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A very old lady, slack-mouthed, frozen in thought and wearing large white designer sunglasses, goes past us. She’s driving a faded brown 1986 Honda Prelude with a miniature spare tire on the driver’s side. Her trunk is held shut by bungee cords. We’re on Highway 101 in a rented mini-van discussing our second ride of our Los Angeles weekend. We need to reccy and synthesize two notably different variations on a theme. Our speedometer reads 75mph.

Gibraltar is six and-a-half unremitting miles of improperly maintained switchbacks. It climbs, like an endless flight of stairs, from Santa Barbara to the top of a ridge and the bottom of the sky. The Santa Ynez Mountains rise 4,000ft from the back of town like a chaparral and oak studded headboard.

Ben Lieberson, a Los Angeles-based Continental rider and our ride co-host, says it’s steep, like Europe, and plenty epic. A purist, Ben likes the traditional 35-mile loop based on the climb, Gibraltar, made famous by Lance Armstrong and the US Postal/Discovery team.

Unconvinced, simply because it’s short, I conscripted LA Continental rider, Cole Maness, lover of gravel, pain, distance and the absurd, to call his best sources and manifest a slightly more demanding variation of Gibraltar.

Ira: What’s Ben’s route?

Daniel: 35 miles, it’s the way you’re supposed to do it.

Ira: And Cole’s route?

Daniel: 85 miles, with 14 miles of gravel and twice the climbing. And some water crossings. It’s definitely not the way to do it, in fact in might not even be a way to do it.

Dan: I think I need more coffee.

Santa Barbara is stuccoed, tiled and reddish brown. Vacationers wear larger than average holiday hats and short-sleeve dress shirts, colorfully suffering patterns of fish and equatorial trees. And expressive sandals. Thousands of red faces and arms fondle postcards and T-shirts. Pale legs and white sneakers rest on benches and brass animal-shaped art. Tourists engage locals and reference maps with oversized type and sea otter and surfboard icons. Ice cream is eaten and commemorative mugs are bought. Every plant and tree, regardless of size and color, looks like a variation of succulent. The town smells like fresh produce, sage and a rental beach cruiser. We find parking and set out for a bookstore and the internet.

An hour or so later, having endured the purchase of a California Atlas, several dropped calls and a tedious ‘map my ride’ session, we head up and into Los Padres National Forest with a cumbersome collection of unknown mountain roads to vet. The sacrifice required to make our 6:30am flight earlier that morning, sleep, is starting to evidence. While Ira is typical ‘on-the-road’ Ira; observant, funny, agitated and essentially entertaining and good company, Dan is broken and faded, like an incomplete teleport. Like he’s accidentally eaten pot brownies, five of them, but doesn’t know it yet. It’s 1:30pm and the temperature is well into the 90s but we’re vaguely optimistic about constructing the ultimate variation of Gibraltar.

Six hours and 85 miles later we’re six miles down a dirt road which has gone from promising to destructive to impassible in six switchbacks. Rounding yet another 180-degree turn, I recall a long conversation we had earlier that morning with the rental car woman. I can’t remember the details but the punch line was that we emphatically, if not triumphantly, declined any additional insurance. The unpaved road is rutted and covered in rocks. Ira’s neck is creased with dirt, Dan is sleeping like a derelict in the back of the van and rivulets of sweat-mud are running down the back of my knee to my socks. Option after promising option has come to nothing. Routes with beautiful views, climbs and surfaces, have proven, two, three, or on one occasion eight miles in, not to work. Closed for the season, water crossings and dead-ends have turned us around well short of finding a more epic Gibraltar.

Part 2 – Santa Barbara

At 7:00am Cole’s driveway is cool and damp and raked in early morning light. We are anxious and sunburned and ready to go. Waiting for Jeanette, friend and driver, we discuss Gibraltar. Ben, the strongest rider and climber among us, still advocates for the traditional route. Alternative rides altogether and a small out-and-back addition to Gibraltar are all considered. Stones get kicked, sneakers shuffle, and bright-red lobster arms peevishly gesticulate in my direction. Accusations are made.

Aaron: What’s your deal Daniel, the ride sounds beautiful and the climbing plenty hard. It’s the perfect follow-up to Cloudburst. Are you a masochist, or some kind of pain pervert?

Cole: Yeah, are you a pervert Daniel?

Hahn: I’m no ‘pain pervert’ but if it’s good enough for Lance to interval six or seven times in a sitting, then I’m sure it will deliver a modicum of suffering if we do it once?

Daniel: All right, it’s settled then. We’ll do Gibraltar. Plus an eight mile out-and-back that we found the other day.

Ira: He is a pain pervert but I remember that road. It’s like a scenic rollercoaster through the sky. What, don’t look at me like that, it is.

We hear gravel crunch as Jeanette’s car pops through the vegetable tunnel at the end of Cole’s driveway. Jeanette wears long, striped socks, low-top Chuck Taylor’s and a T-shirt that reads: ‘I heart backseats’. She doesn’t own a bike and works in the entertainment industry. She’s exuberant, funny and, based on a quick run down of the day and her responsibilities, oblivious to road cycling. She keeps a bona fide Mexican wrestling mask in her car. When we finally pull out, Aaron has already become a Luchador.

We’re caravanning. Three minutes and one freeway interchange into the drive, we get separated. Dan, Ira and Ben are with me in the mini-van. Our route gets us to Santa Barbara 40 minutes ahead of the wrestlers so we do some errands, tubes and food, then park the mini-van in front of the Santa Barbara Employment Office and wait. They show up.

Ira: I think we’ve timed this almost perfectly. We should be hitting the climb when the sun is highest and hottest.

Aaron: Daniel, did you even use any sunscreen yesterday?

Hahn: For the record, we stopped at a gas station and I bought SPF80, which is essentially paint. Sun Paint.

Aaron: Hey Daniel, I’m assuming you plan to ride indecently again so be sure and cover your chest, or is the hair enough?

Shoes, sunglasses, wheels and toolboxes explode onto the Employment Office stairs and sidewalk. The small, glass-and-reflections entrance becomes our locker room with flashes of red and white body parts and black and white Rapha stripes. California, immodest and jaded, hardly notices. Ira and Hahn apply several layers, thoroughly and copiously, of the SPF80. Ben’s been ready to go for the entire morning. Jeanette is smoking Camels and taking digital snapshots like a tourist at the zoo. For all the consideration given our ride, big picture, the start and first few miles through town has never been mapped. Cole and Dan discuss this.

It’s 95 degrees and 11:30am. We are standing over completely operational bikes with full water bottles and pockets full of whatever sun, music, heat and wind contingencies we think we’ll require. Cole has a ‘fun map’ of downtown so he leads.

Santa Barbara’s streets are free of trash and traffic. A cool coastal breeze chases us like a Labrador, panting and playful, up the first few hills on our way through town. The first wrong turn costs us hardly any time and climbing at all. Our second takes 30 minutes to correct and adds several hundred feet to the day. By now we’re all sweating, the heat is ridiculous and morale is at an all-time low. And that’s how we come to Gibraltar – hot, cranky and divided.

Part 3 – Gibraltar

The start feels, for several minutes, like a continuation of the approach; neighborhood streets, parks, gardens and Spanish churches. Then, with an easy uphill turn the view opens up wide and huge to the town and coastline below, and the full magnitude of the mountains ahead. There is no shade, just chaparral, grass and a now broiling wind. The sky is a bleached silver blue.

The road continues upward without traffic, sidewalks, guardrails, paint, structure or definition. The surface is broken and pieced together, like a quilt made from irregular and misshapen sections of chip seal and asphalt. The edges, sandy and covered in rocks, are barely discernible.

Ben and Ira move to the front with Hahn following quickly. Aaron has clearly checked out of the pain cave he found himself in on Cloudburst. After 30 minutes of ambitious and sustained effort, perhaps more, my bottles are empty. I’ve eaten two gels and my last banana. Waves of dizziness, panting and confusion force me to back down on the steeper sections, the hairpin turns and quicker pitches. Aaron catches me in a lull. We ride together for a pace until, on a particularly steep turn, I sink. Moving between superb legs and a world with dark edges and hot white light leaking into my head, I surge ahead and wait for Cole to pass me.

Eventually, I round a corner to find Ira on the ground in the first piece of shade since town. He looks worse than I feel. Aaron and Hahn are standing over their bikes, also in the shade.

Ira (rubbing his eyes, shaking his head, then rubbing his eyes again): This is the worst I’ve ever felt and I’m out of water.

Daniel: Is it wrong that seeing you in the dirt, looking cooked and pathetic, makes me happy? I’d get giddy but for fear of falling over prematurely.

Hahn: Where’s Cole?

Ten minutes later and still no Cole. This is odd and out of character. Hahn, feeling good and always inclined to help, mounts up and slowly rolls back down. Seconds later, Hahn comes back around the corner with Cole. Cole has a roadside bouquet of yellow and white wild flowers, expertly arranged and tucked into his shifter and brake cables. He’s been repeatedly forced off his bike by sunscreen run-off and his face is a streaked mess of SPF80, dirt and irritation. He’s still smiling and riding steadier than ever. Rejuvenated by shade, rest and the sight of Cole’s bicycle landscaping, we roll out for the second half of Gibraltar’s parched, achromatized ascent.

The second half is tighter, with more folds and less face. And faintly greener. The ocean, cold and blue, with the Channel Islands in the distance, blinks in and out of view. Jeanette and Dan catch us up in the mini-van shortly after we settle into a collective pace. Everyone but me stops to fill up on water and whatever. I continue, focused and determined. Several switchbacks later I look down to appraise the gap I’ve created. It’s big enough that I can finish alone, or at least that’s the conclusion I’m coming to when Ira passes me.

At one point near the top, in the crook of a wide, flat switchback, several cars and municipal trucks line the road. Looking under a willow tree, hundreds of yards back from the apex, a large compound of homes rises out of the dust. Screen doors, dogs, tree-swings and rust.

I see the top of the ‘Road Closed’ sign. Four more pedal strokes and it’s coaxed into full frame. I’m only a hundred yards from done, for the moment. Ben and Ira are seated just off the road, under what looks like a circular helicopter pad atop a six-foot high cement base. It’s a wide, toadstool-shaped water tank used to help contain brush fires. The top overhangs the base by several feet and underneath it’s shaded and level, an ideal respite.

I join them and wait for the others. First Hahn, then Aaron and finally Cole roll into view. They ditch their bikes and scramble up the short sandy hill to our shaded camp. We’re tired and empty and we’ve been climbing for hours. Clearly Gibraltar is concentrated epic.

Part 4 – Camino Cielo

We head south on Camino Cielo, ‘Sky Road’, across the top of a narrow ridge. Here the pavement is smooth, black and crisp, the very definition of pristine. We’ve gone from crusty grind to cool, fluid, rolling plummet. On our right, thousands of feet below, is a thin strip of town sandwiched between our mountain and an endless blue expanse white-capping west into the horizon. On our left, folds of hot-brown and sage-green mountains, rumpled and creased, continue into the heat for hundreds of miles.

At eight-miles the pavement ends at the bottom of a steep hill, just past a large gravel parking lot, home to another toadstool and the start of several enticing single-tracks. Here we turn around and leave Camino Cielo to continue south and east, inland, on a gravel fire road.

It’s 1:30pm and Africa hot. Purely on principle, turning around feels wrong. Aesthetically displeasing. I slow roll and tack back up the steep section with Aaron while Hahn fixes a flat. Ira and Ben pass us. Aaron fades as I make an honest effort at chasing. The return is longer and harder but still stunning. 30 minutes later I soft pedal past the ‘Road Closed’ sign, the top of Gibraltar, and continue along Camino Cielo in the direction of La Cumbre. It’s the highest peak in our neighborhood, at 3,995ft.

Ben and Ira are waiting in a shaded switchback. I’m suffering spells again and happy to stop. Minutes pass and there’s no sign of the others, until first Aaron, then Hahn and Cole, finish the last bit of downhill this side of La Cumbre. The road here is as busted and broken as before, worse maybe. Only the views and cool breeze make the climb over La Cumbre and the next six miles possible. On the way over, we ride into sections of green trees and dark soil. Shade and life. On the far side we pass by a shooting range littered with spent but colorful shells and backwoods flotsam and jetsam; TVs, dolls, cars and appliances. All of it shot to shit.

Eventually, the road points down for good when the already dodgy surface becomes ridiculous and obscene. Riddled with holes, cracks, and drop-offs and covered in sand, gravel and rocks. Every corner is a gamble. On cue, Aaron accelerates smoothly and confidently past the group. He floats over the worst looking sections and rails the rest, it’s like watching a magic-act. Hahn is not far behind him.

We leave the ridge on Painted Cave Road, our last descent into town. It begins easy and level, casually passing grasslands, an abandoned tennis court, some houses and a ranch. Then it drops abruptly, following a number of barely navigable switchbacks into a dark, wooded valley tucked into the top of a further ridge. The surface stays damaged and challenging until the far side of the valley. The next five miles is a series of breathtaking straight-aways, turns, angles and views. Aaron continues to lead what is now a group freefall to the Pacific.

Part 5 – La Super-Rica Taqueria

We regroup where Painted Cave meets Hwy 152, for four miles of well-paved, high-speed descent on the side of a freeway. The shoulder is sufficient. We pace line at 28, 29, then 35mph, rotating evenly and confidently into town. Spirits are high, it’s all Beach Boys and summer afternoons, high-speed cycling with great friends. It’s the end of the day and the last few miles of a long weekend.

But Foothill Blvd, the final road into to town, is longer than expected and rolls more earnestly than anyone is ready for. There’s some confusion about where La Super-Rica Taqueria, our dinner spot, actually is. Morale ebbs. The last mile through town sees in-fighting and mutiny. Low blood sugar, heat and exhaustion kick-in. Only one thing motivates me, the promise of a margarita.

At the restaurant, the line is out the door and around the corner. We take turns changing in the parking lot, between the mini-van and a PT Cruiser. Everyone seated outside watches us with pity. It must be the salt and helmet hair. The menu is all tacos. No burritos, enchiladas or chimichangas or margaritas. Just tacos and three kinds of beer. They make their corn tortillas in front of you. Conversation is random and occasionally insightful, but about what I can’t remember.

Daniel: So yeah, I think Gibraltar was enough.

Part 6 – Cue Sheet

Click cue sheet for PDF version

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