Portals: Cycling From NYC to Boston

Friday Afternoon

A sliver of a river slides beneath the rails and then we’re in Queens, floating over a great plain of brick row houses and tessellating backyards, little boxes of space framed by high fences. I love the train for its glimpses at unseen places: rooftops covered in broken glass, a hidden tag from some intrepid graffitist, a favourite lawn chair left on a nook with a view. In one backyard, a yellow-haired girl stands on the bricks and stares at us.

Behind me is the racket of a kid’s tablet game, but the sight of Manhattan crowding the western horizon has seized a pair of middle-aged women beside him.

“Yes lahd, thank-ye lahd,” one cries out in a heavy Caribbean accent. “We comin’ seeyuf and sahnd to Nu Yahk Citee!”

Her companion begins to sing, the first woman joins in and it takes me a moment to recognize the hymn.

“And He will raise you up on eagle’s wings,
Bear you on the breath of dawn…”

They’re clapping along, and the conversations around us pause in a kind of reverence. We’re all watching the skyline. 

Friday Night

The crowd is positively vibrating with anticipation, but the band doesn’t make us wait too long. Jim James, the singer, emerges wearing a starry cape and a nervous grin. His voice lofts into the heavens, he howls at the crescent moon hanging cold and distant above the metropolis. His bandmates — three skinny men with lank long hair and one chunky drummer with lank long hair — keep time as James croons the verses, then pause on a motif and build audible rooms around it. There are the inevitable build-ups, the shifts in beat and key that prompt groans of ecstasy from the crowd, who quickly begin to loosen up. Tall men sway back and forth, short women push out some space for ethereal dancing. I raise my hands toward the inky sky, fingers grasping a warm breeze, opening my body to the sonic energy pouring over us. I spend a decent portion of the show with my back to the band, looking over the faces of the crowd. I’m reminded of The Streets’ nostalgic homage to the club scene of Mike Skinner’s youth: “Arms wave, eyes roll back and jaws fall open.”

I’m not sure if it’s everyone’s first show since the pandemic, the first My Morning Jacket show in years or just the particular fandom that gathers around this band, but we in the crowd are on the verge of nirvana. James’ own voice is frequently in danger of being drowned out by the rest of us singing his own lyrics back to him and moaning at each new musical progression. 

“Again I stop the waterfall by simply thinking
Again I stop the waterfall before my breathing”

I’ve got my back to the stage again as the spotlight turns onto the roiling crowd. All I see is orange-and-purple lights reflected back in our eyes, glasses and teeth. This, I realize, is my church. It’s been eighteen months since my last communion, and I sure missed sharing this — whatever this is — with a bunch of strangers.

“Again I stop the waterfall by finally feeling
Again I stop the waterfall by just believing”

Saturday Morning

I’m looking at the skyline again, now lit up in early orange sunshine against a blue-bird sky. I position my bicycle just right against the railing of the Brooklyn Bridge, snap a photo and send it off to H and a few friends. The bike’s cracked rear rack is held together with zip ties, laden with two panniers carrying clothes, tools, cooking gear, a sleeping pad and a sleeping bag, while my tent and shoes are lashed to the top — it’s warm today, and I’m riding in sandals. My food, camera, water and other knick-knacks are stuffed into a bag wedged into the basket between my handlebars. The bike feels heavy and cumbersome on the bridge, quickly filling with tourists as the day begins to warm, but I’m on the move again.

Across the lower tip of Manhattan I ride, through canyon-like streets blocked by gatherings of cops and firemen and unmarked SUVs with flashing lights. Later, a friend will send a photo back to me that was taken from the exact same spot at the same angle from where I took the shot of my bike on the bridge. In it, shell-shocked New Yorkers are streaming on foot away from the skyline. And two buildings that no longer exist are spewing smoke into the same blue-bird sky. The earlier photo was taken 20 years ago to the day.

Away from downtown’s sombre pageantry, the city is going about its business as I push north along the Hudson River Bike Path, a pedal-powered highway. I cut back into Manhattan’s interior through Harlem — bike lanes on the boulevards, short cuts through residential streets — and roll across a bridge to the mainland at the Bronx. Here, piled and wafting beneath freeways, is the detritus that gathers at the edges of civilization: plastic bags spilling ancient trash across underpasses — junk mail and take-out containers and soiled shower curtains — and the same solid walls of fetid, musty funk that permeate all great cities, from Delhi to Bogota.

Speaking of Bogota, certain areas of the Bronx remind me of the hard-luck corners ringing the Colombian capital’s downtown core: monstrous traffic, pollution-stained skyscrapers, fast food restaurants sinking into filth and, despite it all, smiles and conversation glimpsed between the concrete and machinery on this Saturday morning. Ringing my bike bell gets grilled-teeth grins and waves from children.

Leaving Pelham Bay Park on the East Coast Greenway, a cycling route network connecting Florida to Maine.
Note the sculpture installation on the lawn to the right. Not pictured: the tennis courts, just out of frame to the left.
Feeling like a vagabond again.

If anything, the national trauma associated with the 11th of September — ritualized around words like “freedom” and “never forget” — seems to deepen the further I am from the scene of the crime. In suburban Connecticut, beyond the Bronx, the parklands at Pelham Bay and the old-money mansions on the shore, I’m riding along a street of cheerful, shabby houses leaning into their lawns. An old pickup overtakes me and then pulls into a driveway, where two teenage boys are hanging out in the front yard. 

“Hey dad, how’s it going?” the younger one says. 

His father looks like a middle-aged Fonzie: blue jeans, white t-shirt, rolled-up sleeves. He walks around to the side of the truck, leans against the tray and looks at his sons. “Tough day, boys. Tough day.” 

Another hedge fund mansion under construction.

Sunday morning

“You’d spend $20 just on breakfast? What a big spender.”

“I heard this place is good. And besides, we need a full belly — I can’t wait to get the Honda out onto the coast.”

I’m eavesdropping on the couple at the table behind me to practice my Spanish. They speak with the beat poet’s rhythm of central-northern Mexico, and they’re snuggling and bantering like any couple that’s just enjoyed a Sunday lie-in together. 

“Ay of course, the big man wants to play with his toy?”

“You think you’re funny, huh?” I can hear him smiling. 

At the other end of the diner, another conversation — this one in English — has been steadily gaining volume and now intrudes upon my Spanish study. 

“They ought to impeach him when they get Congress, but I don’t think they’re dumb enough to actually convict,” a man is saying. He looks like someone’s nice dad, red-faced and out of place in his glowing Sunday morning activewear. 

“Do exactly what they did to Trump,” another man agrees. He’s the owner of the diner. “Make him wear it.”

“That’s right. But like I said, you can’t convict,” the first man puts down his coffee and stares out from under his baseball cap. He’s got a dark look in his eyes. “Because you know who replaces Biden if he goes.” 

The diner guy nods, grim-faced. He understands. 

“I got a customer who’s… like that,” he says. He’s not speaking at the top of his voice, but he’s got that theatrical tone that projects throughout the restaurant. “She says she didn’t like Trump for what he said. Now I say, ‘How’s your paycheck?’ She says ‘bad.’ I say ‘So next time the Democrats put up a monkey in a suit, you gonna vote for him?’ She says, ‘Probably.’”

The man in the activewear rolls his eyes at the apparent insanity of it all. After a moment’s silence he slaps the table and, with a newly chipper voice, announces that he’s leaving. He owns a bunch of rental units in the area, he explains, and he’s got a showing. 

Silence reigns in his wake, and it takes me a moment to remember the couple behind me. They’ve stopped talking. A waitress — the owner’s teenage daughter — brings their breakfast. I finish my food and gulp the last of my coffee. The bike is leaning against a wall outside, waiting to take the road. I turn to face the couple, brandishing the restaurant’s only bottle of hot sauce. They’re sitting still, stone-faced, not touching, staring at the food cooling on their plates. 

“Quieren picante?” I ask, offering the bottle. 

“No gracias,” the man replies quickly. He doesn’t look up. 

Sunday Evening

I’m standing at the bar of a low-ceilinged restaurant, watching a waitress filling my water carrier from her tap. A trio of chunky, pink-faced men are playing bluegrass tunes in the corner. 

“These people came all the way from Las Vegas to see us play, how about that?” the lead singer says at the end of a song. His white moustache is quivering. The crowd is nodding. A few scattered claps. 

“I mean, he’s my brother but that’s neither here nor there,” he adds, and a man in a camouflage cap and narrow tinted glasses raises his pint. “He had a gambling problem, you see, and needed to get closer to his vice. I think it’s working out for him.”

The bladder’s full enough for me to cook, clean my pot and stay hydrated for the next 12 hours or so, so I thank the waitress and step out. I’m lashing it to my bike when a couple in activewear leans over from the beer garden and asks a familiar question. 

“Where’re you coming from?” 

“New York,” I say. They grin, and I feel myself grinning back.

“Where’re you headed?” 

“Boston. But I’m gonna camp on the Airline Trail tonight.” 

“You thirsty? Hungry? Come sit.” 

Tony and Cheryl are adventurers and teachers, living the quiet life in small-town central Connecticut until the summers, which they spend under the sun and the stars. They’re endurance athletes and it shows — they must be the fittest middle-aged folks I’ve ever met, and easily the youngest at heart. Tony’s the kind of guy who’s been everywhere and done everything. He’s bikepacked in Nepal. He taught outside Mexico City. 

And Cheryl — Sea Sea to her friends — well, Cheryl is just high on life.

“When’s your birthday?” she asks while Tony’s hobbling off to the bathroom. They’ve been out cycling all day, too. 

I tell her the date, adding that “I’m a Taurus.” It seems like the kind of information she’d be interested in. 

“Oh, I’m not worried about that,” she waves my star sign away. “I just like to know when people came into the world.” 

Skipping ahead to the Charles River, heading into Boston.
Taking sanctuary from the strip malls in central Connecticut.

Consciously being in the world is a big deal for Cheryl. Her highschoolers are back in the classroom for the first time since before Covid, and she says they’re burned out on screen time. 

“And they know it, too. Kids are smart. So I’ve just been telling them, ‘Put your laptops away. We’re gonna do a lot of reading, a lot of talking and a lot of listening.’” She’s got that soft, knowing voice of the teacher who doesn’t have to try to get her students’ respect.

A glass appears in front of me and Tony fills it with cold Coca-Cola. Cheryl insists I eat half of her veggie wrap. I’m relaxing into my role as the tale-teller. All day I’ve been cycling across the strip malls and industrial parks that blight central Connecticut. I’ve been hounded by trucks and covered in exhaust by motorcycle gangs. I’ve been turned down by campgrounds that don’t allow tents — “We’re an RV-only campground,” they say without a hint of irony — and yelled at by grown men from truck windows. But sitting with these new friends, listening to Tony’s story about making small talk with Nelson Mandela and catching the wild look of adventure in Sea Sea’s eyes as she slaps the bags on my loaded bicycle, it’s giving me life. They empty a cooler full of snacks into my food bag and then take off with a wave. 

Over the next week, Cheryl will text me a selfie of her and Tony hiking in western Massachusetts, a video of an Australian professional rugby player untangling a goat from a fence and a link to Neil Young’s “Harvest Moon.”

Heading into downtown New Haven.
Looking for Rory and Paris on the Yale campus.
Lunch on the Farmington Canal Trail, heading out of New Haven

Monday Afternoon

I’m sailing, floating, rising with the Airline as it lofts up onto the highlands of northeastern Connecticut. Earthen aqueducts send me soaring over deep, narrow valleys and ravines, a ramp skirting along a mottled country of gullies and hillocks. 

During the last ice age, glaciers ground down from what is now Canada, scraping out a series of north-south ranges beneath them like claw marks in the Earth. Long Island marks their southern terminus, an immense mound of earth bulldozed south by glaciers. The upshot is that crossing those ranges toward the north-eastern corner of Connecticut would be an ordeal of altitude repeatedly won and lost — if it weren’t for the Airline Trail. 

Built in the late 1800’s to shave an hour off the Boston-to-New York rail journey, the Airline was so-named because the route was said to be arrow-straight, as if you’d drawn a line through the air. Aqueducts carried the train out over the valleys and sliced through hillsides. The train was reportedly painted white with golden trim and so locals along its path, spooked by the sight of a pale engine chugging through the night, referred to it as “the ghost train.” 

Within several decades, however, passenger and freight trains became too heavy for the aqueducts. The Airline fell into disuse until, in recent years, the state of Connecticut has pieced it back together as a gravel rail trail for hikers, walkers, cyclists and equestrians. 

A cyclist’s superhighway.

It’s a shortcut, a portal into the highlands. My legs feel light and strong and the weight of the bike imbues it with momentum and a sense of purpose. Gravel crunches under my wheels. I’d had an early start, munching on oatmeal and looking out across a lake at a power station. The morning had hit a snag when I reached an unfinished section of the Airline. It was overgrown with weeds and transformed into a knee-deep stream, forcing me to dismount and splash through. 

The woods are quiet and still, transformed to swamp in places by the summer’s unseasonably heavy rain. Every now and then the trail nears a town and I spot the outside world — a noisy asphalt savannah studded with Sunoco gas stations and IHOP restaurants baking in the late summer sun. The pedestrians who crowd the trail near those towns are friendly enough, but I find myself exhaling as I roll away, back into the woods. 

North of Willimantic now, and getting close to lunch time. It might be the hunger gnawing at my belly, the sight of a Walmart surrounded by gas guzzlers outside town or the way that midday sun saps the colour out of this low, scrubby forest, but I’m feeling a mid-morning slump in my mood. Over the last three days the pattern has remained the same: wake up, eat and sally forth into the world, eager for adventure. Over the course of the day, traffic and headwinds and homemade “Biden stole the election” yard signs and office parks and a tiny hint of loneliness conspire to erode my will. (I have to say it: cycling in the suburbs just isn’t as fun.) Then, late in the afternoon, something will happen to lift my spirits. Yesterday it was an evening’s conversation with Cheryl and Tony. Tomorrow, as I enter the home stretch, it will be the sight of a cyclist outside Boston dressed in the green face and yellow zoot suit of Jim Carrey’s The Mask

Flying now along the Airline ramp into the highlands, gullies and woods and tea-coloured rivers rolling beneath my wheels, I start belting out the lyrics to any song I have memorised. It’s an eclectic list: Pink Floyd’s “Wish You Were Here,” Slim Dusty’s “Paddy William,” Johnny Cash’s “Tennessee Stud.”

I’m midway through Courtney Barnett’s new “Rae Street” and feeling something unravelling inside me — a coil that’s been pulling tighter and tighter over the last couple of years. Covid. Heat waves. Some stuff between my dad and I, apparently never to be addressed again. Spotting literal Chekhov guns at protest marches. My mum, sisters and nanna attending my wedding as heads on a screen. Almost three years since I hugged my mum. I feel that coil spinning freely now, feel it all coming out in this song — something nostalgic in Barnett’s semi-ocker drawl and her lyrics’ interplay of impotent despair against suburban ritual: 

“Light a candle for the suffering
Send my best wishes with the wind
All our candles, hopes and prayers
Though well-meaning they don’t mean a thing
Unless we see some change
I might change my sheets today”


“Next door the kids run amok
The mother screams, ‘Don’t you ever shut up?’
And there’s one thing I know
The sun will rise today and tomorrow
We’ve got a long long way to go”

So I’m leaning back in the saddle, pushing on the pedals, belting this out with streams running horizontal from my eyes to my ears, choking and sobbing through choice lines and then around a corner, of course, an elderly couple appears on foot. It’s much too late to cover up my mess and so I barrel on, waving merrily at their confused faces and shouting out-of-key that “time is money and money is no man’s friend” until my voice cracks and my back buckles, dripping tears on my wrists as I grip the handlebars. 


Lunch on the Airline.

It’s later, now. I’m sitting on a fold-out camping chair beside the Airline, which has turned stony and slowed me down. I’m munching on a peanut butter quesadilla and reading Barbara Tuchman’s incredible history of medieval France, the epicly titled “A Distant Mirror: The Calamitous 14th Century.” 

The interval of 600 years permits what is significant in human character to stand out. People of the Middle Ages existed under mental, moral and physical circumstances so different from our own as to constitute almost a foreign civilization. As a result, qualities of conduct that we recognize as familiar amid these alien surroundings are revealed as permanent in human nature. If one insists upon a lesson from history, it lies here, as discovered by the French medievalist Edouard Perroy when he was writing a book on the Hundred Years’ War while dodging the Gestapo during World War II. ‘Certain ways of behavior,’ he wrote, ‘certain reactions against fate, throw mutual light upon each other.’

I’ve been here for an hour, hour-and-a-half and I haven’t seen anyone except a handful of ants inspecting my leg hair, a gang of small birds promenading through the canopy and a deer wandering in the forest. I pull another wrap from its plastic sleeve and scoop peanut butter with my long-handled camping spoon, smearing the chunky matter onto the tortilla, which is still supple after a couple of days in my food bag and god-knows-how-long getting from manufacturer to supermarket. Thanks be to preservatives. 

I lean back from the e-reader, close my eyes and chew on my lunch, inhaling and exhaling through my nose. The singing and the crying has left me spent and empty. 

As I sit here, eyes closed and munching, some miracle of meteorology puts air molecules on the move through the forest. The sound of the birch trees bending and shuffling to make way, of millions of leaves fluttering and brushing against one another, is as soothing as a Queensland thunderstorm tumbling against a tin roof. The breeze caresses my cheek and neck, tugs a little on my eyelids. After the heat of the week, I catch a tiny whisper of distant winter on the air. It doesn’t necessarily feel pleasant, but it does feel like something.

Home again.

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2 thoughts on “Portals: Cycling From NYC to Boston”

  1. hello! nice trip!! Do you know a biking store where i could rent a bike in new york and then leave it in boston please? thanks!

    1. Hi Adele! I’m afraid I don’t know of any shops that allow you to leave their bikes in a different city. It is pretty easy to take bikes on Amtrak trains, though, so maybe it’s possible to take the train back to NYC after you’re finished?

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