Last Updated on: 28th August 2025, 01:29 pm
Known for their remarkable badlands, massive sculptures, and ample wildlife, the Dakotas are gradually becoming known as must-visit destinations for both nature and history lovers. But if you’ve never been to the area and aren’t sure how to go about planning a visit, this two-week North and South Dakota road trip itinerary has you covered.
Between the two states, South Dakota – the home of Mount Rushmore – seems to be a lot more popular when it comes to tourism. As such, many online itineraries solely focus on that state. But North Dakota’s Theodore Roosevelt National Park is so incredible that it would be a shame to come out to this part of the country and miss it.
In any case, both North and South Dakota are rather geographically isolated, and figuring out how to get in and out of the region can be a challenge. This is a topic you’ll learn more about over the course of this guide.
A 2-Week North & South Dakota Road Trip Itinerary
- Day 1: Arrive in Custer
- Day 2: Wind Cave National Park
- Day 3: Custer State Park
- Day 4: Custer State Park + The Crazy Horse Memorial
- Day 5: Jewel Cave National Monument (or Anything You Missed)
- Day 6: Mount Rushmore, Onward to Wall
- Day 7: Badlands National Park
- Day 8: Badlands, Onward to Deadwood
- Day 9: A Day Trip to Devils Tower
- Day 10: Spearfish Canyon and Bear Butte
- Day 11: Around Deadwood, Onward to North Dakota
- Day 12: Theodore Roosevelt National Park (South Unit)
- Day 13: Theodore Roosevelt National Park (North Unit)
- Day 14: A Day Trip to Makoshika State Park
- Day 15: Moving On
Day 1: Arrive in Custer
Whether you’re arriving in South Dakota from another state as part of a longer road trip or flying directly in, Custer serves as a great introduction to the Black Hills area.
In either case, you’ll likely need to rent a car. Fortunately, no special vehicle is required to carry out this itinerary, and you should be just fine in a regular sedan.
Custer is the base for Custer National Park, Wind Cave National Park, Mount Rushmore, the Crazy Horse Memorial, and Jewel Cave National Monument, so you’ll want to spend at least several nights in town.
If you’ll be driving here from the Denver/Rocky Mountain area, you can visit some interesting geological sites in western Nebraska along the way.
In that case, you could even do some hikes at Wind Cave National Park as you make your way to Custer in order to free up some time for the next day.
For those arriving by plane, the nearest airport is the Rapid City Regional Airport, with flights to and from Denver, Minneapolis, Dallas/Fort Worth, and Las Vegas. You can then drive to Custer from Rapid City in under an hour.
Note that the following ideas for how to spend your time in Custer can be done in any order you like. If you’re planning on doing cave tours at either Wind Cave National Park or Jewel Cave National Monument, then it would be wise to plan the rest of your itinerary around that.
WHERE TO STAY IN CUSTER: While Custer may be a small town with under 2000 residents, its proximity to so many prominent landmarks makes it a popular place for long stays.
There are plenty of hotels to choose from, but I ended up staying at the Super 8 and have no complaints about it. I found it to be a quiet hotel and I slept well each night.
Other popular options in the area, meanwhile, include the Comfort Inn & Suites, the Holiday Inn, and the Rocket Motel.
Day 2: Wind Cave National Park
As its name suggests, the most popular activity at South Dakota’s Wind Cave National Park is visiting the Wind Cave. The park is said to house one of the world’s longest and most complex cave systems, and its especially known for its unique formations like boxwork.
Though the cave was closed for a while due to the construction of a new elevator (as it was during my visit), it’s already open at the time of writing.
Wind Cave has no less than six different tours to choose from, three of which – the Garden of Eden Tour, Natural Entrance Tour, and Fairgrounds Tour – can be booked in advance. The others, meanwhile, are first-come, first-serve. You can make reservations here.
Unfortunately, not having been able to do any of the tours, I can’t provide recommendations. But the Fairgrounds Tour is the longest of them all, lasting 90 minutes.
Depending on when your tour or tours are scheduled for, you should also set time aside for an above-ground hike either in the morning or afternoon.
The best hike in the park is the Lookout Point Trail & Centennial Loop hike, which you can learn more about in our dedicated guide. It should take about two hours to complete, though you may need to make some detours if you encounter bison on the trail!
Day 3: Custer State Park
The massive 71,000-acre Custer State Park is arguably South Dakota’s top attraction – perhaps even outshining its two National Parks.
In addition to some epic hikes, the park is also known for its three scenic drives. As such, you’ll want to set at least two full days aside for Custer State Park. But exactly how you go about things will depend on how much of a hikers you are, and of course, the weather.
When it comes to must-see natural landmarks, visitors shouldn’t miss Sylvan Lake, Black Elk Peak, Little Devils Tower, and the Cathedral Spires. There are multiple ways to see them, such as visiting each landmark separately as its own out-and-back hike.
But all the major landmarks are connected via the area’s extensive trail system and can be combined as part of one long loop hike which is about 8 miles long in total. All in all, expect it to take you somewhere between 4-6 hours. You can learn more about it in our dedicated guide.
If that sounds too daunting, then don’t worry. This South Dakota road trip itinerary leaves you enough time to do everything separately on different days.
Following your first day of hiking, you can then easily drive back to town via the stunning Needles Highway, a 14-mile road that’s part of South Dakota Highway 87. You can find the entrance right by Sylvan Lake.
Along the road, you’ll encounter numerous narrow tunnels and some of the park’s most picturesque needle-like granite formations.
*Note that Custer State Park passes, which cost $20 at the time of writing, are valid for 7 consecutive days.
Day 4: Custer State Park + The Crazy Horse Memorial
How you spend your second day at Custer State Park will largely depend on what you did the previous day. For example, if you still haven’t seen Little Devils Tower or the Cathedral Spires, consider hiking there on this day.
Another relatively short hike to consider is the Sunday Gulch Hike, an exiciting hike that involves grabbing onto metal railings as you walk over large granite boulders. You can find the trailhead near Sylvan Lake, while the total hike should take you around 2-3 hours.
In any case, you’ll want to set some extra time aside on this day, as when finished with Custer State Park, you can go spend a few hours at the Crazy Horse Memorial.
The memorial is a quick fifteen-minute drive from central Custer, while you can see everything there is to see in a few hours. Note that the experience is quite different from visiting Mount Rushmore.
Presently, the Crazy Horse Memorial is largely just a complex of museums from which you can only see the monumental sculpture from afar. You can, however, pay $5 extra for a bus ride that takes you closer to the monument. But you won’t be able to linger for long.
Day 5: Jewel Cave National Monument (or Anything You Missed)
Days 2-4 mentioned above already cover the essentials of the Custer area. But if time allows, it would be wise to set aside an extra day to see anything you may have missed.
This extra day will also come in handy if you encountered bad weather. But if you’re in a rush, you can remove this day from your North and South Dakota road trip itinerary.
If you already accomplished everything mentioned above, here are some additional suggestions:
In the immediate Custer area, be sure to drive Custer State Park’s Wildlife Loop. As the name suggests, the 18-mile-long scenic drive is considered one of the best places to see wildlife at Custer State Park. Including stops, expect it to take you about two hours to complete.
You could also spend some time relaxing in central Custer itself. While the Old West town doesn’t have nearly as much going on as Deadwood (more below), the town center is a good place for souvenir shopping You can also check out the 1881 Courthouse Museum.
There are still a few more attractions to see outside of town. Jewel Cave National Monument is 13 miles west of Custer. Similar to Wind Cave National Park, there are multiple cave tours to choose from. But if you’re visiting during peak summer season, you should make your reservation well in advance.
Another nearby attraction is the Mammoth Site, a paleontological site where dozens of mammoths were discovered. Though I didn’t visit, aside from paleontology enthusiasts, the site seems largely geared toward families with young children.
Day 6: Mount Rushmore, Onward to Wall
Mount Rushmore is not only one of South Dakota’s most popular attractions, it’s one of the most iconic landmarks in the entire country. It was construction of this monument, in fact, that largely gave birth to South Dakota tourism in the first place.
While you could simply show up, look at the monument, and leave, seeing everything there is to see could take up to a few hours.
But first, how to get there from Custer? After packing up your things and loading your car, you have two different options. While the quickest route only takes half an hour, it’s well worth taking a detour to get there via Iron Mountain Road.
This will add an extra thirty minutes or so to the journey, but the scenic route allows you to see the carvings from a distance from various vantage points. You can even view the presidents through rock-cut tunnels!
Note that if you’re following this itinerary, you won’t be able to experience the nightly Evening Lighting Ceremony which begins at 20:00. If that’s a big priority for you, then consider visiting Mount Rushmore the previous day instead.
Finally, when finished with your visit to Mount Rushmore, it’s time to move onto Wall, the nearest town to Badlands National Park (you could also choose Rapid City as your base – more below).
Wall is also known for Wall Drug, a huge shopping complex that contains multiple souvenir shops, cafes and yes, a drug store. You’ll find signs along the highway promoting it all over the state.
After checking in, consider enjoying sunset at the Pinnacles Overlook within the park.
WHERE TO STAY NEAR BADLANDS NATIONAL PARK: As mentioned, the closest town to Badlands National Park is Wall, South Dakota, which is just 15-25 minutes from the park (depending on which entrance you start at).
There are a few different options to stay at in Wall, but it’s best to avoid America’s Best Value Inn Wall. Unfortunately, the building is so poorly made that if you’re on the ground floor, the entire room will shake whenever your neighbors walk!
Just next door to America’s Best Value Inn is a Travelodge by Wyndham. While nothing fancy, Travelodge is usually pretty consistent when it comes to quality.
Staying in Wall is generally pricier than other options. The next best option would be Rapid City, which is just about an hour from the Pinnacles Entrance Station.
Popular options there include Country Inn & Suites by Radisson, Best Western Plus Rapid City Rushmore, and Staybridge Suites Rapid City.
If budget is a concern, you should be fine staying in Rapid City, especially considering how the sunrises and sunset at Badlands don’t quite live up to the hype. Just be sure to get an extra early start each morning.
Day 7: Badlands National Park
Despite its remoteness, Badlands National Park attracts around 1 million visitors each year. And for most visitors, the sights and hikes along Badlands Loop Road will be their first introduction to the park.
Both ends of the Badlands Loop Road are connected to Highway 90, and it can be driven from either direction, either starting with the Big Badlands Overlook or with the Pinnacles Overlook. There are positives and negatives to either approach.
The main advantage of starting from the Big Badlands Overlook is that it’s nearby a large parking area that’s home to multiple trailheads. The lot can already fill up by late morning, so it’s helpful to get there early to beat the crowds.
On the other hand, by starting at the Pinnacles Overlook, you can enjoy the Pinnacles in the morning when the lighting is best. And by finishing at the Big Badlands Overlook, you can proceed right to the Minuteman Missile National Historic Site further north.
In any case, visiting all the hikes and overlooks along the road will take most of your day. Be sure to check our Badlands Loop Road guide for the full details.
Day 8: Badlands, Onward to Deadwood
While many visitors simply explore Badlands Loop Road before moving on, the lesser-visited backcountry of the park is arguably more interesting.
First of all, you’ll want to pack up your things before heading out in the morning, as this day of the itinerary ultimately has you checking into your hotel in Deadwood.
First, head down Conata Basin Road to freely explore the Deer Haven area. It’s less of a proper trail and more of a general area that visitors are allowed to freely explore.
Then head over to Sage Creek Rim Road, which starts just next to the Pinnacles Overlook. As with Badlands Loop Road, it’s home to numerous overlooks, some of which are among the park’s best.
Much of it is unpaved, though the dirt portion of the road is only 6.5 miles long before it eventually becomes paved again.
Following the road all the way, you’ll eventually end up in the ghost town of Scenic.
Next, past the town of Scenic, head south down Bombing Range Rd. About five minutes later, you’ll reach the turnoff for Sheep Mountain. The unpaved Sheep Mountain Road will take you up atop the formation known as Sheep Mountain Table. It’s arguably one of Badlands National Park’s most impressive views.
When finished, head all the way to the White River Visitor Center. From there, you want to head west along Cuny Table Road before eventually turning right to head north along Red Shirt Table Road.
The Red Shirt Table Overlook is about 25 minutes past the White River Visitor Center. This remote overlook easily rivals – or even surpasses – the various overlooks along Badlands Loop Road or Sage Creek Rim Road.
From here, it’s finally time to say goodbye to Badlands National Park and head toward Deadwood, which is about 90 minutes away. But you’ll likely be hungry by this point, so you might want to stop for a meal in Rapid City along the way.
WHERE TO STAY IN DEADWOOD: Not only is Deadwood a destination in its own right, but it also makes for a great base for various destinations that we’ll be covering below. As such, you’ll want to stay at least several nights.
I stayed at the Deadwood Gulch Resort which I have no complaints about. While not in the town center, it was an easy drive away, while you can also take a shuttle to town if you don’t feel like driving (or parking).
I had a peaceful and quiet stay, though my room was on the upper floor and not overlooking the parking lot. I’d imagine that guests staying on the ground floor facing the lot might have to deal with noise.
Other highly-rated, more central options include Four Points by Sheraton Deadwood, Celebrity Hotel, and Travelodge by Wyndham.
Day 9: A Day Trip to Devils Tower
Though located in the state of Wyoming, we’ll nevertheless be including Devils Tower in this North and South Dakota road trip itinerary. Not only is it an easy 90-100-minute drive from Deadwood, but the unique natural landmark shouldn’t be missed by anyone coming to the region.
The ominously-titled Devils Tower, known for its unique vertical stone columns, was declared the first-ever US National Monument by President Theodore Roosevelt in 1906.
The Devils Tower National Monument features multiple hiking trails that allow visitors to appreciate the mysterious monolith from different angles. All in all, think of visiting Devils Tower as a half-day trip.
It’s possible to combine Devils Tower with one of the attractions featured in Day 10 of this itinerary, such as Spearfish Canyon. But considering how you probably arrived in Deadwood late the previous day, this would be a good day to become acquainted with the town.
Deadwood is widely regarded as one of the best-preserved Old West towns in America. In addition to its historical architecture and beautiful surroundings, many come to learn about its infamous former residents, such as Wild Bill Hickok and Calamity Jane.
Rather than a single day dedicated solely to exploring Deadwood, this itinerary allows you to experience bits and pieces of the town before and after your other excursions. All in all, you should have just enough time to see everything – or at least most of it.
Be sure to check out our guide to the top things to do in Deadwood for a comprehensive list of activities you shouldn’t miss.
Day 10: Spearfish Canyon and Bear Butte
This day takes you to two remarkable natural landmarks: Spearfish Canyon and Bear Butte State Park. As mentioned, you could also visit one of them on Day 9 instead if you prefer.
Situated along a 19-mile stretch of South Dakota’s Highway 14A, the Spearfish Canyon Scenic Byway is fast gaining a reputation as one of the state’s top scenic drives. From Deadwood, it’s about a 30-minute drive to the town of Spearfish, from which you can access the Spearfish Canyon Scenic Byway from the north.
Much of the area’s beauty can be enjoyed from the road and its numerous pullovers. But various landmarks like caves and waterfalls need to be hiked to. All in all, it should only take several hours to complete all the overlooks and hikes.
When finished, you can make a brief stop in Deadwood before moving on to Bear Butte State Park. Located just outside the city of Sturgis, Bear Butte State Park is part outdoor, part cultural experience.
In addition to learning about Native American history at the Educational Center, visitors can climb Bear Butte itself – a lone mountain that has long been sacred to the Lakota and various other tribes.
The hike to the top is known as the Summit Trail. It’s about two miles long with roughly 1000 feet of elevation gain. Expect the roundtrip hike to take you from around 90 minutes to two hours, while the difficulty level could best be described as moderate.
At the time of writing, Bear Butte State Park costs $8 per vehicle.
Day 11: Around Deadwood, Onward to North Dakota
As mentioned, there’s plenty to do around Deadwood, and you can experience most of the town in bits and pieces over the course of several days. Day 11 of this itinerary has you start by seeing anything that you have yet to see before heading north.
In my case, I spent my final morning in Deadwood visiting the Mt. Moriah Cemetery, followed by an excursion to the Mt. Roosevelt Friendship Tower.
After finishing your explorations of Deadwood, it’s time to head north to North Dakota. Your final destination will be one of the towns near Theodore Roosevelt National Park – either Medora or Dickinson.
If you were to drive from Deadwood to Medora nonstop, it would take a little over 3.5 hours. But if you’d like to break up the journey, consider taking a detour to White Butte, North Dakota’s highest point.
Hiking to the top of White Butte and back should only take about an hour roundtrip. Sure, it may be North Dakota’s highest point at 3506 feet above sea level, but the hike itself only has an elevation gain of 337 feet (103 m).
WHERE TO STAY NEAR THEODORE ROOSEVELT NATIONAL PARK: The closest town to Theodore Roosevelt National Park is Medora, a charming and well-preserved Western town. Hotels here, however, can be quite pricey. And there aren’t many options online other than AmericInn by Wyndham Medora.
The next best option is the city of Dickinson, about a 35-minute drive away. Dickinson is also about an hour and fifteen minutes from the park’s North Unit – not much further than the one-hour drive from Medora.
Dickinson is a rather unremarkable city of 25,000 people, albeit one that has plenty of shopping and dining options compared to Medora.
I stayed at the Microtel Inn & Suites by Wyndham which was fine for the price. Other popular options include the Holiday Inn and Hawthorn Extended Stay.
Day 12: Theodore Roosevelt National Park (South Unit)
Theodore Roosevelt National Park is a highly underrated park that many visitors find even more impressive than Badlands National Park. Its badlands are a lot more colorful overall, and its hiking trails are more exciting.
The park is divided into three different units: the South Unit, the North Unit, and the Elkhorn Ranch Unit. Considering how the ladder unit is difficult to reach and doesn’t contain much to see, most visitors skip it. Accordingly, we’ll be omitting it from this North and South Dakota Road Trip Itinerary.
Day 12 of this itinerary is dedicated to the park’s South Unit, which itself is divided into a few different sections. Those who start early enough should be able to explore both the Scenic Loop Drive and the Painted Canyon area in a single (albeit long and tiring) day.
Be sure to check both our guides to Painted Canyon and the Scenic Loop Drive for the full details.
Day 13: Theodore Roosevelt National Park (North Unit)
Even among those who do make it out to this remote part of North Dakota, not everyone ends up visiting the park’s North Unit. But not only does the North Unit have the park’s top hiking trail, its viewpoints also rival those of the more popular South Unit.
The entrance to Theodore Roosevelt National Park’s North Unit is about one hour from Medora and an hour and fifteen minutes from Dickinson. Turning off of the CanAm Highway, you’ll find yourself driving down Scenic Drive, the North Unit’s main (and really only) road.
As with the South Unit, there are numerous viewpoints and hiking trails to experience, though the North Unit is smaller overall. If you are at all a hiker, be sure not to miss the Caprock Coulee Trail – easily the top hike in the North Unit and in Theodore Roosevelt National Park as a whole.
This is a 4.1-mile (6.6 km) loop hike with an elevation gain of 584 feet (178 m). It could be considered moderate in difficulty, and it should take most hikers about 2-3 hours.
With its numerous overlooks and ever-changing scenery of otherworldly badlands, it’s arguably the best hike in the Dakotas (just edging out Custer State Park’s Black Elk Peak loop).
Don’t miss our standalone guide to the Caprock Coulee hike, in addition to our overall guide to the park’s North Unit.
Day 14: A Day Trip to Makoshika State Park
As with Devils Tower mentioned above, this is yet another day trip that takes you across state lines – this time to Montana.
At over 11,000 acres, Makoshika State Park, located just outside of Glendive, is Montana’s largest state park. ‘Makoshika’ is the Lakota word for ‘badland,’ and the park accordingly shares a lot in common with nearby Theodore Roosevelt National Park.
But despite a proposal in the 1930s, Makoshika was rejected by the National Park Service and instead became a state park. Nevertheless, Makoshika State Park should best be thought of as Theodore Roosevelt National Park’s unofficial ‘West Unit.’
In addition to thrilling hikes, Makoshika should also be of interest to dinosaur enthusiasts, as numerous species have been uncovered in the area.
Makoshika State Park has a lot to explore, and you likely won’t be able to complete 100% of the park’s trails within a single day. Though you can indeed complete the park’s most impressive trails as a day trip.
You can reach the park in about an hour from Medora or roughly 90 minutes from Dickinson.
Day 15: Moving On
One of the biggest challenges of a road trip through the Dakotas is figuring out how to get back home. If Theodore Roosevelt National Park will be your final stop, finding a flight onward can be difficult. The closest airport is in Dickinson, but it appears to only have a single route to Denver.
Otherwise, the nearest airport is Bismarck International Airport, which has flights to and from Denver, Chicago, Dallas, Las Vegas, Phoenix and Orlando.
At the opposite end of the state, meanwhile, is Fargo’s Hector International Airport. It has flights to and from Minneapolis, Denver, Chicago, Dallas, Las Vegas, Los Angeles, Orlando, and Phoenix.
Depending on your flight time, consider stopping at the Knife River Indian Villages National Historic Site during your journey east.
But what if you want to extend your road trip? After leaving the Theodore Roosevelt National Park area, it would be wise to spend a night in Fargo, which is perhaps best known for the movie and TV series of the same name.
From there, you can head into Minnesota and Wisconsin. While not among the country’s most exciting states, they each have some gems to explore.
For those heading west from North Dakota, on the other hand, you could finish your Day 14 excursion to Makoshika State Park by heading deeper into Montana. And from there, you could ultimately make your way to Glacier National Park, though planning for that park well in advance is imperative. (See our Glacier Planning Guide for more details.)
For those carrying out this itinerary in reverse and finishing in Custer, you could then proceed toward Rocky Mountain National Park, or perhaps west through Wyoming toward Yellowstone National Park.
