I knew diddly about bikepacking when I signed on for a multi-day, unsupported, ass-breaking ride on rugged Western singletrack that turned out to be a big mistake, ego-wise. Actually, the outfitter tried to talk me out of it. Please, they said, do the sensible thing and opt for our supported trip, ditch the bags and let us shuttle your gear to the campsites, bring you fresh eggs in the mornings and cold beer at night. There’s no shame in it, really. No, I said, thanks but no. I’m a man who carries his own bags. Self-reliant! A pasty city boy? Sure. In backcountry shape? Not by a long shot. A mountain biker? Well, now that you mention it, no. But a man nonetheless! Bold, brash, and autonomous! Teddy Roosevelt trekked out here, you say? Would Teddy “The Lion,” “The Bull Moose,” “The Wilderness Warrior” Roosevelt do a supported mountain biking trip? There’s your answer.
I probably should’ve listened. Minus the 40 extra pounds I carried — with bags strapped to nearly every extremity, bike and body — the going would’ve been far easier. But in a perverse way, I was glad to have done it. Rarely do I get to eject from my domestic dawdle and re-jigger my comfort zone so utterly. I’ve never been one of those types who approach the outdoors as a personal trial. But this time I sort of wanted to, and while it was tremendously humiliating (oh, frail ego!), I did it, and the rewards were huge in the end. Way, way out in the Dakota Badlands, things are prelapsarian, forsaken, and you see nary a soul. In fact, I encountered exactly one other person over three nights and four days, and 10 times as many pronghorn antelope, as I surged from pinyon-juniper forest to alpine meadow to rolling grassland and back again. Against this landscape it didn’t matter that my entire ass from tailbone to taint was insensate, or that the cornrows of spider and horsefly bites on my legs were pustuled and necrotic. I was riding too high to care.
But gear-wise, the learning curve was practically a circle. At first, I figured my messenger bag would suffice: toss in a few granola bars, Capri Suns, a bottle of Scotch; that’d get me through, right? Thankfully, the outfitter talked me into a pricey but vital set of bike bags, a hydration pack, gloves, helmet, the whole works. At pains to shed bag weight, I pared down and down again, like a chainsaw artist at the block, distilling my backcountry kit to the lightest, hardiest, biggest-league essentials. What I found was that serious bikepacking — I mean the kind that puts you where you want to be, plop in the maw of Mother Nature, far from cell towers and graded roads — requires an extensive base-level ensemble. Admittedly, altogether, it adds up. But without this stuff, or some version of it — except perhaps the inflatable pillow — you’d be screwing yourself. It’s your call, of course. What do I know? Only that each of these items was pretty much central to my emotional and at times physical survival (again, save the pillow). Central enough that I’ve piled them in a corner of my office like a shrine, where it all sits surrounded by oranges and votive candles. I bow in gratitude every morning.
Diamondback Overdrive Pro

Diamondback has a storied history of making some of the strongest, smartest, loveliest hardtail warhorses in the business, and the Overdrive Pro is up there with the burliest and baddest of all time. It’s a highly refined, exemplary piece of machinery that makes you marvel at the weird miracle of quadrilateral geometry. Designed for steep, technical trail riding, the OP has a hardy, hand-built 6061-T6 aluminum frame with a tapered head tube, 27.5-inch alloy wheels, a 36 x 22 SLX crank, Rockshox Reba 120mm fork, and Shimano 2 × 10 drivetrain and hydraulic disc brakes. In other words: exactly the hands you want to be in during high-angle, screaming descents.