Today’s guest post is written by another grandchild of Bernard Olcott, Grant.  In his essay, Grant sends the entire family up the Highway to Hell, seemingly always on yet another road-trip.  When not working as an investment analyst at Investure, Grant is a college student at Middlebury College.

I love cars. Well, I should rephrase that. I don’t know all the parts or mechanics of the automobile. I can’t say I have a clear picture of the new Ford Fusion in my mind. I’ve never been to a car show, and I’m only starting to understand the difference between a BMW and a Benz.

So why do I love cars? I love being inside them. I love the warm intimacy such an enclosed space creates between two people. I love the thrill of reaching a destination, the fighting over the radio station, the comfort of drifting in and out of a drowsy sleep in the back seat, and, especially, the long meandering talks, spur-of-the-moment debates, and random lectures shared among the four seats that draw my family closer and closer together with each click of the odometer.


He said he likes cars.  Here he is driving a 1966 Mustang, with his sister, Celine Olcott.

Cars conjure up nothing but good family memories. From the live turkey that somehow managed to wedge itself between the roof and the Thule box during my sister’s first highway drive en route to a ski vacation to all the times my Dad took us to school acting like a punchy cab driver (“that’ll be five dollars and 75 cents, please!”), we cherished our silver Audi, affectionately named “Rusty.” With each memory, I remind myself how lucky I am to have shared all that time and all those antics with the people most important in defining me to this day.

Rusty and roadkill

Rusty the station wagon and the roadkill.  We had to declare the turkey to Customs Canada.

Without Rusty, my life would lack the thoughtful moments of reflection my family shares. I’ve come to realize Rusty forced us to sit down and listen to one another, as the hum of the highway naturally lends itself to conversation. Through argument and agreement, we strengthen numerous bonds amongst ourselves, discovering a little more about everything along the way. Nowadays, we barely get to see each other, and, if not for newer four-door sedans, we would have much less time and place to talk.

Car talks typically extend far beyond the vapid “what did you do today?” conversation. As opposed to a phone call, road trips give us a topic-free time slot to talk about anything.

With each story, lesson, parable, blog post (as the case may be), video produced, kvetch festival, moose spotted, roadside delicacy found (like oven-toasted grinder sandwiches) via my Dad’s “truffle-nose” technique, snow-stuck car freed, roadkill, run red light, highway patrol car evaded, border crossed, Rolling Stones song played, ski trail synchronously skied, or dog food meal dressed up as advice, I felt more grounded in my family and, consequently, secure in my identity.

The famous “Eye of the Tiger” video, courtesy of Executive Producers Celine Olcott and Julia Russo, starring Grant Olcott.  Brief cameo of Rusty the car.

“Life is unfair,” my Dad has said countless times behind the wheel in his best JFK impression, gesturing with his hands while spouting off in a Boston brahman accent, steadily making me more at ease with life’s surprises.

“There is always some inequality.” Truer words were never spoken.

“Listen to your gut,” my Mom would often say, eyeing me in the rearview mirror, teaching me to trust myself.

I frequently find myself looking back to these instructive moments that remind me to be, above all, true to my family and to myself in my day-to-day life.

Many times, Rusty the car provided the perfect milieu for me to discover my voice, passions, and opinions. I remember one time when I spoke up to my Dad. After watching the movie “Super Size Me” earlier that week in 4th grade, I tried to convince him why we should not stop at McDonald’s — it will make us fat, it’s not even real food, and all the toys are made by slaving Chinese workers living in squalor. It was a moment when my personality began to shine through to my family.  And to myself.

I always itch to enjoy the soothing respite of a long car ride. Maybe it’s the memories they bear or the nice chunk of time I can dedicate to absolutely nothing other than watching the snowy or verdant paysage drift by. So rare in modern life.

Synchronous Skiing by the Author and his sister.

For whatever reason, when I hear the click of my seatbelt buckle or smell the car’s leather interior, the outside world that’s soon to be quickly fleeting past the windshield begins to fade, and I tune in on my own and my family’s thoughts. Each time I step out, stretching my back while savoring the fresh outside air, I look around in a moment of nostalgic satisfaction and see my Mom, Dad, and Sister — the people who’ve loved and cared for me my whole life.  They seem a little less like strangers.


Before all road trips, the Author advises motorists to fill ‘er up and check the oil.


  1. Great story, Grant. When I think of long drives from PGH to Cape Cod, I also remember fondly the meandering conversations and mind-games on the pike along the way. Your engaging story-telling and unaffected writing style do Tom Yankus and the Choate English Department very, very proud. Bravò!

    Liked by 1 person

  2. My apologies to spacing on Ed Maddox. I never had the good Dean as an English teacher but boy was he great in the classroom from all that I have heard.


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