The Very First American Road Trip

The view from the top of Mount Holyoke itself.

As I’m enjoying my last couple of days with Jen here in the Boston area, Boots and I are gearing up for the next leg of our great Alaskan adventure.  This is where it really begins tomorrow when I sadly deliver Jen to Logan airport for her flight back to Austin and set out for the destination that defines our whole journey.  It only takes a glance at the map to realize just how far we still have to drive to get there; and admittedly it’s not just a little overwhelming.  But it brings to mind one of my favorite road trip stories, one that never fails to inspire me as I set off down each new highway of discovery and wonder.

It was May 18, 1903 at the University Club in San Francisco.   A young medical doctor from Vermont, Horatio Jackson, argued with another patron as to whether or not an automobile could be driven across the country from San Francisco to New York.  It had been attempted a few times but no one had yet even come close.  Horatio and his beloved wife Bertha had been visiting San Francisco and were due to return to their Burlington, VT home by train in a couple of days.   Neither had any experience with automobiles.  In fact, during this particular trip they had both taken their first driving lessons as an entertaining diversion.  Horatio was deeply inspired and fell immediately and permanently in love with this novel and crazy invention.  It was this love that drove him to wager $50 dollars that the cross-country trip could be accomplished and that HE could do it.  The bet was taken and the adventure began.

Having no automobile and no applicable experience with such contraptions, Horatio wisely enlisted the help of a local chauffeur and mechanic named Sewall Crocker.   With Crocker’s guidance he purchased a “gently used” two-cylinder, 20 hp Winton car and outfitted it with supplies for the trip.  The two then set off on an adventure to make history.  There were no roads, at least none designed for automobiles.  There were certainly no maps.  All they had to go on were the mistakes of their predecessors and an unwavering commitment to the task at hand.

The story is epic, and worth knowing in its entirety but I will only give away the ending here. 63 days and 800 gallons of gasoline later, the Winton, Horatio and Crocker finally rolled in to New York City.  They were loyally accompanied by a begoggled hound dog that Horatio had adopted along the way and named “Bud”.    History was made and the term “road trip” would soon begin to nudge its way into popular culture, one day to become a  quintessential element of the American experience.

Horatio lived a long and fulfilling life, passing from it in 1955, only a year before the Interstate Highway Act was passed and a mere two years before Jack Kerouac published On the Road.  He never collected the $50 from that acquaintance at the University Club back in San Francisco.

There are no more automobile adventures to match Horatio’s feat, but there remains something magical about setting off on a driving trip to new places.

Bud… because all great road trips need a great animal companion!

Even with a reliable map, places are only dots and names.  Each town looks exactly like the rest on paper, but as you roll down main street and see the buildings and the people that are uniquely Anytown, USA, as you return the friendly smile of the attendant at the local convenience store, the town ceases to be just another dot on the map.  It becomes a piece of you and the next time your eyes roll across the name you can say, “Oh yeah!  Anytown…  I’ve been there.”