6 min

Boston to Provincetown, by bike

The annual Outriders event isn’t the fastest way to get to Ptown, but it might be the most satisfying

Checking in at the starting point, in south Boston.  Credit: Lesley Fraser

Starting point, Boston, South End
At 6am it is already 30 degrees. I take a swig from my water bottle and try not to worry that I’m already slightly dehydrated from last night’s celebratory dinner.


“Lesley Fraser.”

“Fraser . . . rider number 91!” the volunteer at the check-in table says, reading out the number-for-life I was given years earlier. “When did you first do it?”

“1989, I think.”

“There are only five people with lower numbers today,” she says as she writes “91” on my calf with her grease pencil. “First-time riders were in the 2000s this year.”

Two days earlier, on my 40th birthday, my partner and I made the drive across New York State and Massachusetts to the home of a friend I once worked with in Provincetown. Sixteen years earlier, I’d arrived in Boston for the first time, talked into doing the Outriders’ annual 200-kilometre ride from Boston to the tip of Cape Cod, to Provincetown, a kind of gay mecca, my friends explained.

At 24, I was at the tail end of a brief attempt at heterosexuality. At 40, I was eight years into a relationship with a woman who had brought me back to cycling, and my newfound fitness, combined with a general feeling of rebirth, made me wonder what it would be like to revisit the ride I’d done all those years before to the place that had come to feel like home in the three years I lived there.

My partner, a competitive cyclist, hooks up with a fast pack and is gone. My friend Jay and I click into our pedals and roll out behind a group from New York in matching jerseys. My legs feel rested and strong; the chamois butter smeared in the crotch of my cycling shorts to fend off the inevitable chafing feels disgusting.

As we roll through Boston’s still-sleeping southern suburbs, following the day-glo green arrows volunteers sprayed on the route the previous weekend, we get our first glimpse of Boston Harbour and smell the first tang of saltwater. Somewhere around Quincy the urban sprawl starts to feel more like small-town New England. 

58 kilometres: Checkpoint 1, Halifax
We stop just long enough to pee — a tedious process of emptying my jersey pockets, peeling off my jersey and pulling down the suspender-style bib shorts — and to grab bananas. Coasting through Plymouth (not where the Mayflower landed, Provincetown folks will have you know, but where the pilgrims resettled after wintering at the tip of the Cape), Jay tells me has no travel insurance (I’m shocked but remember that I did the same thing in my 20s — for the whole summer).

We’re on a grim stretch: I disliked it 16 years ago and I like it less now. There are no quiet roads approaching the Sagamore Bridge over Cape Cod Canal, and the terrain is gruelling: long, gradual climbs followed by sweeping downhills (only car drivers think this is a flat route). But finally, in the distance, behind the treetops, we spot the upper structure of the bridge.

Driving across the Sagamore, with its two narrow, car-packed lanes, can be nerve-wracking; walking across it, which the law requires of cyclists, is downright frightening. Given the choice of looking at the unprotected 30-centimetre drop to the pavement and its roaring traffic and the vertigo-inducing views of the canal 40 metres below, I take off my shoes, with their slippery metal cleats, and walk as quickly as I can in my sockfeet, staring straight down.     

100 kilometres: Checkpoint 2, Sandwich
The second rest stop is a rider favourite: we’re on the Cape, we’re halfway to Provincetown — and there are sandwiches! Peanut butter, PBJ, banana/Nutella and something that sends the New Englanders into raptures: the fluffer nutter, peanut butter with a bizarre marshmallow spread called Fluff. We refill water bottles and get back on the bikes, yelling heartfelt “thank-yous” to the volunteers checking the numbers of incoming riders. 

Sixteen kilometres beyond Sandwich, we’re pushed onto Route 6A, the Old King’s Highway. Sixteen years ago, most through traffic stuck to Route 6, and 6A was a pleasant ride along idyllic New England main streets. Now, with traffic volume choking all routes, it’s a short but stressful ride along a two-lane stretch with little to no shoulder and a stream of aggressive, impatient drivers in both directions.

135 kilometres: Checkpoint 3, Yarmouth
At the Yarmouth stop, I grab a fluffer nutter; it’s delicious. We’re back on the bikes quickly (one thing I’ve learned about my 40-year-old body is that warming up takes a long time, and I don’t want to do it twice). Away from 6A, I let my thoughts drift, knowing that one of the most psychologically challenging legs is ahead, a stretch that almost did me in the first time I rode. At this distance, a “normal” ride would almost be over and my thoughts would be turning to beer and steak; today, we have 70 kilometres to go, and the next 15 are a relentless up-and-down grind. I settle in to draft behind Jay’s back wheel and stare at his spinning feet, determined not to think about anything until we hit the Cape Cod Rail Trail stretch, 16 glorious kilometres of paved bike path through the forest.

164 kilometres: Checkpoint 4, Wellfleet
Reeking of sweat and our crotches, we gobble handfuls of salt-crusted pretzels at the end of the Rail Trail and grimly refill our sports drinks; I’ve drank so much, in a fruitless attempt to replace what I’m sweating out, that my stomach is in revolt. I know the worst hills — paved dunes, essentially — are still ahead, so I pull a gel shot from my jersey pocket. Viscous blends of pure carbohydrates and electrolytes, gel shots are, despite their manufacturers’ promises (“deliciously crafted to entice your taste buds!”), disgusting, especially when they’re hot. Feeling like a six-year-old choking down parsnips, I squeeze the gelatinous mess into my mouth and will myself not to retch.

I get another blast of energy a few minutes later, when LeCount Hollow Road delivers us to our first sighting of the Atlantic, a very inviting glimpse of the beach where the road deadends at a sandy trail; even from the top of the dune cliff we catch a whiff of ocean breeze — and turn left. Whether it’s the gel shot, my diligent training or heat-induced delirium, the dune climbs are painful but over quickly, and we scream with joy on the descents. I shift constantly on the bike, trying to ease the stiffness in my neck and shoulders and the burning of the saddle and to find a comfortable grip on the handlebars; muscles in my feet, calves and quads threaten to cramp with every pedal stroke. Occasional drifts of encroaching sand in the road remind us that we’re surrounded by dunes. At the top of the hill outside Truro, a thoughtful route marker has written “First sighting!” on the pavement, and sure enough, in the distance to our left, we see the Provincetown Monument peeking above the treetops. 

188 kilometres: Checkpoint 5, Truro
With just 15 kilometres to go, we consider skipping the final checkpoint, but tradition must be respected: it’s the brownie stop! Early organizers, knowing that at this distance the only thing that will boost a depleted body is sugar, kept the final rest stop simple and solicited batches of brownies from volunteers. Aside from water, Gatorade and some fruit, that’s pretty much all that’s available. On my first ride, I ate four. Today, Jay and I share one.

The final stretch is euphoric: we fly down the North Truro hill, with the water on our left and a tailwind at our backs. I’m like a horse that can see the barn at the end of long rides, so Jay settles in behind me and we sail past the endless rental cabins, through Beach Point, past the “Entering Provincetown” sign, over the rise, and there it is: Provincetown Harbour with the town laid out along its edge. We hit the Commercial Street/Bradford split and stay to the right, groaning at the cruelty of Bradford Street’s dipsy doodles. We grin like madwomen as those gathered at the Town Common — faster riders, their friends and families, our friends and families, volunteers — cheer us in.

“Rider number?” a woman with a clipboard asks. “Ninety-one,” I reply, already wondering if I’ll have the lowest number when I do the ride when I’m 50.