Overlanding is about the journey, not the destination — but it’s hard to enjoy the journey when you’re elbow-deep in a duffel bag at dusk, searching for the headlamp you swore was right on top. Out on Vermont’s Class IV roads, where the weather can swing from sun to sleet in an afternoon and your campsite is your basecamp for days at a time, a little organization goes a long way. Giving every piece of kit a designated home means faster camp setup, quicker teardown, and smoother meals — which leaves you more time for the things that actually matter: a laugh around the fire, a longer look at the map, one more ridge before dark.

There’s a practical side, too. Every rig has a finite amount of storage, and knowing exactly what you packed (and where it lives) helps you balance weight, protect your gear, and keep your vehicle handling the way it should when the road gets rough. In this post, we’ll walk through simple, field-tested ways to categorize, store, and reach your gear so you can roll into The Pilgrimage — or any weekend on the trail — ready for whatever the mountains throw at you.

Staying Organized: Personal Items

For most of us, organization starts with what’s on our body. Keys, wallet, and phone live in zipped pockets so they don’t go wandering the moment the trail gets bumpy. A small sling, fanny pack, or chest pouch earns its keep fast once you start carrying the little essentials: a headlamp, sunscreen, lip balm, a multi-tool, a snack, and the bandana you’ll use ten different ways.

Top Tip: Store everyday-carry items in clothing you won’t take off, like pants pockets rather than a jacket. Layers come on and off all day as you move in and out of the vehicle and the temperature shifts — and that’s exactly how a phone ends up lost in a footwell.

If you’re rolling with friends or family, the goal is for everyone to keep their own gear contained. It doesn’t take long for loose stuff to migrate across a cab, especially on washboard. A visor clip, a few carabiners, and a dedicated pouch for small tools (knives, a GPS messenger, a flashlight) keep the important things findable. A shared “common” bin is worth its weight, too — stock it with snacks, hand sanitizer, a paper map, and trash bags so the whole group knows where to reach.

And don’t forget the humble toiletry bag. A hanging Dopp kit keeps your toiletries together and off the ground at camp, which matters more than you’d think when your “bathroom counter” is the tailgate.

Staying Organized: Clothing

Vermont in the fall is a master class in changing conditions — warm afternoons, frosty mornings, and the very real possibility of rain or mud at any point. Space in the rig is limited and the weather isn’t, so smart clothing storage makes a genuine difference in how comfortable your weekend feels. A few habits that help:

Choose Your Bag Wisely

After the backpack, the duffel is the overlander’s best friend. A rugged, waterproof duffel can ride on a roof rack or sit outside at camp without soaking through, and because it has no hard sides, you can wedge it into the odd gaps every vehicle has. Look for one with exterior pockets so wet socks or muddy footwear don’t end up against your dry layers.

For boots and shoes, a hard-sided bin or case is hard to beat. It keeps muddy hiking boots contained and protected — and keeps the inside of your rig from smelling like four days of trail by Sunday.

Use Packing Cubes and Compression Sacks

Packing cubes and compression sacks tame the chaos and reclaim space you didn’t know you had. Everyone organizes a little differently: some split by type (base layers, mid-layers, sleepwear), others by day, and others by activity — your rain gear in one cube, your camp-evening warm stuff in another. If your cubes aren’t see-through, a quick color code saves you from opening all of them to find one fleece.

Roll, Don’t Fold

Rolling clothes instead of folding cuts down on wrinkles and, more importantly, lets you stuff garments into the small corners of your storage. It works beautifully for t-shirts, base layers, and pants. Bulkier items like a heavy fleece or insulated jacket are often better folded or kept loose where you can grab them fast.

Keep a Dirty-Clothes Bag

Give worn and wet clothing its own home — a large mesh bag is ideal because it breathes and lets damp gear dry out instead of mildewing. Toss in a couple of clothespins and a length of paracord and you’ve got a clothesline for the inevitable rained-on socks.

Favor Multi-Use Pieces

When space is tight, every item should pull double duty. A puffy jacket becomes a pillow. Quick-dry base layers work for hiking, sleeping, and lounging. A buff is a headband, neck gaiter, dust mask, and ear-warmer depending on the hour. Pack for versatility and you’ll carry less while staying ready for more.

Top Tip: Pack so you rarely have to move one thing to get to another. The gear you’ll reach for most — rain shell, headlamp, snacks — belongs on top and within arm’s reach.

Staying Organized: Electronics

In a perfect world we’d all leave the screens at home. In the real one, most of us travel with at least a phone, and plenty of us bring cameras, drones, a GPS unit, or a laptop for that Monday-morning return to reality. More devices mean more cords, chargers, and small parts to lose — so they deserve a system of their own.

Build a “Tech Essentials” Kit

Keep your electronics and their accessories together in one padded bag or hard case: phone, camera, power bank, GPS, chargers, spare batteries, SD cards, and adapters all in one place. A case with internal pockets or pouches keeps the little stuff from rattling around, and a hard shell protects fragile gear from the dust and jolts that come standard on Class IV roads.

Tame the Cables

Charging cords multiply and tangle faster than anything else you carry. A simple cable system fixes it: bundle cords with Velcro straps or twist ties, and stash them in a zippered organizer with labeled slots. If you’re traveling as a group, a quick label or color code keeps everyone’s cords — and chargers — straight. Adhesive clips on the dash or console give frequently-used cables a fixed home so they’re not snaking across the cab.

A Word on Weight and Recovery Gear

One Vermont-specific note: organization isn’t just about convenience, it’s about safety. Keep your recovery gear — traction boards, a kinetic strap, shackles, a small shovel — together, accessible, and secured so it isn’t buried under three duffels when you actually need it. And anything heavy should ride low and centered, not stacked high, to keep your rig stable on off-camber sections and stream crossings. A tidy load is a predictable load.

Conclusion

The Pilgrimage is about moving through the landscape with intention — and that intention starts before you ever air down. A thoughtful organization system saves you time, energy, and frustration on the trail, and it frees you up for the part of overlanding that actually drew you here: the people, the quiet, the next forgotten road. So give every piece of kit a home, pack it where you can find it, and roll into Vermont ready to go a little further. See you on the trail.