Lessons Learned in My “Rookie Season” of Overlanding

The final days of spring are approaching, and the last patches of snow and ice are melting off the higher elevations in the Pacific Northwest. Locals have begun the annual ritual of swapping out their ski boxes and snowboard racks for the rooftop tent, and the rising temperatures can only mean one thing – it’s about to be prime-time for overlanding! If the overland bug has bitten you in the recent past, or if like me, you find yourself fairly new to the scene, stick around. I’m about to download three critical insights I gained during my first year in this space, and it’s because of those insights that I can’t wait to get back out on the trails.

Now I am well aware that some of you have likely been exploring nature in your vehicles since before I was born. If that’s you, hopefully we can agree that there’s always more to learn. Perhaps you’ll find that some of my lessons can become your own. Take from them what you will – I’m happy to share!

For those of you dipping your toe in the water, considering building your own project or modifying your existing daily driver, I’m so glad you’re here.  I was you a little over one year ago, with the exception that I think I either got pushed in or dove in head first—I honestly don’t remember which is more accurate. The good news is that I’m happy either way, and with the tips that follow, I hope you can say the same a year from today.

Overlanding Tip #1: Distance From Civilization is not Directly Proportional to Cool Factor
When you are first getting started with overlanding, making the jump from spending your travel nights at a Best Western to making camp at the top of a Jeep Badge of Honor trail may be a lot to ask, both for you and for your vehicle. Fortunately, the bar doesn’t need to be set so high, so don’t. One of my earliest discoveries as I got out onto the trails is that I didn’t have to drive into the middle of nowhere just to escape civilization. Reality is, you may not need to be more than a mile or two off the interstate for the right terrain to make your overnight camp site feel like you’ve escaped the modern era.

One of the great things about overlanding is that it IS about the journey. Having your bed with you at all times changes how your schedule is arranged.  You don’t have to make it to a hotel in a certain city – you just set up camp where and when you want.  This frees you to explore those little gems you’d otherwise fly by trying to stay on schedule – to literally stop and smell the roses, if you will.  With a new, more relaxed attitude and agenda now realized, I just kept my eyes open, because there are some incredible things you can discover right off the side of the road!

Creative Upcycling – The Pickup Retaining Wall
Through much of 2024, I lived in Missoula while attending the University of Montana. Every time I make the trip from Missoula to Boise to visit my parents, a unique man-made landmark signifies to me that I am halfway to my destination, regardless of which way I am traveling. It’s not some insane feat of human engineering, nor is it a 14,000-foot tall snow-capped mountain. It’s simply a line of trucks from the thirties to the fifties that has been used to make a retaining wall at the edge of a gentleman’s property. Stopping to marvel and consider the stories these old trucks could tell, I decided to pull out my camera and shoot a few photos. As I walked the line of trucks, now seemingly being held captive by the protective thorns of wild blackberry vines, I looked back over my shoulder and realized I was at the perfect angle to look across a footbridge that spanned the river below. The point is this – by taking the time to slow down and explore what was right in front of me, I gained a new perspective and experiences I’d have otherwise missed out on. While I don’t recommend sleeping there, If you’re ever driving the route through Lolo pass from Boise to Missoula, keep your eyes peeled for the trucks!

Was The Lion King Filmed in Utah?
Another significant “slow down and enjoy it” moment happened in May of 2024, returning from my first-ever Overland Expo in Arizona. My father and I were several hours into our 860-mile return drive from Flagstaff to Boise, slicing through the middle of Utah. There were a million beautiful spots along the way that would have made for some great photos, and some we stopped and messed around at, but none piqued my interest more than one that sat a mere ten seconds off the side of the highway. The surrounding cliffs were deep red, and the way this one rock poked out, you couldn’t help but picture Rafiki holding Simba up over the edge.

Giving into my childish desires, I pulled off the road, and seeing tire tracks up the spine, flipped around and drove straight up onto this rock as far forward as my dad, now spotting me, felt was prudent. With my car now perched on this commanding pedestal, I pulled out my camera and slid my way down to the highway for some photos. Now this in itself would have been cool enough but not 30 seconds later a very well-outfitted Tacoma, also returning home from Overland Expo, saw where I was aiming my camera while driving past me, flipped around exactly like I had, and asked if he could drive his rig up right behind mine! He then jumped out of it with a camera in his hand, and came down to introduce himself. In the 10-15 minutes that followed, not only did we both get some pretty awesome shots from the road, but I made a new friend (with common interests) out of the experience, which brings me to lesson number two.

Overlanding Tip #2: Travel in a Herd. More Friends = More Fun, More Spots, and More Memories
While this may seem like a no-brainer, saying ‘the more the merrier’ could never be more accurate than when it comes to overlanding. Sure, have your own rig. I like being able to sprawl in my tent! But past that, there are countless reasons why camping and traveling with friends makes the whole experience better. Plus, making your early trips with a few other possibly more-seasoned overlanders can accelerate learning the ropes without all the bumps and bruises, so to speak.

Traveling between the NW Overland Rally and Overland Expo PNW in July of 2024, I struck up a conversation at a gas station with what looked like a small caravan of like-minded travelers. I was pleased to find out they too were headed for Redmond, Oregon, so we hung out for a couple days at that event. The Overland Expo events (five now across the U.S.), and similar expos, gatherings, and rallies that happen all over the country year-round, are incredible opportunities to network with both overland brands and enthusiasts. You can meet others that may have the same vehicle as you, ask people how they like a certain upgrade you’ve maybe been considering, and most importantly, make new friends.

While attending events like these may seem intimidating at first glance, just remember that everyone started at zero, and many of them still remember what that was like! In the camping areas you will find everything from a simple cooler, blanket, and air mattress in the back of an otherwise stock SUV, to inspiring, fully built-out custom rigs and expedition vehicles, all with owners that love to talk. Point being, there is something for everyone. Oh, and here’s a total side note: there are dogs EVERYWHERE. By simply talking and spending time getting to know my new friends at this event, I got invited to join them at a quick campout spot they were going to hit immediately after.

By this point in my overlanding experience, I had solo camped a few times on my way to and from some Washington events, and around my hometown of Boise, but Oregon was uncharted territory for my rig and I. As such, I had no clue where we might be heading. Fortunately, my newfound companions had a location in mind only a few hours away. We set out from Redmond, Oregon towards Mt. Hood, where we would be spending the next few nights.

The more people you KNOW, the more spots you’ll GO
The beauty of going out with a group of people is that there are good odds at least one of them has been to wherever you are going before. I followed a caravan of two Tacomas, a Ford Ranger, and a Lexus GX through the mountain roads until we reached our turnoff. So you may be wondering if the drive up at this point was rough and even a little intimidating for a first timer like myself. Absolutely! But they knew where we were headed and what we were getting into. Plus, knowing we had multiple vehicles for recovery concerns, and watching a bone-stock Ranger take on everything in front of me was all the reassurance I needed to push my Cayenne forward up the trail. In the end, not only did I get more confidence in my rig and my capabilities, but the destination and the days that followed were more than worth every bit of stress I may have experienced during the climb. The memories of that trip still stick with me today, but there’s one memory specifically that is of utmost importance. I remember all the things I didn’t use because I didn’t need them.

Overlanding Tip #3 – Enter Slowly and Learn From Others
If there is one thing anyone in the overlanding space will tell you, it’s the reality that overlanding is not an all-or-nothing endeavor.  You can do a lot with a little, and everyone may have their favorite piece of equipment, but you don’t need them all, so don’t buy them all.

When you are first getting started, think about what means the most to you.  Do you want to have cold food storage without worrying about ice? Get a 12v cooler!  Do you want to sleep off the ground and be able to never make your bed? Get a rooftop tent!  If neither of these concerns even entered your mind, spend that money on something else. Go ahead and rock the Igloo cooler, and keep your sleeping bag in the back of your rig! The bottom line is that you need to determine what you want your priorities to be, or you can go broke on equipment really fast!

And while we’re talking about equipment costs, here’s another big tip – borrow first and buy used! This is another place where that larger circle of friends can come in handy – many of them may have gear they’d let you try out—maybe even on an actual weekend outing!

Finally, once you’ve narrowed down what you want, look for used gear, either online or at thrift or resale stores. I can’t tell you how much of my gear isn’t new, but merely new-to-me. I borrowed my first rooftop tent from a neighbor, then bought it from him at a discount—four trips later. My Dometic fridge was ½ price (and like new) on Facebook Marketplace because the original owner used it once and wanted a bigger one. My RIGd tire carrier cost me a 30-minute drive and a couple of Benjamin Franklins from a guy who sold his 4Runner and got a pickup. Over those three items alone, I saved over $2,500 by buying used, and I’ve never had an issue with any of them.

LET’S GET ROLLING!
That’s enough reflection already. After all, another overlanding season is before us with trails waiting to be explored. With these tips in your back pocket, I hope you found something to take with you on your next adventure, and if it happens to be anywhere in my neck of the woods, look me up. You’ll find me on Instagram, here in the pages of TREAD magazine, or somewhere out on the road doing what I love and making new friends along the way.

@dillon.houck