Boys Weekend: Jeep Wranglers on the Rubicon Trail

Off-roading in the wilds

A.J. MuellerphotographerJason H. HarperWriter

Thursday morning, New York City.

I get an e-mail from Casey at 6:15 a.m., its tone hovering between annoyance and panic. "Dude … jumping in a cab in 10—can I at least know the airline???"

Fair enough. It's time to tip my hand and finally let the boys know where we're headed. I send out e-mails with links to boarding passes, one-ways from Boston, New York, and Chicago, all arriving in San Francisco. I grab my bag and make my own way out the door.

The four of us arrive at SFO within minutes of one another. These are my oldest and best friends: Jason Bennett, Jason Henrichs, and Casey Phoenix. The guys I love and who drive me nuts. We've bickered together, gotten stupendously drunk together, cried together, and driven our girlfriends (and, later, wives) crazy with our silliness. There is no escaping our shared experiences—they actually remember the years when I had a mullet. Two decades' worth of fun and madness and friendship.

They've got backpacks and looks of bemusement. All my secrecy may be wearing thin. "Wine tasting in Sonoma?" quips Henrichs, née Jason No. 3. (I'm Jason No. 2.) Not likely. This year is my turn to host our annual Boys Weekend trip and I've kept the location secret, telling them only that we'd be gone Thursday to Sunday and to bring sturdy boots.

It's a road trip, and two Jeep Wrangler Rubicons are in the airport parking lot, freshly scrubbed. That won't last long. My guys are off-road virgins and we're headed to rough roads indeed. Over burgers at In-N-Out, I unfurl a California map and hand each a printout. There's a photo of a Jeep atop a high boulder and the text reads:

"Bucket lists? For some, it's the Rubicon Trail, 20 miles of tears and heartbreak through the High Sierra mountains, over boulders, bigger boulders, and death-defying boulders. Only the most experienced drivers in the biggest, baddest 4x4s would even ever ATTEMPT it. Well, those guys and us. In stock Jeeps. This is about the coolest thing you can do in a vehicle, and many would give their left leg to try it. Hopefully we won't have to."

I trace our route: We'll stay at a former Gold Rush mining town tonight and hit the trail the next morning, camping out. Saturday afternoon is a short drive to Reno.

None of the guys have heard of the Rubicon, but Jason No. 1 is beaming. He loves surprises. Jason No. 3 puts on his intense "no problem" face. He grew up doing hardcore outdoorsy things, but he's spent the past 20 years in not-so-hardcore Boston.

Casey is the one who looks worried. He's the former Army captain who piloted helicopters in Kosovo and ran around Iraq in Humvees. Yet somehow he's also the one most uncomfortable with risk—hell, he's uncomfortable being uncomfortable. Forget tents: His idea of a great adventure is a casino. I promise him there will be gambling and a steak dinner at the trip's end in Reno—but only if we and the Jeep Wranglers survive.

"Goddamned Harper," he mumbles under his breath.

The trip is unfolding exactly as I'd hoped.

Friday morning, Loon Lake.

I'm looking at the custom rigs gathered at the mouth of the Rubicon, and a sliver of anxiety wriggles in my stomach. What are we getting ourselves into? Or rather, what have I got us into? The Jeeps' stock 32-inch mud-terrain tires looked massive on asphalt, but they're quaint compared to the other vehicles' supersized rubber. An idling Toyota 4Runner is jacked up higher than an Alabama swamp house on stilts. The old-timer inside sizes us up and shakes his head, apparently finding us lacking.

I've got off-road experience, but not at this level, so I enlisted the big guns: guides and trail support from Jeep Jamboree, the off-road organization that specializes in trips to the Rubicon. A TJ model Wrangler will lead us, driven by Shawn Gulling, and two pointers will follow on foot and guide using hand signals. They are Becky Mutzig and Bryan Stiles. They don't appear comforted by our citified looks either.

"Who wants to drive first?" I ask. Jason No. 1 (Bennett) takes the red four-door Rubicon Unlimited with a five-speed automatic, while Jason No. 3 pilots the two-door softtop with a six-speed manual. We turtle onto the Granite Bowl, a plain of solid rock, the trail marked with dashes of paint.

Our goal today is a mere 8 miles. We're told we should reach tonight's campsite by 3 p.m. or so. The site is owned by Jamboree and has tents, a campfire, and a cooler of cold beer. It's also the place where we can crack the bottle of good bourbon I brought along.

We hit the part of the trail called Big Sluice. The name Rubicon Trail, I decide, is a misnomer. Total bullshit.

The trail gets technical within minutes. The Jeeps are already in low gear, anti-roll bars disconnected. The pointers watch as the Jasons bumble through a boulder field. "Put your tires on top of the biggest rocks," they instruct. Clearance is already an issue. I tell Bryan I'd like to avoid body damage. "Sure," he says, but with a yeah-right shrug.

An hour later I take the wheel of the Unlimited and slowly crawl off a high ledge. Krawk! Screech, whap! Metal kissing rock. Jesus, that hurts to hear. "Who thought this was a good idea?" I ask aloud, incredulously. Jason No. 3 is walking alongside and gives me a bemused look. Oh … right.

Our Jason numbering system is derived from the order in which we became buddies with Casey. Bennett met him in an Albuquerque high school, me at the University of New Mexico, and Henrichs at West Point Military Academy. Maybe it was fate—or just laziness on Casey's part (learning new names is toilsome!)—but 22-plus years later, here we all are.

We turned 40 last year. Between us there have been five marriages, two divorces, great careers gone bad, bad careers turned great, countless parties, and many epic hangovers. We squabble ("goddamned Bennett/Henrichs/Phoenix"), but unlike our fathers' generation, we also profess our love openly. Hugs abound. They are uncles to my 2-year-old son, and we're stuck with each other til death do us part.

Still, life is busy and so are we, and we don't hang out as often as we'd like. You know the deal. So every year we escape our daily drudgeries for the annual Boys Weekend. There are three rules: 1) One of us serves as the host, and does all the planning; 2) The destination can be anyplace in the world, but it can never be repeated; 3) There has to be a surprise involved, usually something adventurous and/or harrowing. We've rappelled off mountains in Quebec and snorkeled in St. Croix, but this year I wanted something long and grueling and out of cellphone range. Besides, it's easy to talk when you're moving along at a mile an hour.

If life is a sine wave, any two of us often seem to be on the high, happy side, while the other two are riding in the lower, rougher trough. Jason No. 1, who's next to me in the passenger seat, recently broke up with a great woman who simply wasn't the right one for him. He had to move, and dating in NYC can be madness. "This was the best idea I ever had," he says, referring to Boys Weekend. "I needed this." (Screeeech. ) Indeed, the idea that we would make time for each other at least once a year, no matter what, was his. This year is our 10th.

Casey's in the smaller Jeep, making it look easy despite one wheel being totally off the ground. You can't fly a helicopter without having mechanical sympathy. These days he lives in Boston and works for a medical device company. Last year was rough, but ever the gambler, he doubled down on a major life decision and came up 21. This is his rock-star year.

Three p.m. comes and goes, yet we've only covered 5 miles. We drive over the dam at Buck Island Lake (literally over, fording the concrete barrier) and the trail gets exponentially harder. "We're never going to get through that," says Jason No. 1, repeatedly. Becky and Bryan move hundreds of rocks, making ramps, and miraculously keep us moving. "I can't believe we got through that," says Jason, right after.

Then, light falling, we hit the part of the trail called Big Sluice. The name Rubicon Trail, I decide, is a misnomer. Total bullshit. It doesn't even look like a trail, just a clog of rocks and boulders strewn into a ravine, hedged in by house-sized boulders and trees. The four-door Unlimited is too long to fit. I give up my silly idea that we'll escape without body damage. Even our phenomenal guides don't have a good route to suggest. They just shrug and let me come on down underside-banging precipices.

I recognize the smile of Jason's face. A sweet freedom, a sense of being one with a place. I haven't seen that look in years.

We limp into camp at 7:30. I pull out colorful North Face jackets I'd secretly brought for all the guys, knowing it would be mountain cold. Casey puts his on and says, surprisingly, "Dude, this is a blast. Amazing planning."

Jason No. 3 jumps into the river, washing off the trail dirt. Of the guys, he'd struggled the most, trying to find the détente between patience and power, throttle and brake. He was also responsible for the one trail tragedy of the day: He'd slammed off a high ledge, breaking our bottle of bourbon in the back of the Jeep.

"That's OK," Casey tells him consolingly, popping a brew. "We'll drink through it."

Saturday morning, Cadillac Hill.

They warned us that this section, not far from camp, would be the most difficult, and now I see why. The same jumble of ledges and boulders, but this time they are along the side of a precipice. There was a fatality here not long ago. Jason No. 3 is moving through the morass like he's born to it; suddenly he's got the rhythm. After one tricky maneuver that demanded a dose of hard gas with the grille pointed only feet from the abyss, our guide Bryan nods. "Nice job."

I recognize the smile on Jason's face. A sweet freedom, a sense of being one with a place. I haven't seen that look in years, since he and I backpacked into Wyoming's Teton Mountains in 6 feet of snow. He was in his element then, too. That was just before a good friend of his died suddenly, and life got more real, more adult, more complicated. There's something elegiac about Jason lately, a sense that he's been dragged along the bottom of the sine wave for a while. But he and his lovely wife finally left Boston this year, moving to Chicago to be nearer to their families. The rest of us can sense that good changes are on their way, the wave about to lift him back up.

Hours and many rough miles later, we hit pavement and the end of the Rubicon and we all feel a pang of regret. We say goodbye to our guides, whom we've come to respect deeply. I think we've also earned a place in their good graces. Off-road virgins, yes, but my boys listened and helped move rocks and they weren't faint of heart. In other words, they rose to the challenge just like I knew they would—even if they had no idea what they were getting into.

We blast toward Reno and cellphone coverage. The Jeeps handle 85 mph as well as they crested enormous boulders. They are amazing machines. Jason No. 3 is suddenly talking about trading in his BMW 3 Series.

In two hours we'll be showered and eating nachos and murdering margaritas, followed by a steak dinner and our annual toast, where each of us talks about each other's achievements and challenges of the previous year. This time things have been pretty good for Casey and me. Next year I'm betting some of us will have switched sides of the sine wave.

The thing I do know is there will be a Boys Weekend and it will be in a new place and on a new adventure. Friends come and go, but after 22 years, the four of us really have crossed the Rubicon together.

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