Just Short of a Century

The (almost) 100-mile ride to Montauk.

Words and photos by Gordon Macrae

There’s a phrase in cycling for “hitting the wall,” known as “the man with the hammer.” I feel very close to that wall. I feel like that hammer is wedged, at a very uncomfortable angle, up under my knee joint.

Let’s back up.

It started in the dead of a New York winter, after a plate of delicious Mexican food and a couple of beers, when I said to my cousin Elise that we should cycle to Montauk “when it gets a bit warmer.”

Elise is never one to shirk from a challenge—it is one of the qualities that I most admire about her. “Alrighty,” I think was her reply. “But I’ll need to get a bike.”

I thought the 100-mile ride would present an interesting challenge, an opportunity to test how far I could push my usually desk-bound body. Hell, maybe it would give me some time to think. About what, exactly, I wasn’t too sure. But still, the idea of some thinking time was nice.

We rode on, over the bridge to Rodgers Beach and along Dune Road with the sea on our right; a long line of houses stretching ahead of us to the Hamptons. I had consumed my last Clif Bar hours ago, along with my last energy drink at some point in the hour after lunch. But we had only just passed the halfway mark of our long ride to Montauk.

“I don’t wish to alarm you,” says Elise. “But we still have 40 miles to go.”

“What’s 40 miles between friends?” I shout into the wind, with what I hope sounds like levity in my voice.

As we whistle through the outskirts of Southampton, I struggle to remember the intrinsic motivations more clearly. Obviously we are riding for the glory and the Instagram posts, that much is a given. But other incentives are hard to come by. “Because it’s there,” seems too trite, too 1920s-Mallory-on-Everest. “Because we can,” is too glib, too privileged.

I settle on “because it’s a challenge,” and “because I don’t think I can do it and I want to prove myself wrong.” Which probably speaks more to my lack of self-confidence than my physical ability, but it’s still a challenge to think about self-propelling myself the length of Long Island on a bike. Particularly when the farthest distance I’ve ever ridden is 60 miles. Particularly when that time was five years ago.

Regardless, the ride out to Montauk is nothing special by New York cycling standards. The highest elevation gain is a mere 200 feet. The majority of the ride is a straight shot out along the southern edge of Long Island. Calling it a “challenge” is to stretch the definition of that word among the cycling elite of a city that prides itself on being the fastest and the best.


Throughout the ride, I discovered that cycling generally encourages humility. There are highs and there are lows. Sometimes these highs and lows occur simultaneously. As we uptick the miles, I realize the trick to overcoming any overwhelming task or problem: concentrate on the 10 meters in front of you. And eventually, those meters compound to miles and the journey seems less overwhelming.

Whether we make it to Montauk by 6 p.m. or 9 p.m. doesn’t matter; we know we’ll make it there. But then, on the far side of Southampton, Elise’s bike grinds to a halt. No amount of engine oil from the Speedway garage outside Water Mill can save her chain. It’s game over. To say the last 20 miles—riding in the back of a taxi with our bikes in the trunk—was a failure would be to undermine the distance we traveled before mechanical failure put paid to our trip.

Still, it feels like defeat, and the first glimpse of Montauk as we crest the hill in the Hither Woods Preserve doesn’t feel nearly as sweet as if we’d ridden it. I think about how enjoyable this stretch would have been with the gently curving tarmac, the sun setting behind us, and the ocean off over to our right. Regardless, we vow to return later in the year, and finish it in one piece.