Plan the Route. Let the Road Write the Story — Part I

Sometimes life gives you a reason to put a little distance between yourself and the familiar.

Not necessarily to escape anything. Not necessarily to find an answer. Sometimes you simply need to change the scenery around your thoughts long enough to hear them differently.

So in September, I packed my BMW i4 with golf clubs, a mountain bike, fishing gear, camping equipment, a drone, my laptop, and enough technology to keep working remotely, and started driving north.

There was a route.

There were hotel reservations, golf tee times, charging stops, work meetings, and eventually a destination: Cape Breton, Nova Scotia.

But there was no scorecard for the trip itself.

🚗 The First Lesson Arrived at 1%

The first day should have been straightforward.

I drove from New Jersey to the Catskills and played the Monster Golf Club. I had originally booked a twilight nine, but I arrived early enough that I was eventually able to play all eighteen.

Then I made a ridiculous discovery: I had forgotten some things at home.

So I drove back to New Jersey, picked them up, and started north again.

That was when a series of small mistakes compounded.

I took the wrong exit. A charger wasn’t where I expected it to be. Cell service became unreliable. I waited too long to make the conservative decision.

Eventually, the BMW showed 1% battery.

I was in an area with almost no cell service and no realistic charging option.

I pulled over safely and managed to reach BMW roadside assistance through the car’s SOS system. A tow truck could come—but not until early morning.

Fortunately, I had packed for camping.

So on the first night of a trip that included carefully selected hotels and resorts, I unfolded my sleeping bag and slept in the car waiting for a tow truck.

It was uncomfortable, slightly absurd, and—in retrospect—an appropriate opening chapter.

Planning matters.

But so does knowing what to do when the plan stops mattering.

⛳ Vermont: Returning to the Route

After getting charged and recovering on very little sleep, I continued toward Vermont.

At Green Mountain National Golf Course, the trip finally began to feel like the one I had imagined. The course sits naturally among the Green Mountains, and by mid-September there were already hints that summer was beginning to surrender to fall.

The next day, after finishing work, I took the gondola up Killington.

The view was expansive, but what I remember more clearly is the feeling of finally slowing down.

For the previous few days, everything had been logistics: driving, charging, working, fixing mistakes, making tee times.

At the top of the mountain, there wasn’t much to solve.

That was useful.

Maybe clearing the mind isn’t about finding answers at all.

Maybe it’s simply creating enough quiet to hear the questions properly.

🚵 New Hampshire: The Day That Refused the Itinerary

The White Mountains were supposed to be relatively structured.

I worked during the day, then took my mountain bike to the trails around Bethlehem.

That part went according to plan.

The trails were excellent—quiet forest, enough technical terrain to make the riding interesting, and the kind of activity that forces you to pay attention to what is directly in front of you.

Afterward, I had planned to go fishing.

But by the time I finished biking, setting up the fishing gear, figuring out access, and dealing with licensing would have left very little daylight.

Then I noticed a local golf course nearby.

So I changed the plan.

I played nine holes instead.

Later, I ended the evening in an outdoor sauna overlooking the water.

None of that sequence had been designed in advance: mountain biking, an unexpected nine holes, then sitting outside in the New Hampshire evening.

Yet it became one of my favorite days of the trip.

That was when a pattern started becoming obvious.

The itinerary was increasingly useful not because I followed it perfectly, but because it put me in places where I could make good decisions when something unexpected appeared.

⛵ Newport Wasn’t Supposed to Be on the Route

The biggest detour wasn’t really my decision at all.

A few weeks before the trip, I learned that I had won a sweepstakes connected to the Newport International Boat Show: two nights at Hammetts Wharf, admission to the show, access to the Windward Lounge, and use of a BMW during the stay.

Without that prize, I almost certainly would not have routed the trip through Newport.

That would have been a mistake.

Saturday became almost entirely unstructured.

I walked through the boat show in the morning, explored boats, spent some time in the lounge, and then drove around Newport later in the afternoon.

There were stops along the coast, drone flights, photos and videos, and eventually dinner by the water downtown.

Then, at the end of a pier, I encountered a wedding.

It was a private event, and I obviously wasn’t a guest. But rather than being treated like an intruder, I was welcomed into the edges of the celebration for a little while.

The setting was beautiful. The timing was accidental.

And once again, one of the strongest memories came from something that had never appeared on the itinerary.

But Newport ultimately came to mean more to me than a boat show, a beautiful coastal town, or another unexpected stop on a long road trip.

Some memories become important for reasons that don’t need to be explained to everyone. They simply become attached to a particular place, a person, and a time, and you know that returning there years later will bring something back.

Newport became one of those places for me—a memory I know I will cherish for the rest of my life.

🧭 Solo Doesn’t Mean Isolated

This was fundamentally a solo road trip.

That mattered to me.

There is a particular freedom in traveling alone. You can change direction without negotiation. You can stay somewhere longer because it feels right, or leave because it doesn’t. You can play golf, ride a bike, sit quietly over dinner, or drive another hundred miles simply because that’s what the day seems to require.

But solo travel doesn’t necessarily mean isolation.

I’ve increasingly come to think that people are part of the geography of travel too.

A place is not only its coastline, mountains, architecture, or restaurants. It is also the people who happen to occupy the same small piece of the world at the same time you do, even briefly, even as strangers.

You can plan where you’re going.

You can’t really plan who you’ll meet there.

🇨🇦 North

On Sunday, Newport ended.

I pointed the BMW north.

I stopped in Freeport, Maine, for a lobster roll, charged again near Bangor, and continued toward the Canadian border.

By then, the rhythm of the trip had changed.

I was still working during the week. I still had reservations ahead. There were golf courses I wanted to play, places I intended to stay, and eventually Cape Breton waiting at the far end of the route.

But I was becoming less interested in whether every day unfolded correctly.

The first week had already included a 1% battery, a night sleeping in the car, a mountain-bike ride that became an unexpected golf round, a sweepstakes that rerouted the trip through Rhode Island, and a wedding I was never supposed to see.

None of those things had been part of the plan.

And yet removing them would make the trip less interesting.

Preparation creates the structure that lets improvisation remain an adventure instead of becoming a crisis.

Maybe that’s the balance I was actually looking for.

I started this trip thinking I was going somewhere.

A week in, I’m beginning to appreciate simply being on the way.

Plan the route. Let the road write the story.