the joy of camping alone in the rain

Perched high above Woodstock, New York, suspended like a perpetual wave on the cusp of crashing under the weight of its overhang, looms Overlook Mountain. The peak itself is rather unremarkable, hardly higher than 3,000 feet; more noteworthy are the sights one passes on the featureless gravel path that trudges upwards. After parking next to a flag-billowing Buddhist temple, one ascends relentlessly until the hollowed skeleton of a burned-down 19th-century hotel rises suddenly from the mist. From there, it's a quick ten minutes to the summit and the fire tower that always seems one misplaced step from collapse. The rattlesnakes that like to sun themselves on the peak make themselves known in this section of the climb - usefully, one is typically so winded by the final stretch that heaving lungs keep eyes fixed downwards. It is not a long hike but it is brutal and monotonous; there are no flat sections, only loose, vertical scree that perpetually assaults, in equal measure, one's will and one's ankles.

Overlook means many things to many people. For the middle-aged firefighter alongside whom I used to volunteer at the local food pantry (please don't interrupt my virtue signaling), it is a site of ritual and fitness - he goes up and down every morning, lest he ever be out of breath when called upon to supply the jaws of life. Contrast that with the brilliant Four Tet, a Woodstock local for whom Overlook clearly offers something both meditative and transgressive, a place where the natural and the digital worlds can converge subtly and abruptly. There are senior citizens who use the mountain as a glorified stairmaster, daytrippers up from the city eager to feel immersed in the woods before re-immersing in Brooklyn by sunset, and bizarrely, a shocking number of European tourists who I imagine are lost, surprised that the 1969 festival was held at such elevation. For me, well, Overlook carries many meanings.

I have written before about what a place can mean - but I have not written about what a place can come to mean. There is a distinction there, as fractional as it might seem. For years, Overlook existed in the Gerson familial shorthand as a stand-in for anything arduous, anything to be derided - 'I'd rather hike Overlook' went the refrain whenever presented with, say, an invitation to a New Jersey bar mitzvah. Its metamorphosis into a site that verges mightily close to the spiritual is not only a recent personal development, but a conscious, intentional one. What compels a shift like that? And what factor - tangible or not - delivers that shift the gift of permanence?

The evolution began early in the pandemic, roughly a month after returning home to Woodstock. It had taken shockingly little time for misery of a peculiar form to install itself: mundanity plummetting into deteriorative monotony at a pace so accelerated it felt malicious. Anyone reading is familiar with the feeling, the nauseous haziness of those first weeks. In an effort to either reassert control, arrest the rapid atrophy of every useful muscle in my body, or simply exit the house - likely a combination of all of the above - my mom and I began climbing Overlook at sunrise. It was one of the few acts that felt genuinely danger-free - masks were abandoned, hand sanitizer forgotten, six-foot distances easily kept from chittering chipmunks and owls. And it was nice to be together, just us two.

We did it a few times, frosty exhales adorning April and May mornings. Then summer arrived and the sun rose too prohibitively early to continue. For a while, after I moved back to Washington D.C., Overlook faded from memory. But a year or so later, at the advent of a potent quarter-life crisis, I returned to Woodstock, only to find that the grip the mountain held was stronger than ever.

Two nights ago, on Friday, I climbed Overlook alone, a too-heavy pack strapped to my shoulders. I had begun camping at a secluded, semi-secret spot on the summit - always by myself - in the summer of 2021 but this would be my first night spent up there in the rain, as well as my first vernal sojourn. Everyone I passed was mid-descent and clad in multiple waterproof layers; people looked at me strangely, a woman paused to ask if I was training for a race. It is an abnormal act, a brazen act, to arrogantly plod upwards when the forecast warns of high winds and thunderstorms. The night before, after I had shared my waterlogged plan with my Brooklyn roommate, she had stared me down with a truly withering look of pity before solemnly shaking her head and muttering, mournfully, "that's the whitest shit I've ever heard."

Overlook is an eight-minute drive from my house and if I'm in good shape (an infrequent occurrence), a forty-minute sprint to the top, close enough for dinner cooked before departure to still steam at the summit. That proximity is not meaningless - it delivers the sensation of being plunged into wilderness while mitigating most of the actual dangers of being in the wilderness.

Such convenience permits a rationalization of the discomfort inherent to a night spent camping in the rain with insufficient gear (nothing can go that wrong if you're only an hour from your bed, the flawed logic asserts), and it's that discomfort that delivers Overlook its newfound meaning, as contrived and flimsy as it might be. During COVID, when so much suffering was externally imposed, there was something liberating (and fundamentally privileged, of course) about choosing when and how to impose it on yourself. While the pandemic might have faded, suffering will always endure, and so too does the curious mirth that accompanies willfully wading into its warm waters.

Everyone has manufactured discomfort in their own ways over the past several years. People busied themselves with the unbelievably rote displeasure of regularly baking sourdough, others taught themselves languages or musical instruments that they immediately abandoned, and many of us remained in jobs that mistreated or overworked us, lest we surrender to the feeling of surrender. Much of that self-inflicted discomfort was performed by the subconscious - who in their right mind wanted to add another log to an already blazing bonfire of anguish?

But now, as we half-heartedly return to whatever we have designated as 'normal,' many have realized that there is joy and freedom to be exploited from sinking into the uncomfortable. People are doing more drugs, moving into vans, abandoning careers, and asserting themselves more forcefully in personal and professional relationships. Conversations are more honest, harsh advice is dispensed with less reluctance. And some of us are camping in the freezing rain.

I reached the top around 7:30, twenty-odd minutes before the sunset that I knew would be obscured by cloud cover. My priority was setting up my tent before the downpour commenced (inclined towards discomfort as I might be, sleeping in a wet tent is where I draw my red line). And so I worked, fingers moving with methodical efficiency. Stakes plunged into soft soil, poles extended and connected and all of a sudden, miraculously, a structure stood before me. I threw my shit inside, made sure the rain cover was well-fastened, and then the downpour began.

It was a thoroughly miserable evening. Being the idiot that I am, I had cooked squid for dinner and to the shock of no one, my stomach hurt. Forty degrees feels much colder than it looks written down and my sleeping bag, a half-decade removed from being capable of zipping closed, was losing heat quicker than a corpse. And as beautiful as my campsite might have been, it was likely the most exposed spot on the whole mountain - winds carried in from Massachusetts and Connecticut harassed me all evening, waking me, sneering at me, scaring me. When I rose at 5:45 to catch any sunrise that might have filtered through the haze and was greeted instead by a mist that limited visibility to fifty feet, I couldn't help but laugh.

The laughter didn't stop - which was strange because, for a moment there, I could have been in real trouble. As I stowed my gear, the wind and rain stung my exposed fingers with a ferocity that forced me to constantly pause mid-task to plunge my hands into armpit or between legs until feeling returned. Thirty seconds on, two minutes off. This routine is funny only until it very much isn't and still, the laughter came. My cotton sweatpants grew heavy and clingy, my shoes squelched and slipped, and the grin on my face stretched wider. Maneuvering my unfeeling arms around a dripping tent, flailing and failing to return it to its sleeve, I remembered a trip up Overlook in January 2021, the only time I had ever hiked it in winter.

A group of hungover friends and I had attempted the climb, naively, without crampons, our feet glissading recklessly over the icy path. Arriving at the summit long after the sun had risen, we slid back down on our butts, wet and very much not in control. We had all laughed that morning, laughed harder than we maybe ever had before, but now, with my fingers spasming in my groin, I wondered if I had been the only one who had actually enjoyed himself. Doesn't matter, I told myself. Discomfort, like a place that holds meaning, is always personal.

Back in my car, feeling flooded into my extremities - and so did the anxieties all too familiar to contemporary life. Less conspicuous than their return was how palpably absent they had been up on the mountain, even in the moments that demanded anxiety. It was a jarring realization that as I had teetered on the edge of genuine risk (to my wonderful grandparents: don't worry, I'm exaggerating all of this), my blood stubbornly refusing to circulate, I had felt less encumbered than at any previous moment over the past year.

Alone in a tent on top of a mountain - or outside of it, while you stuff uncooperative nylon haphazardly into your pack - as the freezing rain arrives from all directions, there is no distraction, no immediate escape. There is only yourself and discomfort, and all the warmth it brings.