2026 Family Motorcycle Trip Through Wyoming & South Dakota

If you follow us on Facebook, you already know we don't do "relaxing" vacations. This summer we loaded the motorcycles on the trailer, the kids in the truck, and set out to ride some of the twistiest, most scenic roads in North America. By the time we rolled back into Oklahoma, we'd logged almost 3,000 miles — and more "WOO-HOO's" than we could count.

We get asked a lot how we balance running a top-producing real estate business with adventures like this one. The honest answer? We plan hard, we work hard, and then we go all-in on making memories with our kids — because that's the whole point of building a business like ours in the first place.

Here's how the trip came together, and everything we got into along the way.

Six Months of Planning Before We Ever Hit the Road

Trips like this one don't come together overnight. We actually started planning nearly six months in advance, and the first order of business was making sure we had the right bikes for the job. Dirk already had a 2009 BMW GS F800, but we needed to find a motorcycle that could fit my inseam, be light enough to maneuver technical terrain, and beefy enough to eat highway miles while loaded with 2 people + all of our gear. After months of saving and searching, we finally added a new motorcycle to our garage... a nearly new 2024 Honda Transalp 750! Which meant we were ready to figure out how we'd actually get our bikes 900 miles to Wyoming.

We briefly considered riding the 2,000-mile round trip from Oklahoma to Wyoming and back on the bikes, but ultimately decided that our butts couldn't handle that kind of saddle time. The answer was a trailer, and we got lucky finding a nearly-new one for a great deal on Facebook Marketplace. Even though Oklahoma doesn't technically require a tag on a trailer like ours, we had it tagged anyway. We didn't want to take any chances getting pulled over out of state. From there, Dirk and our son Casper spent several days mounting tie-downs and building out the trailer so we could safely strap both bikes down for the haul.

Once the gear side of things was handled, we turned to the trip itself — mapping our route, watching the weather, and booking hotels along the way. The plan was to  meet up with Dirk's dad, Chuck, in Casper, Wyoming, where he'd join us on his own cruiser for the main ride through South Dakota.

The last piece of the puzzle was packing. With only one small pannier each to hold everything we needed for 10 days on the road, we had to get ruthless about what actually made the cut. Here's what each of us packed for a week and a half on two wheels:

• 2 pairs of jeans
• 6 shirts
• 10 undergarments
• 6 tall socks
• Hiking boots with ankle support
• 1 pair of tennis shoes
• 2 pairs of shorts
• Toothbrush
• 1 swimsuit
• 1 hat
• 1 pair of sunglasses
• Laptop
• Cell phone and charging cables

That last item is a bigger deal than it sounds. Even on a motorcycle trip through the middle of nowhere, we still make room to bring work with us on the road. In real estate, you never know when an offer is going to come in that needs to be reviewed, negotiated, or signed — and our clients deserve a responsive agent whether we're at our desk or somewhere in the Black Hills. A laptop and a charging cable earned their spot in the pannier right alongside the essentials.

After a few mishaps and a lot of trial and error, we finally hit the road — and it was worth every bit of effort.

Best Gear Upgrade: The Cardo PackTalk Edge

One of the best decisions we made before this trip was outfitting all of our helmets with the Cardo PackTalk Edge communication system, also available on Amazon. It completely changed the way we ride as a family. In all our years on motorcycles, we've never had a reliable way to actually talk to each other while riding — it was always hand signals and hoping everyone caught them. With the Cardo units, we could communicate instantly if someone needed a bathroom break, and the rider up front could give the rest of us a heads-up on slowed traffic or obstacles ahead, which made the whole trip noticeably safer. As a bonus, each of us could still stream our own music through the headset, so nobody had to compromise between staying connected and enjoying the ride their own way. If you're planning any kind of group ride, this is a gear upgrade we can't recommend enough.

Devil's Tower and the Vore Buffalo Jump

Our first stop was Devil's Tower, our country's very first National Monument, designated by Teddy Roosevelt. Seeing it in person is something photos just don't capture.

Long before it carried that name, the tower held deep meaning for the Lakota, Kiowa, Cheyenne, Crow, and other Plains tribes, several of whom knew it as Bear Lodge or Mato Tipila. The tower's distinctive vertical grooves have their own story behind them. Oral traditions from several tribes describe the grooves as claw marks left by a giant bear that was chasing a group of children. As the story goes, the ground rose up beneath the children to lift them out of the bear's reach, and the claw marks the bear left behind as it tried to climb are the columns still visible on the tower today. Standing at the base and looking up at those grooves, it's easy to see how that story has been told for generations.

From there, we headed to the Vore Buffalo Jump — a fascinating piece of history most people have never heard of. Before Native American tribes had horses, hunters would stampede buffalo herds toward a hidden cliff, driving them over the edge. It let them harvest large amounts of meat and hide without the danger of hunting at close range with spears.

We wrapped up the day riding through Sundance and Spearfish before landing in Deadwood, South Dakota for the night.

Riding Iron Mountain Road and Needles Highway

Some of the best riding of the entire trip happened just south of Mount Rushmore, where Iron Mountain Road winds its way down into Custer State Park. This stretch is famous for its pigtail bridges and tunnels that frame Mount Rushmore perfectly in the distance, and it's every bit as impressive on two wheels as it looks in photos. Once we were inside the park, we picked up Needles Highway, a route known for its tight granite spires and switchbacks that make you feel like you're riding straight through a postcard. We also took the Wildlife Loop to visit our favorite Custer State Park regulars, the Begging Burros, where we got to feed and pet the babies. Dirk summed it up best: it was a day that made all of us — Chuck included — feel like true road dogs.

We did have one bit of excitement on this stretch — a bee flew up my jacket sleeve and stung me mid-ride. I pulled over, parked safely, and stripped off my jacket like a total pro (or at least that's the story I'm sticking with). All part of the adventure.

Mount Rushmore, You Gotta See It To Appreciate It

Let's just get this out of the way: Mount Rushmore is a genuinely awe-inspiring feat of human engineering, and no amount of scrolling through photos on your phone prepares you for standing at the base of it. I visited once as a kid and, frankly, wasted the moment — I was far more interested in the gift shop than four giant faces carved into a mountain. Fast forward a couple decades, add a little age and wisdom, and this second visit hit completely different. Turns out staring up at 60-foot presidential heads carved out of solid granite is a lot more impressive once you've paid a mortgage.

Naturally, we couldn't just stand there and admire it like normal tourists. We talked the kids into posing for a recreation photo. Everyone held it together — except Luna, who, in classic teenage-girl fashion, absolutely could not keep a straight face. I feel like we nailed it, and it's officially one of our favorite photos of all time.

Steam Trains, Motorcycle Museum, and a 1,500-Pound Crocodile Named "Maniac"

A few of the other highlights from this trip were ones we never saw coming. We rode a working steam locomotive on the 1880 Train from Keystone to Hill City and back, which Dirk called "pretty rad" — and he's not wrong. We also stopped by the Sturgis Motorcycle Museum the week before the annual rally took over the town, which meant we had the place mostly to ourselves. The kids were spared the obscene visuals, for now! At Reptile Gardens, home to the Guinness World Record for the largest reptile zoo, we watched a keeper get nearly mauled by 40 alligators during a show and met "Maniac," the world's third-largest crocodile — 16 feet long, over 1,500 pounds, and living in solitary confinement after eating one too many tank mates. Because no Western trip is complete without dressing up and pretending it's 1880, we also snapped some old-timey saloon photos. And somewhere in between all of it, Casper ordered and managed to finish a prime rib the size of his own head!

Nearly 1,000 Miles on Two Wheels, Countless Memories

Between towing the bikes to Wyoming and back, and the riding we did with Chuck through Wyoming and the Black Hills, we logged almost 3,000 miles round trip — with nearly 1,000 of those miles on the motorcycles themselves. However you slice it, we made memories with our kids that we know they'll carry with them for the rest of their lives.

This trip took six months of planning, a lot of trial and error, and a genuine commitment to making time for what matters most. That's the same mindset we bring to our real estate business every single day — plan hard, work hard, and always make room for what's important.

If you're local to Oklahoma and want to talk real estate, motorcycles, or your next big adventure, we'd love to connect with you.