Black Bear Road is a 10-mile can of worms, cresting nigh 13,000 feet above Telluride. For some, it’s a Jeeper’s nightmare. For others, it’s on the bucket list of adrenaline-spurting destinations. For the architects of Hell Week, it’s a soft warm-up.

The very idea of a ride called “Hell Week” is all a sane rider need know to take a pass on this trip.

Our leaders, Mick Williamson and Jason Houle, are well known among the hard-core adventure riding community. Some might say they are notorious. Most of us have ridden with these men before, yet here we are.

Crashing is an integral part of Hell Week.

I struggle up The Chute, over baby heads and through ruts worn by decades of spinning Jeep tires and eons of snow melt. My BMW R 1200 GS Adventure seems to know the way, so I let it run free. My friends are watching… the pressure is on. The exit is a solid rock stairstep — steep, wet and unforgiving. I have come this far without a single dab. I’ve got this. There’s my line… but I miss it by a tire width. The front wheel jerks skyward. My performance ends with a flying leap to safety.

The tough Wolfman luggage takes the brunt of the fall so the bike is fine. Instinctively, that's an adventure rider’s first concern. I land wobbly on my feet like a crippled cat, just managing to stay upright as I leave the scene in shame. Before I can get back to my bike, Mick and Jason have already picked it up. They will repeat this process for most of us time and time again over the next several days. They arrange this carnage, but they also ensure that everyone who comes on these rides gets the help they need to get home again.

Brown Mountain, heading for Corkscrew Gulch.

Rock slides have closed lower Black Bear and we are forced to retreat to Imogene Pass, an alternate route to Telluride. After a brief lunch stop in Ouray, we can’t resist a side trip to Yankee Boy Basin before heading over the pass. A steady rain keeps the dust at bay. At the trailhead, a head count discloses Doug’s absence. Before we can return to look for him, a Jeeper drives up and says one of our crew has fallen. We rush down to find Doug’s GSA lying on its side and him sitting addled in the trail. We fear a concussion, and his leg might be broken. Mick and Jason shuttle man and machine the nine miles down to Ouray, then return for Mick’s GS. Thankfully, Doug has shaken off the circling sparrows and his leg is only bruised. He insists he is well enough to ride home… back to California.

The rain increases as our remaining eight riders tackle Imogene Pass. Most of us wear Klim gear and so far the Gore-Tex is keeping us reasonably dry.

Atop Imogene Pass.

Imogene begins near the Camp Bird mine, winding over irregular bedrock and through aspen and pine forests before giving way to high mountain tundra above timberline. Loose scree commands our concentration as we ascend the marginally maintained roadway. I stop momentarily to ensure the others are keeping up, then ease out the clutch to continue. My rear wheel spins without warning and I lose my balance on the off-camber terrain. The fall snaps my right hand guard, leaving my brake lever exposed to the inevitable next tumble. We climb to the 13,114-foot summit, then descend to the abandoned Tomboy mine above Telluride, where I fashion a makeshift hand guard from a 100-year-old scrap of mine timber.

Dragoo's makeshift hand guard repair.

Unblunted sun at high altitude. We overnight in Telluride, then take the picturesque Ophir Pass to connect with Corkscrew Gulch to the east, across Highway 550. Corkscrew leads us to the dreaded Poughkeepsie Gulch.

Above Lake Como, a dozer operator takes issue with our presence. He expresses his disdain by parking his blade across the narrow path, forcing some of us to take a steep alternate route. There are no signs waving us off and this county road is open to traffic so we presume he doesn’t like motorcycles and ride on.

Five flats and at least two bent rims. Otherwise, it wouldn't be called "Hell Week."

Jeepers know Poughkeepsie as a metal bender... a place where armor, lift, and locked differentials are advisable. Marked anchors indicate where to attach the winch cable. Thankfully, we are going down, but signs that say, “Winch Point” do little to suggest this will be an easy descent.

Kyle questions his line as Jason prepares for the worst. Jason goes first without hesitation, expertly picking a thin line down a crack in the rock. Mick chooses a different route, which costs him a windshield in the subsequent forward endo. With a little help spotting my entry, I manage to ride down okay, but poor Kyle wipes out his F 800 and breaks a finger. Chris, Tyler, Jason Apelquist, and Darryl get down the ledge by various means and we are finally on our way… to the rock garden.

Kyle shakes off the crash as the pain sets in on his broken finger.

This stretch is essentially a river of boulders from baby heads to beach balls, only less forgiving. Some riders pick their way down, taking a few falls but finally arriving at the Uncompahgre River at the edge of the timberline. It is exhausting work. Less patient, I barge through the wet rock like an icebreaker in the North Sea. The big GSA is formidable when bashing through loose stones and most move just enough to allow progress, as long as momentum is maintained.

Today is Day Two. We have five more to go. It is shaping up to be “a hell of a week.”