The “No Plan” Plan

When work starts to weigh you down, the need to escape enters your mind. And then, after hours of stress-inducing clicks through booking websites, airlines, hotels, restaurants, and weather reports, your credit card is worn out, you feel less prepared than when you started, and you’re ready to crack a beer and call the whole thing off.

Well, there is another way to get your travel fix: Pick a direction, start your car, go. I’ll show you how it’s done.

For this adventure, I chose North. Halifax, Nova Scotia was a place I’d only heard stories about from friends and seen pictures of in Outside Magazine. As it turns out, it’s far from Montauk: Just under 1,000 miles of road away on the eastern coast of Canada. On December 23, 2015 at 2:29 a.m., my copilot (and loyal dog) and I eagerly jumped in my truck. She probably thought it was weird to be heading to work so early.

And go.

Somewhere in The Bronx – 40.8017° N, 73.7933° W

I crossed the Throgs Neck Bridge in the early morning darkness and looked out to my left towards the lights of New York City. Surely, my friends were still out partying there. I recalled some good-time memories and laughed to myself as I paid the toll, then found a spot to pull off and let Skydog stretch. My coffee had turned cold, but I sipped it anyway.


Portland, Maine – 43.6667° N, 70.2667° W

Pulling into Portland at 11 a.m. felt just like driving through Montauk in the early morning. Fog engulfed the town and I could barely make out dock pilings in the harbor. The vibe was very old-school-fishing-village-near-the-water, with craft beer shops and restaurants giving locals and tourists a place to grab a pint and a nice meal. After walking the empty pathways along the Eastern Promenade, I found my way to Allagash Brewery, where I traded some beers with the bartenders, then called it a night after a gallon or two of Belgian Ale and found a hotel to sleep in.

On Christmas Eve, I woke up at 4 a.m. to load up the truck in Portland’s morning darkness, then drove North on Franklin Street to Interstate 95. I felt happy and awake, taking in the scenery as dawn crept over the mountains of Maine. By the time I slowly approached the border, it was 9 a.m. and no one else was around. “Bienvenue,” the nice officer said with a smile. A few, quick questions, and I was back on my long, winding journey. 328 miles to go.

The nice thing about a long road trip is that your mind wanders. I thought a lot about work, relationships, life. Rather than avoid certain ideas, I let go, and focused on how this journey would make me a better person.


Halifax, Nova Scotia – 44.6478° N, 63.5714° W

Destination reached. I navigated the quiet streets of Halifax towards a pet-friendly hotel in the heart of the city. Thankfully, the lights were on (they were open) and I managed to get a room (I had no reservation). Laying down on my bed, eyes shut, I reflected on the trip so far.

Look back at the hours you spent on the road dreaming and being inspired by the endless beauty in front of you. Keep a journal of your thoughts along the way–it’s a resource that will come in handy in the future.

Later that night, I meandered through the mist-heavy alleys of Halifax and saw bright Christmas lights in front of dark, closed restaurants. I turned down Argyle Street, a cobblestone stretch a few blocks up from the harbor, and noticed a dim glow coming from what looked to be a pub. The Shoe Shop was open–and fairly busy. I took a seat at the bar and scanned for a local beer (something I do in any new location) from one of Halifax’s three breweries. I ordered a Propeller Brewery ESB from a bartender in a Mrs. Claus costume with a friendly smile. Christmas morning would come soon.

In any unplanned journey, take time to share stories about where you come from, and ask the locals
questions–you’ll most likely find some common ground. Also, always offer up a smile. It goes a long way.


Martinique – 45.5820° N, 61.0541° W

I woke before sunrise to venture north of the city towards the endless rocky coves that I had heard about. I made sure I had my camera, wetsuit, surfboard, and some food: If there was a wave along the way, I wanted to be ready. The sky was pink in Halifax, but as I drove, the altitude dropped and a heavy fog–pea soup fog–set in for miles. Hello again, Montauk. I drove 50 more miles on Route 207 towards Lawrencetown and an area called Martinique. Every time I felt inspired by a new view, I stopped. This region was unlike the city: It was a perfect mix of forest and water. I stopped a lot. And then, as I neared Martinique, I was flagged down by a burly, upset-looking local in a lifted, red, Dodge pickup truck.

“You from around here?”
Not really knowing what a smart answer was, I told him the truth. “No, I’m not.”
“Well somebody has been screwing with my garbage the past three nights.” Expletives then went flying.
“Sorry to hear that.”
“Don’t you be sorry. You didn’t do this,” he said, pointing to a busted pile of wood near his driveway. “But I have a camera and when I find out who did this I’m going to burn their house down.” Then, he peeled out and we went our separate ways.

In an adventure, you have to roll with whatever happens. If you cross paths with an angry local, just be sure to remember that you’re the outsider in their town. Show respect and things will work out.

Finally, I spotted the beach parking lot entrance. A sign read, “Park Closed Do Not Enter.” So of course I entered and drove down the gravel road, smelling the salt air that I grew up with. Parking my truck in front of a dune, I got out and stretched, and like a rocket, Skydog leapt over the dune to dig in the sand, throw seaweed, and chase gulls. The beach is her favorite place on Earth. But there were no waves. Gorgeous coves covered in rocks for as long as I could see, with pine trees lining the hills that met the beach, but still, no waves.


Tea House – 44.643596° N, 63.35488° W

Back on the road, I spotted the house I had written about earlier in my journal: “Take Highway 207. There will be a big solitary house on the hill, called Tea House. A left point underneath. Explore this place, it is amazingly beautiful.”

There are no wrong turns in an adventure. Always move forward.

I parked at the bottom of the large hill looking up at the high-perched building, then walked up a wet and slippery path to the most beautiful sight: A rocky point led into a huge cove of chest-high waves that five surfers were already in. I ran back to my truck and suited up, cracking the windows for Skydog. I watched where one guy paddled out and then followed him, swimming through the unseasonably warm water. I pulled back the hood and waited for a good set, letting the locals–who had now dwindled down to two–grab a few. Then I saw the horizon rise as the next set neared me.


I may have woken up on Christmas morning without a tree, my family, or my friends near me, but I felt like I was given the best present I could have asked for: Perfect waves in a foreign land. I paddled and easily slid in to the wave, bottom turning and setting up for a long section that allowed me to carve turns well into the base of the cove. I kicked out as one of the other surfers gave a hoot in my direction. We traded waves for hours.

Returning to the parking lot, I opened up the tailgate to my truck and reached for cans of Montauk Brewing Company beers, sharing them with the guys who had just shared their home break with me. Life was good.

Peggy’s Cove – 44.4928° N, 63.9175° W

The afternoon sun was dropping, and I wanted to catch the sunset from the south of Halifax at a place called Peggy’s Cove. The pinks and reds were starting to flicker just as I approached it, and I could tell the night’s show was going to be a good one (it’s a skill all Montauk locals have from overlooking Navy Road).


Skydog and I jumped out of the truck and ran up to the base of Peggy’s Cove Lighthouse, a relatively small lighthouse that was perched over the ocean. Other tourists were also taking pictures while traversing the large, weather-worn boulders as the rising surf crashed beneath them. I sat down on one of the flat rocks, took in my surroundings, and fell in love with the place.

I stayed for an hour after sunset as the groups of people slowly left. I was the last person to drive away, heading back towards the city in search of Christmas dinner.