From Planning to Execution, Road Trips Never Seem to Go the Way You Think They Will

(Image:  Unsplash )

(Image: Unsplash)

What’s the first thing you do when planning a road trip? Before picking out stops along the way, before deciding which places you’ll spend the night in, before figuring out how many miles you’ll travel and how many days and nights you’ll be away — before any of that — the very first thing you do is you give your road trip an epic name equivalent to the significance of the marvelous adventure you are about to embark upon.

Wait a minute, are you telling me you don’t do that? Do you realize the momentous opportunity you are forfeiting?! Everyone knows the most important aspect of the road trip is being able to blast all your photos on social media and make all your friends and co-workers (who are back home in their cubicles eating sad tuna sandwiches) jealous that they are on the clock and not living life to the fullest like you are! Throw a legendary road trip title on top of that and everyone you know will probably hate your road-tripping guts for at least a week, and if that isn’t something to be proud of, well…

I’m being facetious, of course, but the only reason I thought to write a post on the topic of road trip planning is because of two trips I took within the last five years, both of which had pretty darn epic names. The East Coast Extravaganza was a particularly ambitious road trip I planned at the beginning of 2015 that would see me through a good chunk of Ontario, Canada, and then through six states, including a two-night stay in a cabin in Vermont.

A couple years later, in the summer of 2017, I cooked up the Great Lakes Expedition, a trip that was supposed to see me make a great big circle beginning and ending in Grand Rapids, Michigan, with visits to Toronto, Ottawa, North Bay (a city in northeastern Ontario), and Sault Ste. Marie along the way.

Getting French with it in Quebec, March 2015

Getting French with it in Quebec, March 2015

Neither of those trips ended up going the way I had planned. After taking a number of road trips in the last nine or 10 years, though, I almost think expecting the unexpected can pretty much be counted on as the norm. Of course, it’s a little difficult for things to go according to plan when your plans were only half-baked to begin with. This was certainly the case with the East Coast Extravaganza.

The plan, which I began formulating in January 2015 after booking a cabin in Hartford, Vermont, had been to set out around 1 a.m. from Ann Arbor, Michigan, on a chilly March morning. I’d make my way across the very bottom of Ontario, cross into Quebec near Montreal for a hot second, and then take a nosedive south toward Vermont.

After two days there, making stops at the University of Vermont in Burlington and at the Ben & Jerry’s Factory in Waterbury, my next stops, in succession, were: Boston; Providence; three stops in Connecticut, including New Haven, Riverside, and Two Roads Brewing in Stratford; New York City; and, finally, Camp Crystal Lake (yes, that one) in Blairstown, New Jersey.

All of this might have been possible if I’d had a couple weeks — but I didn’t. I had four days and I was trying to do way too much. So what happened? The first half of my travels, getting from Michigan to Vermont by way of Canada, went just fine (if you don’t count the misplacement of my passport after crossing back into the U.S.), but after two days of exploring in the Green Mountain State, I spent a large chunk of the next two days in the car, just driving.

Two hours of a rainy Saturday were spent in Boston, but almost everything else — Providence, each of the Connecticut stops, NYC — was a mere drive through. And Camp Crystal Lake? Scratched from the itinerary altogether. After what amounted to about 10 hours on the road that Saturday, I found myself at a Hampton Inn in State College, Pennsylvania, watching Arizona destroy Oregon in the 2015 Pac-12 Men’s Basketball Tournament Championship.

Fast forward to summer 2017, and along comes my next great road trip idea, the Great Lakes Expedition, named as such because we were supposed to encounter every Great Lake save for Superior along the way. As fate would have it, my friend and I only ended up traveling to Toronto and Niagara Falls and back — a great trip in and of itself, but not quite the one I had initially envisioned. Time was again a factor here, but so was cash money as I was still a month away from beginning a full-time job.

So I’m still looking to embark on a road trip that turns out to be just as epic as the name I bestow upon it. And though I’ve written about potential cross-country road trips I could take in the past, I’m certainly open to anyone out there who has suggestions. If you’re hunting for road trip inspiration of your own, one good place to look is, a site that allows you to create an itinerary and find attractions and accommodations along the way.

Have any bucket list trips lined up? Any nightmares out on the road? I’m sure we’d all love to hear about your adventures (or misadventures) down below.