EDITOR’S NOTE: This is an ongoing series about setting out to hike 32 miles around the island of Manhattan in a rainstorm and the thousand-mile road that led there.
“I went out for a walk, and finally concluded to stay out till sundown, for going out, I found, was really going in.”
—John Muir
I was at a Men’s Wearhouse, of all places, when I was first confronted with the idea that I wouldn’t finish the Great Saunter.
To that point, my, at times, delusional and unbridled confidence, which has buoyed me through life — for better and worse — hadn’t even allowed me to consider that I wouldn’t complete this incredible, preposterous 32-mile hike around the island of Manhattan. It had been some six weeks since I’d stumbled into Inquiring Minds and subsequently resolved to take part in the event, and the thought of not succeeding hadn’t even crossed my mind.
We were getting fitted for tuxedoes for the wedding and I was telling all the other groomsmen — and, really, everyone I crossed paths with in my life at that point — about this absurdly cool, delightfully bold event that I was about to undertake.
That’s when the best man, an exceedingly smart person, said something to the effect of, “Let me know if you do complete that.”
It was a noteworthy and concerning reaction because it was delivered without the slightest hint of malice. He didn’t want me to fail. Rather failure was just the logical conclusion. A recovering, or, more accurately, recovered lawyer, he was the individual who had warned me about the misery of studying for the LSAT and the horror of law school that follows. Something about how the LSAT will “fry your brain” is the phrase that stood out.
I, of course, didn’t take his advice. To add an extra degree of difficulty, I’d gone on to sustain the first of my two concussions — this one courtesy of a bicycling accident — on the eve of my first practice test.
It could not have been a more perfect evening. I rode across the Golden Gate Bridge and back again, and had almost returned to my old Cow Hollow apartment when I detoured to my favorite grove of trees, on the edge of the beach at Crissy Field.
All of a sudden, my head hit the ground with such force that my AirPods popped out. I’d taken the turn onto the gravel path too sharply, and before I knew what had happened, I was sprawled out on my back. I tried to pull myself up, but, dazed, fell back down. It wasn’t until hours later that I realized I’d cracked my helmet.
Studying for the LSAT while recovering from a traumatic brain injury (and working full-time from home during a burgeoning pandemic) is as insoluble a mixture as one can concoct, it turns out. I did, three months later, after a hazy summer of studying, take the test. I scored satisfactorily enough to get into one, solitary school, who also extended me a significant scholarship.
One of the books I read in the months before my trip was Jon Krakauer’s Into Thin Air, a true tragedy in the sense that the reader knows disaster awaits from the very outset of the expedition. This was doubly true for me because I remember originally reading the book shortly after it was published in 1997. I would have been 9 at the time. I’m not sure how I managed because on my second read — after nearly a decade of working in jobs where my chief professional responsibility was to write — there were still plenty of words I had to look up.
Attempting to climb Mount Everest is an incredibly reckless thing to do. Krauker, in his own way, admits as much. So, too, is attempting to walk around Manhattan, in its own little way.
At some point before the storm swoops in, the adventure writer details the competing schools of thought on high-altitude training. To simplify things, mountain guides disagree on how much time climbers should spend above a certain altitude. The exact elevation — whether it’s 26,000 or 28,000 — is not terribly important. Especially when you stop to consider how outrageously high those altitudes are. That’s more than ten times the height of Mt. Tamalpais, and two-and-a-half, almost three times taller, than the famed ski peaks encircling Lake Tahoe.
Once you reach a certain altitude, the oxygen-deprived atmosphere wreaks such havoc on the human body that any benefits accrued through acclimatization are undone by the general chaos of spending any time at such heights.
In the weeks and days before I took off for Florida, it occurred to me that my training regiment might have left me woefully underprepared for what was to come. This feeling was only magnified as the Shorewalkers’ Instagram account began to share Stories from Great Saunter veterans completing marathonish-length hikes.
The area beyond 26,000 feet on Mount Everest is, alarmingly, known as the death zone. I followed the logic of the mountain guides who have their clients largely eschew training on that part of the hill.
Sure, I, too, should have completed a 20-something mile training walk. In fact, originally, I’d planned to do just that. I would start off around 10 miles and then add on a couple of extra miles on each successive hike.
Instead, in the run-up to the Great Saunter, I never made it past 14. In any other context, that would be a damn good hike. But it wasn’t even half of what I was supposed to do on that Saturday in New York.
I told myself that an 18 or 20 mile hike — like spending time north of 26,000 feet on Everest — was just as likely to provoke an annoying injury as it was to prepare me for the 32 miles to come. As long as I had a reasonably high level of recreational fitness and an unflappable desire to get this done, to keep putting one foot in front of the other, I’d be fine.
All my hikes and trail runs into Marin — and beyond — notwithstanding, the first official training walk, which I memorialized on Strava (that became de rigueur for all that followed), came on March 24.
It only seemed fitting that, in the spirit of Shorewalkers, I should hug the shores of San Francisco. So, I decided I’d walk north from my apartment into Fort Mason — my favorite, or, at least, one of my favorite city parks — then continue along the coast past Aquatic Park, Fisherman’s Wharf and the entirety of the Embarcadero until I made it to Oracle Park, the waterfront home of the San Francisco Giants where I’d spent hundreds of nights in the most beautiful press box in sports, typing away at my MacBook, drinking coffee until 10pm and never once missing a print deadline. During the summer of 2016, I’d covered 78 home games, which is an insane thing to do. Especially considering that I was also covering games across the Bay at the Coliseum, the cavernous concrete bowl where I’d grown up watching the Oakland A’s, and mixing in coverage of the Golden State Warriors, and offseason happenings of the then Oakland Raiders and San Francisco 49ers.
“Delightful,” was the first descriptor I’d used in the brief post-walk notes I’d jotted down. In my backpack I had a book I wouldn’t read and an empty water bottle. I figured I could fill it up along the way.
After about five thrilling miles, I thought to myself, “Huh, this is pretty long.”
I ended up walking 10.6 miles in an unintended loop. I didn’t know exactly what to expect. I figured the walk to Oracle Park would be about six miles, but it was hard to be sure because Apple Maps takes you the logical way, not all along the water on the scenic route and along impromptu detours, like when I spied 163 Main St., a luxury high-rise that corkscrews 400 feet into the sky. I ended up turning around just shy of Chase Center, the home of the Warriors, who less than two months later, would appear in their sixth NBA Finals and win their fourth title in the past eight years. I’d covered the first five all in Oakland at the erstwhile Oracle Arena.
I headed north back through the city, but before making it home, I stopped at Roam to order one of their characteristically elaborate and ostentatious burgers and the onion zucchini haystack, the latter of which I cannot recommend enough.
All through the day I marveled. There’s an unrelenting joy in the simplicity of walking right out your front door and into an adventure.
That was certainly true of walk No. 2 when I again put on my Hokas, stepped right out of my front door and headed toward the Golden Gate.
I was walking to Sausalito.
I made it more than 12 miles. And, thanks to the bus, I was back in the city in about 12 minutes.
Sausalito boasts a picturesque waterfront with an abundance of houseboats, harbors and marinas, and no shortage of spectacular, if overpriced, restaurants that trap tourists just arrived from San Francisco at the nearby ferry terminal. The town, perched on a hill, cuts a distinctly Mediterranean profile, with houses crawling further and further up the slope before giving way to the Marin Headlands and Mt. Tamalpais beyond that.
To arrive in Sausalito, I walked along the beach and under a long, narrow pier, climbed up into the Presidio, ducked into an old military tunnel along the East Battery Trail, and stopped at the Round House Cafe, which has the best view of any coffeeshop in the world. Built in 1938, the Art Deco-style cafe, is, as the name would suggest, perfectly round, with enormous windows that look out on the Golden Gate. I continued across the bridge and into Marin.
After completing my 12 miles — which included accidentally trespassing onto a private beach — I realized I had time to stop at a deli before catching the bus back to the city. As I stood on the street, devouring a turkey club sandwich, a tourist asked me where I’d got it. All I could manage was, “500 feet,” and a point because I was too busy eating and too hungry to stop.

The next training walk — a quick 5.5-mile out and back to Crissy Field, the very place where I’d toppled off my bike — was memorable mostly for what I found waiting for me in my mailbox when I returned home.
Shorewalkers had sent me a small manilla envelope containing a bib — I was No. 1339 — and an impressively detailed and annotated two-sided map that, as I examined it, left me to wonder, “What exactly have I gotten myself into?”
It was the middle of April, less than two weeks before I’d be heading off to the wedding, and this little saunter had bothered my feet far more than it should. Then there was the consideration that I was still in physical therapy for my left ankle, which I’d felt crack on the Dipsea Trail way back at the end of January.
My longest training walk, the aforementioned 14-miler — 14.1, per Strava, to be exact — came one week before I flew off to the East Coast. Allison had a work event to attend, so, I was down in Mountain View, one of those Silicon Valley hubs. Unfamiliar terrain. After spending far too long hemming and hawing on AllTrails, trying to find the perfect hike — even considering driving up to Pacifica to climb Montara Mountain, a hike I’d long wanted to complete, but which made no sense in the current context (I wanted a trail that was flat and urbanish; Montara was rugged and stood more than 1,900 feet tall) — I realized that the answer was right in front of me all along:
Stevens Creek Trail
Stevens Creek begins on the west flank of Black Mountain in the Santa Cruz Mountains, meandering through Stevens Canyon, and the cities of Cupertino, Los Altos, Sunnyvale and Mountain View before finally spilling into the San Francisco Bay. The creek is named for Elijah Stephens, one of the early settlers of Cupertino, who led the first successful wagon train across the Sierra Nevada in 1844. The expedition began with 50 members and ended with 52, as two babies were born along the way. The only explanation for the Stephens/Stevens confusion is that someone made a typo somewhere along the way and it’s never been fixed.
On that Wednesday, the creek, which guides the trail, was largely dried up but the walk was surprisingly scenic.
I walked along the suburban forest that springs from the creek bed, past two buildings that looked like giant spaceships, then along the trails into the marshes that gradually gave way to the Bay. I walked past an old, apparently abandoned NASA lot with a ruined sail boat, a seemingly shot-up and bombed-out shuttle bus, and an airplane. Later, while trying to take a shortcut to lunch, I stumbled onto the Ames Research Center, a NASA base at Moffett Federal Airfield, where the parking lots are all filled with an absurdly large fleet of hummers and other transit vehicles — all painted tan. I wondered how long they’d just been sitting around, collecting dust.
One of the factors motivating me to hike around Mountain View was the fact that doing so would lead me to a free lunch. I slipped onto the satellite campus of a tech giant that shall not be named where my co-conspirator, who, shall also not be named, provided me with a delicious lox sandwich, which was really just a lox bagel with a poetic license. I made it back to the Sleeper Avenue Trail Entrance where I’d left my car having walked 14.1 miles.
My legs felt great the next day, an encouraging sign. But I had a headache, almost like I was hungover. Oddly, my sweet new hiking socks, which I’d acquired via Amazon, at a dear cost, had given me blisters.