One of the 30-mile trail's spectacular vistas. Photo by Tessa Stuart.

We’re hoofing it through a shady oak grove when suddenly—I see it as if in slow motion—my friend whips around, his face stricken like he’s just tripped the wire on an IED. “RUN!” he yells, but I can’t, because he has already practically lifted me off my feet and is pushing me back up the trail like a linebacker driving a tackling dummy across the field. We’re 50 feet away before I hear him say, “I saw it raise its tail!” Mystery solved. Matt has just seen a skunk.

(To see a slideshow of the Skyline-to-the-Sea trail, click here.)

This is not the first time Matt and I have kept an eye out for each other in the wild. We met working on our high school’s newspaper, but we might never have really known each other if we hadn’t been placed on the same 10-person crew and sent into the Big Sur backcountry for 11 days during the school’s “wilderness expedition.”

During a long stretch of day three on that first trip, I learned there is a basketball court inside the top of Disneyland’s Matterhorn, that the Monorail has the highest accident rate of any ride and that this gruff football player, always in a Navy sweatshirt, had an inordinate amount of knowledge about the home of Mickey, Goofy and the gang. If you want to get to know someone, and I mean really know someone—from his or her habits and values down to the inane trivia stored away in the mind’s recesses and how that person smells after a week without showering—an extended backcountry hiking trip is an excellent way to do that.

That’s as true for places as it is for people. You might think, for instance, that because you’ve driven on Highway 17 or 9 or 35 that you know the Santa Cruz Mountains, but behind a buffer of trees that line the road, the landscape splits open to reveal so many surprises—peaks and valleys and snakes and waterfalls, vast sandstone faces and fallen redwood giants and abandoned artifacts and, yes, skunks.

Since that first trip together, Matt (now a third-year student at Santa Clara Law School) and I have done several others—another 11 days in the Ventana Wilderness, a few weekends in the Sierras—so when my editor asked if I would hike from Silicon Valley over the Santa Cruz Mountains and down to the sea, I knew just the man to call.

Your Boss Called
This trip had started, as so many others do, with the ritual provisioning. On the way from the San Jose bus station to the grocery store, I’d told Matt I was going with a “minimalist” philosophy for this trip. He snorted, probably because he knows me well enough to take this as a disclaimer that I’d already realized at least three essentials I’d forgotten. His philosophy, he said, is “comfort”—meaning he’d be hauling a bunch of extra luxury-item weight. (Our conflicting ideologies only come to a head once, in Safeway. Me: “These tortellini will double in size!” Matt: “Let’s get two just in case. I’ll carry them.”)

There are three ways to link up with the Skyline-to-the-Sea trail in Silicon Valley: from Palo Alto, via the Los Trancos Open Space Preserve; from Cupertino, via Upper Stevens Creek County Park; and from Saratoga, via Sanborn-Skyline County Park. We’ve chosen the last because it’s possible to arrange for overnight parking here. It’s a steep 2.2-mile climb out of the valley toward Skyline Boulevard (a.k.a. Highway 35), during which San Jose and the surrounding suburbs, visible between branches, slowly recede in the distance under a thin veil of haze.

We reach Highway 35 and skirt along just below it for a mile and half before crossing at Castle Rock. I know we’ve arrived because we see the climbers, looking like hobos as they trundle up the highway with crash pads strapped to their backs. Matt’s phone beeps near the gate; we’re out of service, but he has a missed call from a partner at the law firm where he’s recently interviewed. We find a pay phone and Matt, always prepared, feeds it quarter after quarter, chatting casually as if he’s got an endless supply of them. After a few minutes he hangs up the receiver and bum rushes me with the good news: He’s just been offered his first job.

The Road More Travelled
Officially, the Skyline-to-the-Sea trail starts at Saratoga Gap, just above the northernmost tip of Castle Rock, where Highways 35 and 9 meet. The trail is 30 miles long, connecting Castle Rock and Big Basin parks and ending at Waddell Beach on Highway One. Unfortunately, it hedges along highways (9, then 236) for a third of the way, which means that once we reach it, Castle Rock’s spectacular sweeping vistas and sandstone spires are replaced by sounds and scenes a little more familiar.

There is a particular strangeness to happening upon a suggestion of civilization where it should not be. Shortly before our arrival at Waterman Gap, our camp for the night, we turn a corner to see a sky-blue station wagon that, at some point in the last 40 or so years, took a nosedive off the highway. The car has been stripped of all distinguishing features. Any insignia hinting at the make or model has been pried off, the cushions have been ripped out and replaced by a nest of branches and the steering wheel is broken in half. A little farther up the trail, bottles and jugs filled with brown liquid, along with filing cabinets and rusted-out cans of Bud, dot the hillside. I’m inclined to imagine these as hastily disposed evidence of a moonshine operation; Matt thinks they’re containers of urine.

At the campsite I look over at Matt unpacking and see that he has made sure we have extra of everything: a water purifier and iodine tablets, a pot for boiling water and a pot for cooking food, a spice kit. Just in case. I, meanwhile, realize while unpacking that I’ve forgotten a dish and utensil to eat with. The tortellini does double in size, and luckily, since the second bag turned out to be way past its expiration date. After dinner Matt sits comfortably in his camp chair reading a torts textbook. I post up on a log and make a list of the wildlife we’ve seen that day.

Skunks (2)
Snakes (4; 3 Garters, 1 Rubber Boa)
Deer (2)
Mouse (1; deceased)

And Miles to Go
The novelty of seeing pieces of civilization in the middle of the wilderness wears off early on the second day. It is three miles of asphalt and forest coated in highway soot. The terrain is not challenging, but it is trying, maybe because there is something inherently depressing about walking along a highway, being passed by motorist after motorist. Matt is not in a good mood, either; seeing two Caltrans crews standing around their trucks shooting the breeze gets him thinking about wasted tax dollars, which in turn sends him into a fit of grumpiness (“Get back to work!” he mutters under his breath). For a stretch, the highway and trail weave along the outskirts of a small enclave of homes. We walk through one woman’s front yard and she peers out at us quizzically from her living room picture window.

After three uncannily long miles, we trade Highway 35 for Opal Creek and follow the languid white waterway through several miles of elfin woodland before meeting the entrance to Big Basin Redwoods State Park headquarters. We stop for a couple of Berry Creek Falls smoothies, and the lady behind the snack bar counter says it’s another 6.7 miles to Sunset Trail Camp, where we’re planning to stay tonight. We’ve hiked 10 miles so far and it’s almost 4pm, so this is not great news. A better scenario is presented by our Sempervirens Fund map, the distance key of which suggests it is 2.75 miles. The park sign says 4.5 miles, though it cautions in big block letters “STRENUOUS.”

We bought the recommended map, a two-parter put out by the Sempervirens Fund, which built the Skyline-to-the-Sea trail and helps maintain it. Mapmakers absolve themselves of any responsibility with a fine-print note that reads: “This map is not mean to be a substitute for official maps provided by park agencies. When hiking, have current maps available and check with rangers on duty for current trail conditions.” Helpful.

In any case, we have no choice, so we start off. The trail cuts down and back up through gullies and ridges, one after the other after the other. At the start, we scoff at the warning, figuring the “strenuous” was meant to deter the less serious types (unlike ourselves), and now we are being punished for our hubris by this series of demanding elevation gains and losses that are strenuous indeed. We spend the next three hours chasing the sun. A fold of mountain will begin to get progressively darker, then we’ll summit a ridge and buy ourselves another 30 minutes of light before our trail falls into shade once more.

When we finally reach Sunset Trail Camp, the sun has just slipped beneath the horizon for the last time that day, and the chalky, madrone-shaded floor of the campground is still warm. As mid-week campers tonight, like last night, we have the whole place to ourselves, if you don’t count the swarms of mosquitoes. We set up camp, cook and devour a pot of chili while in turn being devoured by the little buggers, all before we realize that there is no water at the campsite.

“Put that in your article,” Matt says for the fourth time that day, in the same tone one would use tell another to put that in their pipe and smoke it, or to put it where the sun don’t shine. Map miles didn’t add up? “Put that in your article!” Ruthless mosquitoes? “You should put that in your article, too.” As if the powers that be—the state park district, Caltrans, Mother Nature—would read it and adjust their behavior accordingly.

The second night, hiding from mosquitoes in the tent, I take out my notebook and write: “The Skyline-to-the-Sea trail: A List of Grievances.”

Proximity to Highway
Map-Sign Mileage Disparities
Mosquitoes
No Water

The next day I’ll add “Boars?” to the list. In the middle of the night we wake up to ferocious snorting and rustling a few feet from our tent; when it’s light out we discover the Ziploc bags we’d stashed our dirty dishes in are punctured by teeth marks, 10 feet from where we’d left them. (The rest of the food is thankfully still suspended, undisturbed, in a bear bag.) A park ranger we later spoke to reckoned that we actually had raccoons, which he said can grow up to the size of small dogs out here.

“And ‘Don’t forget your bear canister!’ You gotta put that in your article too,” Matt says as we start the descent out of camp on day three.

Advice for Beginners
Coming upon it from behind, Golden Cascade, the first of three waterfalls on the trail that connects Sunset Camp with the final stretch of the Skyline-to-the-Sea trail, does not look like much. It appears to be barely more than a trickle and a murky shade almost the color of bile. By this time we should know better, though, than to have any expectations.

In a single twist of trail, suddenly spreading out before us is the kind of breathtakingly, heart-stoppingly, jaw-droppingly beautiful landscape that it is easy to forget exists outside of adventure films and children’s books. Water, imbued with a pearly white effect by the tannins leached from fallen redwoods, shimmers down the falls’ three-tiered yellow clay face. The sides of the falls, and the walls of the whole canyon, are thickly carpeted in moss and clover; ferns sprout out of every tiny crag.

The path down along the falls is steep and slippery. It edges so close to the taller, thinner Silver Falls that you can feel the spray as water slips past. We climb down through old-growth redwood forest to the final waterfall, Berry Creek Falls. It is the most arresting of all—70 free-falling feet of Santa Cruz Mountain springwater.

A couple of hours later when we exit at the trailhead across from a windy Waddell Beach, crowded as usual with windsurfers, we pass a sign that reads “Sunset Camp 6.7 miles” (so much for the 3.5 miles advised by our perennially optimistic map) and a trio of clean backpackers dropping off a pick-up car before they drive up to Saratoga Gap to start the Skyline-to-the-Sea. Do we have any advice, they ask?

Yeah—make sure to get updated maps from the park service, don’t forget mosquito repellent or a bear canister, stay on your guard for skunks, and since you’re expecting all these things, don’t expect any of them.

Reservations at campgrounds on the Skyline-to-the-Sea trail can be made up to two months in advance, and book up fast in the high season (late spring to early autumn). Campsites are $15 per night, plus an $8 reservation fee. 831.338.8861. Castle Rock State Park is on the list of state parks to be closed by July 1, 2012, but will be open all of this summer.