When Boondocking Dreams Meet Montana Reality

It’s easy to boondock. There’s an app and about a billion places you can pull off the side of the road to sleep. The hard part is finding a spot that actually makes you pause—the kind that reminds you why you boondock in the first place. Somewhere not too close to other people, open enough for Starlink to work, near a trail you can hit before dark, and not miles out of the way from wherever you’re headed next.

Our goal has never just been to “be off grid” or pat ourselves on the back for not sleeping in a house. I love camping, but not more than I love a flushing toilet and a hot shower. What really pushed us to trade the comforts of a house was the chance to see the most beautiful corners of the country. Which is how we ended up changing our Montana itinerary three times.

The plan started with a night in Butte. Then we swapped it for Missoula. Neither panned out. We couldn’t find anything that checked all the boxes—until we stumbled on a spot south of Flathead Lake. As soon as we saw it, we knew it was “the one.”

We rolled in around dusk, the kind of light that makes everything feel a little more dramatic. The road was empty. No cars. No people. Just us, the rolling hills, and the eerie awareness that we were deep in grizzly country. Google says there are only about 12 bear attacks in North America each year, but it sure feels like your odds go up when you’re sleeping in the woods full-time.

When our Garmin finally announced we had “arrived,” we were greeted by a little firepit tucked under towering trees. It was perfect. But then we spotted a small road just to the left. Naturally, we had to see where it went.

Around the bend, there she was—a clearing that stretched wide open, with mountain views that seemed to go on forever. It instantly made our top five campsites of all time. And as if that wasn’t enough, the next morning we woke up to a sea of clouds spilling across the valley, with mountain peaks poking through like islands. Pure magic.

The next night, our plan was another epic site, a handful of spots tucked along a river not far from Whitefish. Too good to be true. And sure enough, it was full. We should’ve suspected as much, being so close to town, the national park, and right on the water.

We regrouped quickly and aimed for a place that looked promising: a quiet site tucked between rock faces with its own little beach. The closer we got, the worse it felt. We crossed multiple train tracks, got tailed by a truck for a few miles, and passed a handful of abandoned houses. By the time we neared our destination, our gut told us if this spot was still available, there was probably a reason. So we turned around.

Now it was late, and we had an early morning ahead. We checked a few more options, but they were either crowded, covered in trees (bye-bye internet), or came with a fee we didn’t feel like paying. We were tired. Which is how we ended up at Whitefish Resort.

The office was closed, but a security guard assured us we could just park for the night and sort it out in the morning. Not exactly the “wow” spot we’d been chasing—and yes, it came with a price tag—but it also came with the gift of getting to go to bed and the bonus of “bike in, bike out” access to the lifts the next day. 

We closed out the week with a final stop at Lake Koocanusa. This time, we scored big. A wide-open stretch of shoreline that felt like it belonged entirely to us. The water was glassy, the sky wide open, and the whole lake stretched out in front of us. 

Sometimes you win. Sometimes you don’t. But the hunt is half the story.

Watch our week in Montana!

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Jackson Hole, New Friends, and Revisiting Old Dreams on the Road