A Murphy's Law Road Trip to Montreal

Updated: Jan 22, 2019

(Don't mind the photo's blur. As I mention time and time again, this was a trip that taught youthful me many a-lesson. Step one: be better with photography).

The summer after freshman year of college, my high school best friend, Dan (who've you met before.....a few times, actually) and I planned what was going to be a magnificent trip to Montreal, Canada. Instead, we barely saw the city, lost a piece of his car, and got turned around by our navigational system multiple times.

In retrospect, perhaps an international road trip planned by two 19 year olds was destined to be a bit of a mess.

I flew from Minnesota to New Jersey the last week of August, for my bi-annual trip to visit him. I always went east rather than him coming to Minnesota because, well, he had the ocean and New York City, and I did not. We had tried to do a grand New England road trip the summer prior, but the boy somehow totaled his car going 25 miles (40 kilometers) per hour two weeks before the trip. A year later, he had been able to save up for another car (a convertible, at that), but neither of us had the income to do the grand trip we had planned twelve months earlier. So we decided to keep it simple: drive the seven hours north to Montreal, spend a day there, then leisurely make our way back through upstate New York. His mother kindly lent us her GPS unit, as this was 2008 and smart phones weren’t really a thing yet, and we headed off around 11am the day after I arrived.

We were barely a mile down the road when he promptly read-ended the car in front of us at a stop light. Cue a ten minute stop while insurance information was exchanged, and then we were off again.

We had set the GPS to “fastest route”. However, again, as this was 2008, there were no live traffic updates. In addition, 19 year old’s aren’t always known for their critical thinking skills. What I’m trying to say is, we did not question the GPS when it told us to drive straight through New York City rather than around it. This resulted in the ever-exciting experience of one of the worst traffic jams I have ever experienced. We sat on a highway in the Bronx for over three hours, roasting under the sun because Dan refused to put the roof up. I had a decent little sunburn because of that, while his Mediterranean complex was unscathed.

Finally, around 4pm, we escaped, a grand total of 77 miles north from whence we came. Happily, it was clear sailing from there. Unhappily, we were still five hours from Montreal. But it was a lovely late summer’s afternoon, and we ambled our way north through western Connecticut, Massachusetts, and Vermont. It was beautiful scenery, and lovely to watch the sun set over the mountains and forests of New England. We filled up the tank in Vermont’s capital of Montpellier, the smallest state capital in the country. And then continued onwards. Between bathroom and dinner breaks, it took us until nearly midnight before we finally arrived in the Canadian city.

And then our youth struck again. We had not pre-booked a place to stay (something I know many well-seasoned travelers do, but absolutely not me), and simply cast around for a flashing motel sign. Well, ok, we used the GPS. This was 2008, not 1998. It led us to the Motel de Fleuve, an absolute dump of a motel but it had beds and a bathroom, so who were we to complain. And for whatever else, the motel rests on the shore of the St. Lawrence River, near the Champlain Bridge. While Dan slept in, and then checked us out, I enjoyed the view of the river, the bridge, and the skyline on the other side of the river.

Once we had checked out, we drove into downtown with the expectation of spending the day there. Our plan was to head back to America that evening, and camp somewhere near the border. However, once we had parked the car and gotten Canadian money out of an ATM, we quickly realized that Montreal was much more European than we had expected, in that it was a Sunday and everything was closed! Now, right now at 29 I would have still gladly wandered around a deserted city, but at the time neither of us were much interested in that. So after a quick stop at McDonalds so that I could grab a Smarties McFlurry (my absolute favorite treat that I could only get at non-American McDonalds, and now nowhere has them anymore and it is low-key devastating), we headed back to America. Yes, that is right, we did that entire journey the day before for what ended up being an hour in Montreal. 19 year olds, man.

The border crossing had a bit of a line when we arrived. Dan wanted to put the top down, but as I had received quite the little sunburn the day before, I told him that our friendship would be over if he did such a thing. We compromised by rolling down the windows. Soon, we noticed a neighboring car gesturing towards us and pointing towards Dan's rear end. We both assumed a flat tire, but when we glanced out the window, we saw not a flat tire but instead a piece of the car hanging off. Just a strip of the side of the car. Hanging off. We both stared at it for a second, and then Dan quickly got out of the car, ripped it off, and threw it in the back seat. What a thing to happen at an international border! Also, to this day I am curious as to how a strip of fiber just came off of a car, but never matter. Happily, the Canadian/American crossing is a friendly one, and when they asked about it we all simply had a laugh.

We camped overnight in upstate New York (blog on that at a later date), and then continued onwards to New Jersey the following day. This time around, we simply followed signs to New York City. Once we arrived at the outskirts, we dug the GPS back out and input his parent’s address - with explicit instructions to bypass the city. We were told to get on the highway, which we did. We were then promptly told to get off at the next exit, which we did. We were then directed onto the ring road of a local shopping mall. Upon completely the circle, we were told to get back on the highway. Looking like the ever-popular “blinking blonde man” GIF, we got back on the highway, muttering about the GPS as we did. It did not tell us to get off the highway again, but it did alert us every time we were nearing a Home Depot store, despite the fact that we never told it we were looking for a hardware store. I tell you what, I do not miss the GPS days.

Someday, I hope to get back to Montreal and actually, you know, see the city. But I do not regret the weird little getaway I had with one of my best friends. And we still joke about that damn GPS to this day.