This unforgettable road trip into the “Wild West” weaves you north from Denver, Colorado upwards into Wyoming, Nebraska, South Dakota, and North Dakota. Across this ~1,200-mile road trip, you will drive through flat and barren land, rugged terrain with diverse and dramatic rock structures, small towns with populations less than 500 people, mountains, national monuments and parks, and miles upon miles of unsettled wilderness. Seemingly countless bison, deer, elk, prairie dogs and other wildlife roam freely. You may even see badgers, bighorn sheep and wild horses.

Midwest Road Trip Itinerary and Travel Guide
You’ll drive over 1,200 miles across the Midwestern United States, encountering fascinating sights and experiences along the way.

Travel Tips and Practicalities

Flying into the Denver International Airport (DEN) might be your best option as it is easily accessible from many cities and is just over 90 minutes from Cheyenne. Fly home from Fargo, North Dakota’s Hector International Airport (FAR). Fargo may be harder to find direct flights, but you can also search other nearby airports, or continue onward to Minneapolis and fly home from Minneapolis-Saint Paul International Airport (MSP). Check for the best current flight deals, airports and timing options right here depending on your location.

Renting a car to navigate this journey will be the most efficient (unless you’re a local or driving long distance), but be prepared for a probable one-way fee. The driving is part of this trip. Enjoy it. Take your time and be swept away by the vast changing landscapes.

Many restaurants and hotels located in the path of this itinerary are seasonal. If you travel during the off-season, there may be limited hotel and/or restaurant options, but you may enjoy the sites without a crowd.

This itinerary suggests a minimum of 11 nights, but could easily be spread out over 3 weeks. This is a beautiful part of the United States. If you have more time, extend your stay at these stops and/or add more national parks and nearby outdoorsy adventures.


Winetraveler Tip: With the constantly changing COVID-19 travel restrictions and ordinances, check the current status of closures and restrictions that may apply along with CDC guidelines before embarking. Book fully refundable accommodations and/or fares whenever possible.


Stop 1: Cheyenne, WY (1 Night)

Cheyenne, the capital and most populous city of Wyoming exudes a quaint old western town charm. The city, founded in 1867, was initially populated by many employees of the Union Pacific Railroad busily constructing the railroad that would bridge together the east and the west. Despite obstacles caused by the dramatic and steep Rocky Mountains, the railroad connected with the Central Pacific Railroad in 1869 forming the first transcontinental railroad in the US.

History lovers and those fascinated by trains should head over to the Cheyenne Depot Museum and then the small Holliday Park to see the historic Big Boy Steam Engine, No. 4004. There is a nice peaceful lake and a playground. The Big Boy Steam Engines, the world’s largest steam locomotive, was designed to pull heavy-loaded trains over the sharply angled ground between Cheyenne and Ogden.

While in Cheyenne, you’re sure to spot at least a few eight-foot-tall artsy cowboy boots painted by local artists. You could go on a boot-scavenger hunt and look for them all. Here is a brochure map to help. Looking for a place to stay? Here are some great hotel recommendations in Cheyenne.

Drive ~1 hour 40 minutes to Scotts Bluff. 

Midwest Road Trip Itinerary - Scott's Bluff
Image courtesy Lenore Parr.

Stop 2: Scott’s Bluff National Monument, NE (1 Night)

Scott’s Bluff, in Gering, Nebraska, is immediately recognizable due to its height, size, and dominance popping 800 feet above the surrounding flat countryside. You can drive right up the bluff, through 3 tunnels, and then follow a short trail to a lookout spot with expansive views of the countryside. If you’re itching for more, peruse more trails on the park’s website.

Historically, Scott’s Bluff was used by Sioux Indians to chase and hunt buffalo. It served as an important landmark for many emigrants traveling through the Oregon Trail, California Trail, and the Pony Express Trail from 1843 to 1869. There are pioneer wheeled wagons on display with Scott’s Bluff in the background giving you the Oregon Trail vibe.

Take a look here for accommodation suggestions near Scott’s Bluff.

Drive ~30 minutes to Chimney Rock.


Stop 3: Chimney Rock National Historic Site, NE

Chimney Rock, in Bayard, Nebraska, is an iconic landmark of Nebraska and the American West. It is a giant pillar of rock protruding upward from the flat surface like a giant chimney. It’s believed to have been the most mentioned and recognizable landmark from the many emigrants along the Oregon Trail, California Trail, and Mormon Trail. It was a symbol of westward expansion. Search here for accommodation options near Chimney Rock.

Drive ~2.5 hours to Wind Cave National Park.

On the way to Wind Cave, consider stopping at the Mammoth Site, an indoor paleontologist site/museum where many mammoths have been unearthed.

Visiting Wind Cave National Park on a Midwest United States Road Trip
Boxwork is a unique geological formation that can be found underground in Wine Cave National Park. Image courtesy iStock.

Stop 4: Wind Cave National Park, SD

At Wind Cave National Park in South Dakota, countless wildlife roam the expansive 28,000 acres of scattered hills. Bison, deer, and elk are plentiful. The prairie dogs are so numerous, in some areas, it looks like the earth is moving as they scurry around. Be on the lookout for badgers. Enjoy the scenic drive of the beautiful terrain and pick the hiking trails that most interest you.

Below this extraordinary land is a vast cave. Tours of the cave range from 1 hour to 90 minutes and involve walking up and down quite a few stairs. The cave tours are presently suspended due to elevator repairs, but check back on the park’s website because hopefully, the caves will reopen by the time you get there. Here is a list of hotel recommendations near Wind Cave.

Drive ~40 minutes to Crazy Horse and Mount Rushmore. Consider taking a slightly longer route and driving through Custer State Park (or stay there for a while).

Road Trip to Mount Rushmore Travel Guide
Image courtesy Lenore Parr.

Stop 5: Crazy Horse Memorial and Mount Rushmore, SD (2 Nights)

Discover colossal art carved into mountains by visiting the Crazy Horse Memorial and Mount Rushmore National Memorial. Both are located in the Black Hills regions of South Dakota and are only ~17 miles apart. Hotel recommendations are found here.

The construction of the Crazy House Memorial, depicting an Oglala Lakota leader and war hero, Crazy Horse, started in 1948. The carving is far from finished. The face towers 87 feet. To put this size in perspective, the carved faces at Mount Rushmore are ~60 feet long. Once completed, it will be the world’s largest mountain carving.

Mount Rushmore, built between 1927 and 1941, is a well-known larger than life sculpture carved into the mountain depicting the faces of four US presidents: George Washington, Thomas Jefferson, Abraham Lincoln, and Theodore Roosevelt. As you approach the monument, state flags stand proud on tall columns with the date the state joined the union. Take the 0.6 mile-long trail with 422 steps to get a closer glimpse of the sculpture.


Winetraveler Tip: Return to Mount Rushmore at night to admire the faces illuminated in the darkness.


Drive ~90 minutes to Badlands.

Ultimate Midwest & Dakotas Road Trip Itinerary & Travel Guide | Badlands National Park
The Badlands offers a unique landscape that is especially breathtaking at sunset. Image courtesy iStock.

Stop 6: Badlands National Park, SD (2 Nights)

The Badlands, spanning 244,000 acres, is home to semi-desert scenery, grasslands, multi-colored layered rock formations, valleys, steep canyons, and plentiful wildlife. The Badlands formed by soft sedimentary rock being eroded by the dry climate. Numerous bison, deer, and antelope graze. Prairie dogs scurry in and out of their underground holes, seemingly by the thousands. You may even see a herd of bighorn sheep and rams.

As you make the 31-mile loop along the Badlands Loop State Scenic Byway, there are plenty of overlooks and trails to choose from to stretch your legs and be closer to the natural rugged beauty. Driving along the winding roads is remarkable. Each stone structure is unique. The surrounding barren plains make the incredible buttes, cliffs, and multi-colored spires appear even more impressive.

Hiking, biking, and horseback riding will keep outdoorsy spirits engaged. Admire the change in colors of the rock formations by catching it during sunrise and sunset. Make sure to look up in the sky to admire the starry nights. Check all things to do on the park’s website here. Take a look at hotel options in The Badlands here.

If you stay in Wall, stop at the Wall Drug Store. It’s a neat place that has grown quite a bit since its beginning in 1931. It takes up a whole block and has a drug store, café, and a small mall with various shops.

Drive ~2.5 hours to Devil’s Tower


Stop 7: Devil’s Tower National Monument, WY (1 Night)

Devil’s Tower is a giant rock tower soaring ~867 feet high from summit to base in Wyoming. It’s a sacred site to many Native Americans, and the first national monument in the US established in 1906. Follow the 1.3-mile loop trail around the tower and gain an appreciation of the tower’s width. Native American prayer clothes are attached to trees along the trail. Keep your eyes out for deer and prairie dogs. The National Park Service’s website lists and describes four more hiking trails. Here are some hotel options to consider near the park.

Drive ~3.5 hours to Theodore Roosevelt National Park.

Midwest, North Dakota and South Dakota Road Trip Itinerary and Travel Guide | Theodore Roosevelt National Park
Theodore Roosevelt National Park is an outdoor lover’s paradise. Image courtesy Nathan Wasylewski / Stock.

Stop 8: Theodore Roosevelt National Park, ND (2 Nights)

North Dakota, an underrated state, has more to offer than just flat empty fields, and even the expanse of those are beautiful. Visit Theodore Roosevelt National Park and discover why Theodore Roosevelt fell in love with this state. The rolling grasslands, jagged canyons, buttes, open plains, and multi-colored badlands in all directions appear endless. The vast unsettled wilderness is awe-inspiring. This rugged landscape inspired Theodore Roosevelt to focus his policies on conservation after becoming America’s 26th president.

While the park is fairly remote, it’s an easy park to visit once you’re there, even if you spend no time charting out what you want to do ahead of time. Driving along the winding scenic path through the park while stopping at many lookout spots is fabulous. Drive carefully as wildlife is abundant. Herds of bison, wild horses, bighorn sheep, elk, deer, countless prairie dogs, and many more animals make their home here. Pack a picnic basket, pick your favorite overlook spot, and have a picnic while soaking in views capable of taking your breath away.

Plentiful hiking trails from easy to strenuous levels await and are listed and described on the park’s website. Biking, horseback riding, and fishing (with a license) are all possible. Click here for our recommendations on the best hotels near the park.


Winetraveler Tip: While bison may appear gentle and passive, they are extremely dangerous to humans. Always be aware of your surroundings. Walk slowly around any bends with blind corners and maintain a safe distance.


Final Stops (2-5 Nights)

Appreciate the grand openness of North Dakota’s landscapes by driving eastward across the length of the state. Stop, rest, and explore with overnight visits in the cities of Bismarck and then Fargo. Check here for hotel options in Bismarck as well as Fargo

Consider extending your trip and driving an additional ~3.5 hours (250 miles) to Minneapolis, Minnesota. As you drive diagonally down the state, you will soon realize that its nickname, “Land of 10,000+ lakes” must be accurate. It feels like there’s a lake everywhere you turn the entire drive.

For those traveling with kids, take them to the Mall of America, featuring a large indoor theme park. There’s zip lining, large slides, a Ferris wheel, merry go round, shops too, and so much more. If you’re looking for somewhere fun and outdoorsy during your stay in Minneapolis, check out the 193-acre Minnehaha Park and admire the beautiful 53-foot Minnehaha Falls.

If you’re looking for more things to do throughout the U.S., be sure to browse these other travel guides or download our free app.


Get Articles Like These Directly in Your Inbox!

Subscribe to Winetraveler and receive notifications when new articles are published. It's free!

Leave a Comment, Ask a Question or Share a Review

    ABOUT THE AUTHOR

    Lenore Parr is a commercial bankruptcy attorney and stay-at-home-mom with a passion for adventurous and family-based travel with her husband and children (4yo and 1 yo). She has traveled with the kid(s) to 34 states and 23 countries.

      Send this to a friend