Great River Road Continued – The road crosses over the river and state lines and becomes Rt. 61. See more of the beautiful sandstone bluffs as well as all of the picturesque towns that dot the riverside.
  • Twin Cities: Minneapolis-Saint Paul – This is the capital of the arts in the Midwest (not counting Chicago) so be sure to stop and see a play or visit a museum in one of these two competing cities (hey, competition can bring out the best in people – bring it!). Saint Paul is known to be more of a fun city to stroll around (and get lost) in, while Minneapolis has a typical grid-pattern for easier navigation. One must-see on your cross country road trip is the Mall of America in nearby Bloomington. This is much more than just shopping. There’s the largest indoor theme park in the U.S., miles of shops and restaurants, an aquarium, a dinosaur museum, and even a chapel for an impromptu wedding.
  • World’s Largest Ball of Twine, Darwin, MN – Head west out of Minneapolis and into lake country – Minnesota is known as "The Land of 10,000 Lakes" and you’ll see why as you drive into this beautiful lake-dotted countryside. Stop in Darwin to see this town’s claim to fame: the largest ball of twine in the world rolled by one man (Francis Johnson). It has its own gazebo in the center of town – Clark Griswold would love it!
South Dakota
There are a lot of revered road trip sights in South Dakota – ones you usually think about when planning a cross country road trip. I mean, who hasn’t imagined stopping at Mount Rushmore for a photo op or wanted to see a real Wild West town or dreamed of viewing beautiful formations in the desert? Well, they’re all here in the western part of South Dakota! To get to the area with all the goodies, you’ll probably take two days, so stop overnight in the town of Sioux Falls and visit Falls Park as well as the fun-for-all-ages Outdoor Campus (the butterfly garden is great!).
  • Badlands National Park – "Otherworldly" and "supernatural" are words commonly used to describe this outstanding park featuring rock-hard sediment formations. Whether you get out and hike, or just drive the Loop Road that provides spectacular vistas throughout, you’ll be dazzled. I highly recommend you get out at every stopping point, though – there’s nothing like it in the world. Keep your eyes peeled for prairie dogs popping up here and there; there are tons of them living here in their underground homes.
  • Wall Drug Store – Just outside of the park, this famous-for-being-famous store is really like a mini-mall, but one of such hokeyness and created with such a sense of fun, it’s a must-see on your cross country road trip. Take a gander at the huge historical photo collection, laugh at the snorting animated T-Rex and listen to a choir of mechanical cowboys sing "Tumbling Tumbleweeds". This is a great place to get your South Dakota road food, too!
  • Mount Rushmore National Monument – See the much-photographed sculptures of the faces of four famous American presidents: Washington, Jefferson, Lincoln and Roosevelt. Carved into the side of a mountain, this monument took 14 years to complete and has been featured in movies, notably North by Northwest directed by Alfred Hitchcock
  • Crazy Horse Memorial – Native Americans’ retort to Mount Rushmore, this sculpture of Chief Crazy Horse is enormous – even bigger than the presidents down the street and is a work in progress. Currently, only the head is 100% complete, but it is majestic. A smaller version is provided to show how the finished project will look (all I can say is "Wow!")
  • Deadwood, SD – See a Wild West town so wild, even "Wild Bill" Hickok couldn’t handle it and was shot dead while playing cards in Saloon No. 10. This town still retains the feel of its lawless times with its many casinos, saloons, and restored old buildings. Multiple efforts have been made to keep history alive including regular reenactments of Wild Bill’s murder and the trial that followed.
Your cross country road trip isn’t over yet – you’ve still got to get to the coast! In Part III of this cross country road trip, you’ll travel through Wyoming, Idaho, and Washington all the way to Seattle.

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