I’m still trying to figure out what I just did, and why. It wasn’t until I had already walked a mile from home and halfway across the Brooklyn Bridge that I ever considered the reality of this walk: almost 120 miles, from my house to my best friend’s house upstate… And yet already on the bridge I start to feel twinges in my knees and a little ache in my foot. I had planned to walk over 30 miles today, and each day until Tuesday, but I had no idea if I could even do it.

This is not your regular hiker’s trip; I’m not even much of a hiker. No, this was intended to be a Gentleman’s Journey, just to see what it was like to walk some distance through our mostly civilized world, to escape the bubble of the city under my own power, for a change. I have no Gore-Tex™ or CamelPack™ or Trekking Poles. I’m wearing black jeans with a shirt and vest and tie, a wool sweater, a scarf. I have some good boots. The compass my sister Annie gave me for Christmas is on a Victorian hair chain in my vest pocket. I brought little else but a change of shirt, socks and underwear, and a notebook, a flask of whiskey and water. It all fit neatly in a small red backpack. It couldn’t have helped that I was only running on about 4 hours of sleep, after the same number of cocktails at Hotel Del Mano the night before. For many reasons, I’m sure I’m a sight…

I feel like a freak even still in the city, walking with purpose but still unsure what that purpose is. Stopping at the Union Square farmer’s market makes the day seem like almost any other. There, I buy my usual pile of apples (well, a smaller pile anyway) and a little bag of pretzels, plus some organic muffin to eat on the way. It’s still quite cold for Spring, so I get a hot cider and stand in the sun for a while, watching the morning shoppers and tourists. I stop again just a dozen blocks away at the Ace hotel to use the bathroom and adjust my backpack, which is already chafing. This isn’t progress; these are all places I already know.

I am not in any clearer mindset from walking either, maybe more crazy than usual. Well before 14th Street I have already obsessed over (in alphabetical order) Art, Basketball Hoops, Boston, Blue Jeans, Dance Parties, Musical Notation, Point-and-Shoot Cameras, Sex, Video Games, and Why I Hate “Street Art”*. I am weirdly nervous about this stupid adventure. I mean, I know it’s ridiculous to think about, but what if I died…?

At least the day is warming and the sky a calming blue. In Times Square I see a beautiful woman who had stopped in a ray of light to raise her head to the sun, eyes closed, face glowing. I want to take a picture, but I can’t budge… and then she sees me and moves on. A hundred blocks later, as the city rolls uphill, I see a handsome young man with his face aimed at the same sun. I have a sudden urge to reach my giant arms through space and time, and to turn the heads of the beautiful sun-lovers toward each other, as they should be.

At 170th Street I am marching to the George Washington Bridge. A guy politely asks me if I’ll help him get something to eat. We’re near a Gyro Truck so I tell him to order whatever he wants… I’m thinking about a time my mother did the same thing for a woman outside a Burger King in Boston when I was a teenager, and how much it impressed me. Over the years I’ve had to learn a lot about the nature of Help. One must choose (or not choose) to help without judgement, I think. If you can give, just give without question. However it is human nature (and also neuroscience and evolution and so on…) to make quick judgements about another person. Here is a nice man – with shoes and clothes certainly in better shape than mine at the moment – asking for help. I do wonder why exactly, but let it go. I figure, if a man is going to ask another man to buy him a sandwich, I’m gonna buy him a goddamn sandwich.

Soon I’m on the George Washington Bridge and it’s kinda scary – long, windy and fast with traffic. I’ll be getting onto the Long Path from its beginning in Fort Lee Park, and hoping to take it almost all the way to my friends’ house in West Nyack. The Long Path is a pretty well-maintained walking path that goes all the way up towards Albany, mostly through woods and parkland. Aqua-colored blazes painted on trees and posts mark the way to go. It’s more level than the Shore Path that goes right along the Hudson, and has me trekking through the trees between the Palisades Parkway and the river. Sometimes I’m way too close to the ugly highway, but sometimes the views across the cliffs to New York are spectacular. So much of it is rocky and muddy, though, and much harder going than I expected. This is not a Gentleman’s Walk anymore. It’s hiking.

I’m in the woods for a long time, trying to enjoy Nature (when I get far enough away from the cars.) I have to stop often, though, and I’m not relaxed or zen-like at all. It has taken me all day to let the busy thoughts go, but at this point I have not found any real peace, even when the woods are quiet. Instead my brain is preoccupied with my body. Simple endurance consumes my thoughts, as does the constant cataloguing of aches and twinges. Can I make it? The first Panic sets in – if I stop and sit for more than five minutes I have a hard time walking for the pain. Soon I start to worry about the time, too. This stretch on the Long Path turns out to be a lot longer than I realized, and has added a good 7 miles to an already long day.

Since I’m losing light I decide to step out of the woods and follow the straight road toward Nyack. This, unfortunately, puts me soon onto Route 9W for a few miles, which seems more dangerous than I expected, especially in the growing dusk. After a while walking uncomfortably here, I notice the Long Path blazes have joined me on the road, and when they veer back off into the woods, I follow. I’d rather be caught in the dark among the trees and coyotes than I would be on the road, wearing black and trudging wearily against the traffic…

The path meanders through Tallman Mountain Park for a while, and suddenly – maybe for the first time all day – I’m in absolute heaven. The sun shoots low through the still bare trees, making the leaf-covered ground shimmer in gold and picking out the dead ghost-white leaves leftover from winter. They tremble wickedly in the wind – the only things that do – like the spirits of condemned men hanged en masse. I take a bunch of snapshots and look around in wonder. I see only squirrels, and a few geese that fly by overhead. It’s quiet as hell. I am totally exhausted, but I am happy.

This last hour through the park is physically brutal, though. I can barely walk at this point, after ten hours without much of a break, and I have to climb the stone steps up the hill at the end. I rest at the top and drink some water, wondering how in the hell I can walk another few hours to reach Nyack. All I can aim for right now is to reach Piermont, on the other side of the hill, and rework my plan there. However, the little descent lacks even the structure and stability of the way up. The stairs are just a jumble of angular broken stones, and I picture myself pitching down head first to the bottom at each step. Finally at the bottom, all I can do is hobble a few hundred yards around the corner to the Irish Pub at the edge of town. I just keep walking at a steady pace right on into the bar, pull up a stool, and order a scotch. I am done.

I don’t really know what to do now, since I’ve walked 32 miles and apparently still have another 6 or so to go, and it’s getting late. I don’t particularly want to walk the dark highway, but the parks will be closed at dusk, which includes my last chunk of the Long Path… I mean that’s if I could move. My legs are about to mutiny and eject themselves onto the bar floor.

For the first time all day, I turn on my phone. My friends Tim & Kara had gone to a baby shower in Manhattan today, but have made it home by now, and are about to eat dinner. Kara sweetly insists on coming to get me in Piermont, and I’m not inclined to argue now. I don’t have two hours of walking in me, even if I wanted to… I guess it’s ok to suffer this small defeat. (And O how de feet do suffer!) Instead I’m soon much happier in the bosom of the family, playing games by the fire with their daughter Ray, and eating delicious stew and salad while the Marrieds tease each other cutely. I stretch I shower I sleep. Maybe I should just stay here for the weekend and go home.