This article was first published in Issue 138 of Rouleur
I have always had a soft spot for the framed photos in family-owned restaurants across the western United States. The worn sepia snapshots of the establishment when first built, the black and white lithographs of idyllic days fishing on the lake, the questionable authenticity of the signatures on post-coloured prints of spaghetti western film stars... all hung above the counter in bars and on walls around the fireplace couches at hunting lodges, and in such density that they cloak the wallpaper patterns behind the booths at old diners.
Those photos have always made a place, no matter how out of the way, feel like a home. Over decades, I’ve stepped into these locales on cycling trips countless times, sometimes in lycra but most often just après ride, face gaunt and quads aching, in Carhartts and Birkenstocks. The bartenders and waitresses of the USA aren’t yet as accustomed to cycling kit as those of the Alps, always seemingly serving my light beer or bacon and eggs with more respect for the traveller than the tourist. It’s a peculiarity I’ve long chalked up to America’s mystique and appreciation for long-distance driving, at the core of which sit roads.
That term – roads – is one I’ve grappled with for nearly as many cyclical seasons as I’ve been spinning cadence along them. By definition, a road is simply a path for expedient travel over a landscape. Not a place in and of itself, but rather a link between places. Webster’s does few favours for cycling, instead our salvation is found in the words of America’s travel and nature writers. While William Least Heat-Moon has perhaps never been six hours into a Grand Tour stage parcours, the parallels of life’s experience are enough that he could once write, “A road is a beckoning, a strangeness, a place where a man can lose himself.”

There is an irony that roads afford an opportunity to lose oneself, when more than 80 per cent of mainland America itself lies within a kilometre of a road, an endlessly metastasising grid, established for conquest as much as connection. Maps of the United States: the Rand McNallys, the American Automobile Association Atlas, and those published by the government itself in the form of United States Geological Survey quadrangles, display varying aspects of our roadway system depending on the assumed purpose of the reader. By and large that purpose is driving, usually for long distances between towns or cities. As such, these maps forego a fair number of smaller streets and roads, and typically only label major points of interest.
Between the nearly 6.75 million kilometres of roads in the USA, only 322,000 are free-ways or highways – major roads often four lanes wide designed for expedient vehicular travel. That leaves 6.43 million additional kilometres of streets, avenues, routes, and boulevards, most of which simply aren’t worth the time to kit up to ride. But it is the blank spots on these maps, the negative space often shaded in pine green hues, that hide the bounty of the largest road manager on earth – the United States Forest Service – which manages 600,000 kilometres of roadway, largely for the purpose of logging and recreational access.
It was exactly those extensive paths on public lands that led me to the place I call home: Ojai, California. Fifty kilometres inland from Santa Barbara, where the Pacific Ocean washes up against the North American continent, Ojai is a small town of 7,000 residents tucked within a valley against the flanks of the mountains that make up the Los Padres National Forest. For a town often marked on roadway maps as a nameless black speck amid pastel green, it belies its quiet nature, having been a stop on two editions of the Tour of California (TOC) and as the winter getaway for Hollywood’s stars and movie productions (Lost Horizon 1937, Easy A 2010, Smokey and the Bandit 1977 etc). While the Amgen TOC leveraged the rolling foothills along the southern aspect of the valley, it was the expanse of taller peaks to the north that drew me in. Only one road veers north from town, Highway 33, rising over 1,500 vertical metres along a 50km meandering paved surface that follows the Sespe Creek from its confluence with the Ventura River to the summit pass where its headwaters form.

The 33 bisects this section of the Los Padres National Forest, cartographically splitting apart wilderness areas, geologic terranes, and ecological tones with a two-lane wide strip of asphalt. Along this road there are two primary branches, each to the east. The first, Rose Valley Road, follows a perpendicular valley filled with towering cliffs of sandstone, reminiscent of whales breaching from a chaparral sea. These formations are remnants of ancient sand bars within a shallow ocean from more than 130 million years ago, but today rise over 1,000 metres above sea level, waterfalls pouring over their edges, mountain goats sitting by hot springs at their bases.
The second of these roadway deviations occurs at the summit saddle of Highway 33 itself, splitting off onto Pine Mountain Ridge Road: a single lane path of cracked concrete climbing an additional 800 metres skyward to a true summit at Reyes Peak. It was the 33 and its two tributary roads that offered me all the riding my heart could ever desire: 60 kilometres of pavement harbouring disparate climbs of 1,000, 1,500 and 2,500 metres, as well as a network of trails stretching in every direction from these primary roadways. In all, well over 150 kilometres of rideable surface stretched out from just beyond my back door, offering world-class road climbs, mountain bike descents and panoramic views. I thought I loved Ojai for its temperate climate and access to recreation, but finding the feeling of it being a true home didn’t occur until an unintended visit to the local diner.

While it had never been quite intentional, my visits to diners had always been reserved for road trips. Quintessentially American, diners (akin to the British transport café or French bistro) were designed and patented in 1893 to be casual-atmosphere restaurants composed of booths and a bar counter, serving a wide array of simple meals across extended hours, often 24/7, with the intention of serving travelling customers. The modest nature and popularity of early diners led to their establishment across America, in large part thanks to the railroad system, from which entrepreneurs took both patrons and literal train cars, which they built their diners from.
It was this local character that often led to décor being determined by whatever the owner had on hand, which more often than not, happened to be photographs and memorabilia of purely local significance. For all these reasons, the diner three blocks down the street, serving an eclectic menu of meatloaf, tacos, dark coffee and hamburgers, wasn’t on my list of local restaurants to experience. It was only after a ride up the 33 that included an unplanned addition out Rose Valley Road that I came to realise it was the only establishment open after 9pm on a weekday in this little town. And so I found myself in a corner booth, having stopped by the house just long enough to switch out of riding kit, SL8 Roubaix leaned up against the wrought iron fence outside, where I could watch it through windows old enough to be made of thick paned, distorting glass that accentuated the variation in tube diameters.

I couldn’t for the life of me recall what I had ordered, only that it was undoubtedly both unremarkable and somehow contained more calories than I needed in that post-ride moment. What did stick with me were the framed photographs plastered across the walls. Above my head was a photo of a Model T Ford driving through a small rock tunnel. In triptych on either side was an image of a mid-20th-century truck driving past distinct geology with 10-foot snow-banks arching overhead as well as a candid portrait of a man walking a mule laden with saddlebags down a steep, rocky trail. I got up and wandered the near-empty diner to other booths, looking at old postcards from medicinal hot springs, photographs of sailboats in an alpine lake and trophy trout, and trifold brochures for deer hunting.
Each was a view into the past of a place, the proprietor kind enough to make a small note tacked underneath, noting the location on Highway 33 where it was taken. Over the course of one short meal, Highway 33 had ceased to be a literal road, a bridge of expedient travel between two locations; instead it became a place in and of itself, more closely resembling the definition of a trail – a trace that acts as a physical representation of the relationship between humans and place.

And a trail it truly was. In the furthest corner of the diner, where the long bar met the wall, an old map hung in a cheap frame. Through the cracking plastic protecting the long-worn parchment, a clear solid line of road could be drawn up the existing delineation of the 33 until it stopped only 10km up canyon. Beyond that point in Wheeler Gorge, the location of that initial single-lane rock tunnel, dashed lines ran upslope, denoting trails instead of roads connecting over the mountains towards the Central Valley beyond. Underneath the asphalt and bitumen of Highway 33, Rose Valley and Pine Mountain Ridge Road lay the footprints, wagon tracks, rail lines, homesteads and stories of those who lived in a place long before a road ran through it. A ride up 2,500 vertical metres over 65 kilometres along the conveyance of Highway 33 to the summit of Reyes Peak had become more than a covering of distance, more than the longest road climb in California, instead it had become a covering of time, a chance to sink deeper into landscape with each metre ascended.
Over years, I sought stories of the 33 and the Topa Topa Mountains that surrounded it. Books from the early 20th century filled with stories of homesteaders, grizzly bears and Basque sheep-herders scraping a living out of jagged peaks and valleys. Oral stories of Chumash (Indigenous) histories scattered around the landscape, revealing original place names and relationships established thousands of years prior to European contact. Torn and faded maps, some old enough to have been measured by metes (French for distance) and bounds (direction), a technique largely dependent on natural features of the landscape being used as references for measurement and boundaries, acted as a stochastic flipbook, revealing additions, amendments, and disappearances of trails, roads and settlements among folded hills.

Old photographs and postcards suggested shifts in cultural values just as much as they provided reference to phenomena instantaneous or imperceptible – wildfires, landslides, the gradual loss of fish in the river, the sedimentation of an alpine lake behind a dam… Collected into a small library to be framed and hung or folded and stored in a shed already full of hanging bikes, these disparate stories of place had come together into a contiguous tale linked together only by sinuous connection along Highway 33. Like the ruins of an ancient church, this infrequently travelled road had become a half-forgotten artefact that revealed cultural values between its cracks, reminders of who we are and who we were. Riding it had become more of a pilgrimage than a workout. A chance to transform the pride of riding the longest contiguous road climb in California into reverence for the historical figures on whose shoulders this road rests.
The wind gently weaves between palm fronds, coaxing salt-laden humid air from the shore-break of the Pacific Ocean up into the foothills at the very base of transverse mountains that lead up to Reyes Peak. At Highway 33’s terminus at the edge of the North American Continent, a soft adobe wall crumbles into tall golden grasses, remnants of the Spanish Buena Ventura Mission and its aqueduct built by enslaved Native Americans in the waning years of the 1700s. Spinning northwards the asphalt changes character, from cobbled concrete into smooth bitumen, a covering-up of train tracks that once connected Ojai to the coast until the early 1900s, an early breakdown of American public transit.
The first gas station en route is adorned with a mural of American country music star Johnny Cash, who lived locally and managed to ignite a 500-acre wildfire with his square-body truck in the 1960s. The road narrows and car traffic dissipates as the highway bisects Ojai, passing pixie orange groves with only mountains and the oil fields of California’s central valley in the distance. The concrete of Matilija Dam towers overhead, its basin silted up after several decades as a geoengineered alpine lake, offering a fraction of the water it once did to the confluence with the Ventura River at its base. Piercing cliffs of limestone through tunnels long since shifted in number and size on account of public safety, a natural spring letting out from mountainside marks the entrance to Wheeler Springs, once the terminus of the 33, known for its hot springs and post office that held the title of ‘smallest in the nation’.

Tacking to and fro up roadway laid in the 1930s, akin to a sailboat against stiff wind, switchbacking out of dense chaparral into hanging valleys filled with sycamore lined creeks and airy pine and fir, there is little ahead or above but further crests of mountains as broken and steep as crashing storm waves. Breaking over the last steep pitch of the initial 30-odd kilometres, the climbing eases at the intersection with Rose Valley Road, marked more clearly by a single towering Bigcone Douglas Fir than by the bullet-ridden USFS sign tucked behind fire-scarred chaparral. It is here that the landscape delineates its own intersection, colloquially known as Puerto Suelo – a Spanish derivation describing a pass separating river drainage. This shift in mountain repose divorces the roadway from the Matilija drainage into the Sespe River Valley. It is here that the roadway shifts between geologic substrates, from cream coloured sandstone to dark gray shales bounded by red beds, brought into direct contact and muddled into a mélange through millions of years of faulting.
It is this geology that determined the direction of trails, and later roads, in this upper basin, travellers having long selected the path of least resistance to the highest peaks above. Hardy yet unfoolish, the Civilian Conservation Corps (CCC) division of the 1930s simply laid roadbed directly on top of these old trails, turning what was footpath and wagon track into the 33. This blurring of the line between what differentiates a trail from a road is only more starkly distinguished by the historic CCC camp surrounded by pine trees lying across the road from the falling-away foundation of an even more historic cabin that housed ranchers a half century prior to the great depression.
As the road continues its whirling contours upslope, a handful of additional homesteads are passed, each holding onto countless stories of poets, cattlemen, trappers, shootouts and miners past. At the summit saddle of the 33 at 1,600 metres above sea level, a road cut exposes arches of colourful warped sandstone, bent over in a complete chevron, a pastel rainbow arching from the Pacific Ocean down into the badlands of the Cuyama Valley beyond. It was down in this valley that 35,000 people gathered for a barbecue in 1933 to celebrate the completion of the highway, originally named Maricopa Road. Instead of descending into this high plains desert with its vineyards, olive groves and endless sagebrush scrub, a right turn is taken up Pine Mountain Road, or 6N06 as it is denoted on the U.S. Forest Service map.

Climbing due east, this single-lane road struggles to maintain the crest of the ridgeline, the asphalt surface increasingly pockmarked by potholes created from falling boulders and extensive snowpack. Along the road, large sandstone boulders and pinyon pines become progressively denser, their forms distorted by constant winds. Several campsites and trails appear alongside this glorified carriage path, modern reflections of the locations of natural springs and ore deposits that once tempted humans to eke out a life this high up in the mountains.
Deep depressions have been worn into the largest of boulders through their use as mortar bowls, echoing the tens of thousands of years that the Indigenous Chumash people harvested pine nuts and held reverence in this place so largely erased from the atlas. One final gasp of broken cobbles leads into a final kilometre of well graded dirt, at the terminus of which lies a rocky outcrop overlooking hundreds of thousands of acres of largely unbuilt landscape. It was here that the road was built in the 1950s by Standard Oil in order to access the site of a prospective oil well that never produced a drop. A fire tower once stood on stilts three storeys overhead, but burned down as many have, in ironic twists of fate, never to be rebuilt.
Laying the bike down at 2,500 metres’ elevation, all sense of self has been drained by countless pedal strokes searching for resilience against gravity, each simplifying life’s complexities into nothing but relationship to this landscape. Descending this narrow roadbed, speed and drained muscles blur the contrast of ecologies, road, trail and self. Historic context acting as a key to decoding what cycling has always meant for me, a way to decipher the palimpsest surface of roads, understanding the layers underneath. An understanding of landscapes as storied, with roads acting as repositories, becoming more than just bridges from point A to B, instead the oldest of paths contour landscapes, surrendering to place and past just as much as a rudderless boat amid strong seas.

Pointing the bike south on the 33, the computer quickly ticks up to 50 km/h, the landscape’s colours increasingly become smudged by speed, the chatter calms as the bike planes and my mind has little to consider but past, place and leaning into the next turn. Native people long crossed this pass on foot, soles beating paths into sandstone and oak leaves. Wagon tracks crossed these mountains in the 1860s, hitching the interior west to ‘place’. The first cars crept through in 1933, and in the near century since, storms have washed away roadbed, forest fires have melted asphalt and rockfall has blocked tunnels. Landscapes, and least of all roadways, are never quiet, but their language is one that must be learned through veneration and observation. Turning the definition of a road more closely into that of a trail is accomplished just as much off the bike as it is over the course of turning cranks along its course.
Rolling into town just over five hours after the ride’s start, little feels more appropriate than to coast between the wrought iron gates of the diner down the street from my house. No one seated at the bar cares that I’ve ridden my bike more uninterrupted vertical metres than possible anywhere else in California, but there is a twinkle in the eye of the waitress when she sets down a margarita, seeming to recognise my weather-worn kit as that of a traveller, no different than the sweat-stained hat of a long-haul trucker.
The bicycle and a road had offered a connection to place typically reserved for families with generational ties, aided only by a few time-worn photographs that instilled a deference for the grandiose shoulders I stand upon each time I head out for a pedal. As cyclical as the seasons, each ride offers a chance to eschew going solely further, choosing instead to etch deeper with every pass. This is how roads become storied landscapes, holding the history of generations past in onion-like layers lain into the earth.