The Trip You Keep Not Taking

Four years ago, one person had an idea. Sturgis. Motorcycles. A house up in the Black Hills where a group of us could actually cook dinner together instead of eating separately every night on the road.

What none of us knew at the time was how close it came to not happening. Not because of weather or money or timing. Because of the person who dreamed it up in the first place.

I booked the house myself, a place in Lead, South Dakota, up at a ski resort. That detail mattered more than I realized going in. Having a home base instead of a string of hotel rooms meant we actually got to know each other. Dinners together every night. Sitting around after a full day of riding, comparing notes on the road, laughing about the camper we watched try to turn around on Iron Mountain Road after realizing there was no way it was fitting through the tunnel ahead.

It wasn't until we were in the middle of the trip that people started talking. Small things had been happening, little moments of friction that felt off, and it turned out more than one person had almost backed out before we ever left home. Nobody had said anything to each other beforehand. They just quietly wondered if this was a mistake, and then went anyway.

I won't get into the specifics of what went wrong or who caused it. That's not the part of this story that matters. What matters is that a group of people who almost didn't go, because of doubts they never said out loud, ended up having the trip that made them a group in the first place. We still travel together today. Four years later.

The riding itself is the part I'd tell anyone about first. Iron Mountain Road is unlike anything I'd done on a bike, curve after curve, cutting straight through mountains, tunnels carved right into the rock that frame Mount Rushmore perfectly if you time it right. Parts of the Black Hills looked like something out of Batuu, those same otherworldly rock formations, like you'd ridden onto a movie set. 

We spent a day in Custer State Park watching buffalo wander across the road like they owned it, which, fairly, they do. Rolling hills, golden grass, the kind of weather you don't get to plan for and just get lucky with. A park ranger rode up on horseback at one point and stopped to explain how the park works and what his day actually looks like, mostly keeping the buffalo safe from people who get a little too confident with their camera phones.

We got lucky too. A friend of a friend, a German guy who makes the trip out every single year, gave us an unofficial tour one day and knew exactly how to route around the worst of the Sturgis crowds.

He got us views of Mount Rushmore from angles most people never see, without ever paying to park and walk into the main viewing area. As newbies, we would have leaned on GPS and probably missed half of what we saw that day. Instead we fit in more sights in a single day than I would have thought possible. That's the kind of thing you can't plan for and can't buy. You just have to be open to it when it shows up.

My son came on this trip too, on a Sportster he'd bought the year before. He'd had his motorcycle license for maybe two weeks before we left.

Watching him keep pace through Iron Mountain Road's curves and the mountain roads around Custer, both the German rider and our friend of a friend kept commenting on how well he handled himself for someone so new to riding. I'd be lying if I said that wasn't one of my favorite parts of the whole trip. A proud mom moment on top of everything else.

Not every day was easy. The ride out to Devil's Tower in Wyoming might be the hardest riding day I've ever had. No shade. No trees. Heat like standing too close to an oven, and even the wind off the bike at speed didn't cool anything down, it just felt like being breathed on. I was drained in a way that had nothing to do with the miles.

But that's the thing about the trip you almost don't take. The hard parts end up being part of what you remember, right alongside Iron Mountain Road and the buffalo and the dinners in that house in Lead. None of it would have happened if everyone who quietly considered backing out had actually done it.

There are a couple of stories from that week I'll keep just for the group, the kind of inside jokes that get brought up every single time we're together, four years later. Every group of friends who travels together has a few of those. This trip is where ours started.

One of them turned into a running joke that still shows up every time we rent a house together. We make sure every bedroom door has a lock, ever since somebody got a little turned around in the middle of the night in an unfamiliar house that wasn't their own. We joke that one of these trips we're finally going to buy glow sticks so whoever it is can find their way to the bathroom and back without incident.

That's the thing about a trip like this. It doesn't end when you get home. We just got back from a weekend up in Maine, three couples, just over 500 miles round trip, two nights celebrating America's 250th together. Our next big trip that isn't on two wheels is a cruise to Alaska. None of it happens without that first Sturgis trip nearly falling apart before it started.

I think about that a lot when people tell me they're still deciding whether to go on the trip they've been circling for years. The ones who almost didn't go are usually the ones who end up telling the story the most.

If there's a trip you keep almost booking and then talking yourself out of, I'd love to help you actually take it.