It started raining while we ate lunch in Erie, Pennsylvania
and ripped into our faces and seeped into our boots until we finally slogged into a
motel in Lakeville, New York.

While we sifted through our clothes to determine just how
waterproof our waterproof saddlebags were—about 70 percent, was the answer—we
turned on the Weather Channel to get the next day’s forecast. The guy came on
and prattled ruefully about a massive, stationary low-pressure system that
hovered over the entire northeast of North America and promised rain across the
region for the next week.

The attachable face shield I'd bought for the trip looked so absurd that I chose to use it only in the most extreme downpours. As I've always said, if you don't look cool on your motorcycle, you've failed to meet your primary objective.

My old college roommate Tom Gillespie gave me a look that said: Tomorrow
morning, it won't be too late to turn around, or change our destination. Tomorrow
evening when we’re in Montreal and at the epicenter of this circling
rainbomber, it will be. Why should we knowingly subject ourselves to certain,
daily misery? This was supposed to be a vacation, wasn’t it?

That’s why I didn’t have to reply: Of course it wasn’t supposed to be a vacation. Vacations are for
married couples and candy asses. Like all of Tom’s and my trips together, starting with a mad car ramble around Ireland when we were kids not long out of college, this was
supposed to be an odyssey. To turn back at the first sign of difficulty would be to turn back at the first sign of an odyssey.

And Tommy and I know travel difficulty when we see it. We
once drove to Las Vegas from Chicago without stopping: 27 hours and a whole
carton of cigarettes. We smashed up his International Harvester Scout while
four-wheeling in a strip mine in West Virginia, and as I went to start the
crippled vehicle to drive to a hospital to get Tom’s face stitched up, the key
broke off in the ignition.

This trip was inspired, at least for me, by a trip west 10
years ago, on which we bought that Scout, in Albuquerque. Actually, we bought
two Scouts, one for each of us. And we took two motorcycles. And returned to Chicago in two days, a
two-man caravan, one Scout leading the way (it had no brakes, so it was the
natural pace car) and a pick-up truck following, with two motorcycles in the
bed and another Scout on a trailer, behind.

There was a logistical improbability to that story that I wanted
to recreate with this motorcycle trip. And the rain, discouraging as it was, contributed to the built-in insanity of flying thousands of miles holding for dear life onto motorized bicycles.

Were we still capable of doing the
impossible?

After dinner at a roadhouse across the street and a fast six
drinks with an entertaining and equally fast-drinking young local couple, we borrowed
hair dryers from the front desk and went to sleep with them blowing into our
boots.

Soaked to the bone in Lakeville, N.Y.

Forecast, hopeless.

 

Unexpectedly, the next day was perfectly sunny and we were
off at 9:00, roaring over hills and cheerfully buzzing through the green towns
atop the Finger Lakes. The vistas grew vaster as we approached the Adirondacks,
and I thought of the crass entrepreneurial bumper sticker, “If you ain’t the
lead dog, the view never changes.”

Yes, it does, if you’ll only back off a little, and slide over.

Tom and I ride in a staggered formation, developed over a number of trips, that
has Tom in the left third of our lane, and me in the right third, one man ahead by anywhere from a bike length to 50 yards, depending on the terrain. No matter who's leading, we hold the lane positions, so that the follower can
briefly slide up beside to communicate.

Usually,
Tom is ahead to the left and I'm behind to the right, in a
comfortable slot that lets me see how fast he’s taking a turn or how hard his
bike bounces on a railroad tracks. He’s the more experienced rider, so it makes
sense he’d usually be in the lead. But sometimes I take the lead. And sometimes the lead switches back and forth in a way that, mesmerized by the road and the sound of our engines and the goings-on inside our minds, we hardly notice.

It doesn't matter who's leading, because it's not a race.

Riding side-by-side—that's as taxing in
friendships as on motorcycles. There’s no room for error left or right, and
you’re always having to adjust your speed to stay perfectly even.

No: If you know where you’re going, lead
the way. If I know where I’m going, I’ll lead the way. We’ll pull side-by-side
only in order to notify one another of urgent needs: we need fuel, we missed the turn, your bungee chord is dangling dangerously close to your rear spokes, how about let's stop for a beer at this lodge by this lake.

This begins a serial account of the three-week motorcycle trip I took in June and July. I hope the icon showing me looking sort of cool will visually separate this series from my usual posts, which usually portray me as anything but. I'm publishing these posts here—with a few photos and videos—for the enjoyment of any who are interested, but I realize they're off topic and don't expect them to be read by most of my Writing Boots audience. —DM

At 5:00 a.m. on Saturday,
June 27, I opened the gas valve, set the choke, turned the key and pushed the
starter button.

The Triumph hummed, louder and louder as it warmed up. I was more reluctant.

The night before, the world had begun
organizing itself to convince me I was making a mistake with this trip.

Knowing I was leaving before
she would wake up, the five-year-old Scout reached for me from her bed and, over and over, screamed “Daddy!” until I
simply had to walk away. Cristie and I sat on the couch gaping at idiots
talking to Larry King about Michael Jackson, who had died a couple days
earlier. I imagined but didn’t say that this is what people must do the night
before they report to prison.

I kissed her in the morning
in the dim bedroom light, pushing my lips into her cheek deeply. The comfort felt crazy to leave.

On the Kennedy Expressway riding south
through the city, the cool blue predawn light made everything look greenblue
and shiny as if it had been scrubbed overnight just to convince me I was on the
Yellow Brick Road, headed in the wrong direction.

And as I crossed the Skyway
bridge, the sun sat perfectly on the surface of Lake Michigan, bobbing like a
lost toy ball.

I knew I had more to lose
than to gain by attempting to ride a motorcycle thousands of miles on country
roads from here to Nova Scotia in hopes that in none of the infinite moments between now and my theoretical return
would a deer jump out of the woods, a board fall off a truck in front of me, a tire burst, a rookie mistake send me into the back of a car.

Three days before my
departure, at a family dinner out, my wife said quietly while Scout was in the
bathroom, “Please come back.”

The words sounded so sweet,
coming from my college sweetheart and my wife of 15 years, that it almost felt
that the trip was over, and I was already being welcomed home.

In the months and especially
the last couple of weeks before I left, a subtle finality came across all of
us: No, this probably isn’t the last
time we’ll see each other. But, maybe it is.

Unlike some adventurers perhaps, I
could neither ignore nor blithely accept that chance. This trip—my owning a
motorcycle in the first place—was in defiance of my father. “I’m still
fascinated by Harleys new and old,” my dad confessed at the end of a magazine
essay he wrote when I was a kid. “I guess I’d never own one because it would be
a terrible example for a son I don’t ever want to go near a motorcycle of any
kind. He’s got a good head on his shoulders, and I’d like to keep it there.”

That
my dad died six months before made my rebellion a betrayal. (Dad would soon take
his revenge.)

In any case, in the last two
weeks I had taken Scout to her first Cubs game, she and I had slept out on the
back porch one night, we had played together in a Father’s Day baseball game. I drank her in as I morbidly
wondered, and in some cases believed I actually knew, what she would remember
of these last days with her father.

Terribly melodramatic I
know, but that’s how it felt, and it mixed happily with spring-out-of-bed-at-first-light
excitement that I was feeling for the first time in a long time. And also new:
the eerie absence of that grinding, floating, someone’s-gonna-get-me, something’s-terribly-wrong
anxiety that’s been at me for the last few years now as the shrinking publishing
industry and then the global economy have made me fear constantly for my
livelihood.

I told myself this adventure
and the change it was making inside me made me someone more worthy of being missed, and would make me someone more worthy of having back home at the end.

I also decided that, if I was
going to be selfish enough to risk Scout’s life along with my own—I’d bought
life insurance, but State Farm doesn’t provide a new father—my part of the bargain would be to write her an honest account
of the trip and a candid self-portrait of her dad, at 40 and still searching. Maybe
she can read it when she is 40, in lieu of going to the time and expense and risk of
taking a three-week motorcycle trip away from her own family.

By the time I got off the
highway and jumped on Route 6 south of Michigan City, Indiana, what I
was leaving faded into the morning fog and I started to make myself at home, in
the journey.

The bike was still shiny as I stopped for a hamburger in Bowling Green, Ohio, bound for Cleveland.

When riding a motorcycle at night, what you mustn't do is "outrun your headlight." Meaning, ride so fast that you can't stop for obstacles that appear at the end of the beam.

When living, unfortunately, you inevitably outrun your headlight. That is, you live long beyond the last year of age you pictured when you were young, and still making pictures of your life.

At 30, I was still able to judge my life and to some extent even live it based on what I'd imagined it might be, what I'd wanted it to be.

But at 40—with a child but no parents, with a 15-year marriage and a 30-year mortgage, with a head full of dueling truisms and a heart where love and worry jostle senselessly for chamber space—I have outrun my headlight.

So along with my old college roommate who also turned 40 this year, I'm channeling all my uncertainty into a single line—a motorcycle track, from Chicago to Cleveland to Buffalo to Montreal to Quebec City to Fredericton, New Brunswick to Halifax, Nova Scotia.

I'm sure other people have traveled from here to Nova Scotia before, but finding a single road map has proven impossible. To see the whole journey on a single map, I have had to awkwardly tape together six sheets from two North American atlases. They make an ungainly diagonal, bottom to top, left to right. The scale of each differs a bit, so that once you get to Nova Scotia, the getting-back maps—Maine, New Hampshire, Vermont, New York—don't fit.

I’m hoping it’s a two-way trip. But it’s a one-way map.

In the beginning of Jupiter's Travels, the 30-year-old book about riding a motorcycle around the world, Ted Simon writes that after weeks of planning the trip as an enthralling obsession, on the eve of his departure "I looked at the absurdly overloaded Triumph … and had my first cruel glimpse of the reality of what I was embarking on. My vision had been dazzled by the purple drama of warfare and banditry. Now I saw, with awful clarity, that a large part of my life henceforth would be devoted to the daily grind of packing and unpacking this poor, dumb beast.

"'It's impossible,' I whispered."

I'm beginning to know how he feels.

Back here in late July ….

***

PROGRESS UPDATES

6/27 Chicago to Cleveland

6/28 Cleveland to Lakeville, N.Y.

6/29 Lakeville (over top of Finger Lakes and up through Adirondacks) to Prattsburgh, NY.

6/30 Trois-Rivieres, Quebec

7/1 Kamouraska, Quebec

7/2 Sheeiac, New Brunswick

7/3 Hawksbury, Nova Scotia

7/4 Ingonish, Nova Scotia

7/5 St. Peters, Nova Scotia

7/6 Louisbourg, Nova Scotia

7/7 Liscombe, Nova Scotia

7/8 Digby, Nova Scotia

7/9 Portland, Maine

7/10 Woodstock, New Hampshire

7/11 Nevermind, Vermont

7/12 Lake George, New York

7/15 Binghamton, New York

7/16 Warren, Pennsylvania

7/17 Cleveland, Ohio

7/18 Chicago