Trans South Dakota

A Different Kind of Bikepacking Adventure


The Black Hills. The Mickelson Trail. Mount Rushmore. Buffalo Gap Grasslands. Badlands National Park. Herds of bison. Wall Drug. Packrafting the Missouri River. Oh, and some bike riding. In just three long days, I experienced all of the above and more at the 2018 Trans South Dakota bikepacking event. 

Organized by adventurous couple Joe and Tina Stiller, the full Trans South Dakota is 740 miles from Beulah, Wyoming, to Sioux City, Iowa. Also on offer are a half-distance 350-miler and a 60-mile event. Each event is self-supported — it’s up to every rider to carry enough food and water to get safely from town to town. Many participants approach the event as a bikepacking race while others see it as a tough tour along a well-chosen route. In either case, once the clock starts, it ticks onward until the finish line is reached. There are no fixed stages or required daily mileages, only a series of checkpoints with associated cutoff times. 

Falling only two and a half weeks after I returned from 25 days on Tour Divide, I was happy to only ride halfway across the state, and I was lucky that my wife Kristen joined me. As we dug into the route — provided only to registered participants — we realized that bigger-mileage days would land us in towns each evening. So instead of packing camping gear, we booked motels. This kept our loads light, and, after a phone call to consult with Joe Stiller, we decided to take gravel bikes to move speedily along the dirt and gravel roads we would encounter for the majority of the route. But first we had to conquer the arduous initial 60 miles.

Joe and Tina Stiller have a lot of experience with multiday adventures. On their collective résumé are the Iditarod Trail Invitational, Baja Divide, Dirty Kanza, and bikepacking trips in Vietnam and Laos. Joe is also the man behind BarYak, a handlebar accessory that provides an easy way to carry lights, GPS devices, cue sheets, and bikepacking gear while also offering additional hand positions. I have reviewed one in the past, and while in South Dakota Stiller handed me the latest model and its associated accessories. Look for a review soon. Joe also acts a regional sales representative for Kokopelli packrafts and loves to take multimodal adventures. 

But back to those opening 100 kilometers — they were no joke. Almost the entire route is on dirt, but it’s the Black Hills that present a huge challenge for Trans SD participants. Climbing over and around them, the Stillers have pieced together a remarkably remote path through rough terrain. In some cases Forest Service roads climb to gorgeous overlooks while in other instances a narrow dirt path bisects meadows of waist-high tallgrass. A section along Iron Creek was particularly pleasant with splendid rock formations and cool water on offer, provided you carry a filter. Annie’s Creek Road climbs along the namesake creek and included several shin-deep water crossings. This led to a rocky hike-a-bike before dumping us out above a huge open-pit mine. 

The going was certainly tough, and it had us second-guessing our choice of bikes, their tall gearing, and 40mm tires. Others on mountain bikes — some on fat bikes — clearly reveled in this technical section, but we managed to pick our way through without incident. 

The end of the technical riding coincided with our arrival in Lead, South Dakota. There we made our way to a grocery, but just as we locked our bikes up outside, the skies let loose. After our meal, we donned rain jackets and made our way to the trailhead for the Mickelson Trail, a 109-mile rail trail that offers pleasant grades and beautiful views. At the trailhead we were greeted by the Stillers who had our $4 trail passes ready as well as snacks and drinks. Kristen, as the first female to reach the trailhead, won a belt buckle that celebrates conquering 10,000 feet of rocky climbing and 60 miles of incredible Wyoming and South Dakota backroads. 

While a few other competitors waited at the trailhead to see whether the weather would pass, we headed out. Our hotel was 40 miles away in Hill City, all of them along the Mickelson Trail and away from car traffic. Just as we rolled away, a hard rain began to fall. This was followed by hail, more rain, and some thunder and lightening. Thankfully the temperatures were warm and we had good rain gear. At one point we stopped to put on our rain shorts/knickers and saw that we had just missed golf-ball-sized hailstones. That served to slow our pace in hopes the worst of the storm would stay ahead of us. 

Despite the weather, the Mickelson Trail was a highlight for both of us. We laughed our way to Hill City, happy that the going was easier and our bellies were full. We plan on returning to the rail trail some day in the future. There were restroom and water stations, many with bike repair stands, every eight to 12 miles. 

We rolled into Hill City in a downpour and after checking into our hotel — and asking for extra towels — we spread out our gear so it would dry, ate a quick meal, and fell asleep to the sound of distant thunder. 

In the morning, blue skies and cool temperatures greeted us. We rolled out early, anxious to beat tourist traffic at Mount Rushmore. After an hour of easy riding and a short hike-a-bike, we rounded a corner and saw the iconic stone faces looking back at us. We snapped a few photos and posted them to social media, a requirement of the race that serves as a fun digital checkpoint. We would do it again later in the day as we entered Badlands National Park. 

After Mount Rushmore, we rode up the smooth pavement of the Pigtail Highway, a road with overpasses that circle back over themselves in the shape of, well, a pigtail. The early morning hours made for a quieter ride. 

Next up were some lovely dirt and gravel roads. We lost elevation as we rolled into Hermosa where a 24-hour truck stop acted as a welcome resupply. From there it’s 80 dusty miles to Wall, South Dakota. Kristen and I went heavy, carrying breakfast burritos, sandwiches, candy, energy bars, and five liters of fluids each. While the temperatures rose steadily, so too did the wind. Thankfully it was mostly a crosswind out of the north and helped cool us during our ride through the Badlands. At the entrance of the national park, we were surprised to once again see the Stillers and their Sprinter van. We took the pickles, Cokes, and ice they offered and then rolled onward. 

In the park Kristen stopped an overlook where we paused to feast on our breakfast burritos, Swedish Fish, and take on additional fluids. Just after we began pedaling again, we were slowed by a herd of bison crossing the road. Motorists clogged the road snapping photos. I chose to roll through slowly, using the cars as metal shields between us and the huge animals. 

That night in Wall, after showers and a change into casual clothes, we walked a few blocks to Wall Drug. We bought a couple items at the pharmacy and walked around, taking in the garish décor and examining the photos of the tourist trap’s owners. As our energy waned, we walked back to the motel, downed some snacks, and sacked out for the night. 

Our third day would be our longest at 140 miles, but it would also see us reaching our finish line. We also had to brave a long, 100-mile stretch without any food or water available save for knocking on the door of an area rancher. 

To try and beat some of the midday heat, we were rolling by 5:15 AM. It was wonderfully chilly out, and a superb sunrise started the day off right. After 40 fun miles that included some remote doubletrack, we arrived in Philip. We knew only of a convenience store and a Subway, and so we were delighted to see a quaint coffee shop as well. We shared an iced coffee as the day’s heat had already arrived. Next up was a stop at the convenience store for breakfast sandwiches and iced tea. We also topped up on food for later in the day, and I loaded my bike and pockets up with six and a half liters of tea, Gatorade, Coke, and water. 

The final 100 miles of our ride were not easy. The heat built steadily but didn’t hit triple digits as it had at the previous year’s event. Kristen and I were also lucky that the wind wasn’t any stronger. Instead a gentle crosswind kept the air moving and us reasonably cool. A long series of rolling hills marked the end of our tribulations. Cresting the last hill we had a gentle downhill to a paved highway. A few miles later we treated ourselves to a cold drink, a soft serve ice cream for me, and a root beer float for Kristen. We had reached Fort Pierre and the banks of the Missouri River. 

A few easy miles along a paved bike path guided us to the Oahe Downstream Recreation Area and the campground that was the midpoint of Trans South Dakota and our finish line. We arrived early in the afternoon to a lovely spot where we could shower, eat, drink, and, eventually, sleep. Joe and Tina showed up sometime later after escorting another participant down the river on a packraft. As we waited, other racers showed up. As they were still racing, we ceded our spots in the available packrafts so they could continue on toward the Iowa border. 

We set up our tent and called in an order for a couple of pizzas in town. After dinner and a few beers at the campsite, we settled in for the night. We woke in the morning eager for some time on the river. After breakfast burritos, lovingly made by Tina, we inflated a tandem packraft and paddled five miles downstream. Once ashore we were presented with finisher medals and stickers. 

We made new friends and took in an almost shocking number of historic sites and landmarks. The riding was tough but beautiful. And there are few things like experiencing the changes in a state’s topography as you cycle through it. 

If you’re looking for a fun yet challenging adventure, Trans South Dakota fits the bill. It ain’t easy, but that’s exactly the point. 

Nuts & Bolts 

Sign up:

Entry for the 2019 Trans South Dakota is open. Head to for details and pricing. 

The Bike: 

Although there was a wide array of bikes used during the event, I think a bike like Salsa’s Fargo or Cutthroat is close to ideal. If you’re technically savvy, a gravel bike can be nursed through the opening 60 miles. After that, the 40mm tires we rode really came into their own. 

You’ll want low gearing for the steep opening climbs and constant rollers of South Dakota’s plains. 

Perhaps most important is the ability to carry a lot of water. I had five water bottle cages on my bike, each carrying a one-liter bottle. In addition, I strapped a liter Gatorade to my seatbag and carried a 20-ounce bottle in my pocket for our final 100-mile stretch. Kristen chose to use three bottle cages on her bike and wore a hydration pack. 

To Camp or Not To Camp:

We were not the only participants to leave our camp gear at home. (We did camp at the start line and then the Stillers shuttled our tent and sleeping gear to the finish line. Thanks, Joe and Tina!) With careful planning and the ability to take on big daily mileages, you can stay in a motel or cabin each night. That said, Kristen and I each carried warm clothing and an emergency bivvy in case of unforeseen issues. Carrying gear slows you down thanks to the increased heft, but it does offer much more flexibility for when and where you sleep each night. 


Kristen and I drove to the event from our home in Colorado. We stopped in Spearfish along the way, collected a rental car, and drove it and our truck to our finish line in Fort Pierre. We paid for a few days in a campsite there so we could leave our truck. Then we loaded up the rental car and headed back to Spearfish. We rode the 15 miles to Beulah, Wyoming, where the race started. 

Alternatively, the Stillers offer a shuttle service and will connect racers who have similar travel plans so they can share rides to and from. 

Nick Legan is the Technical Editor of Adventure Cyclist. Follow his adventures at @nlegan.