Drive In, Drive Out: One man’s road from passenger to driver.

Scott JosephsonScott Josephson is a native New Yorker who grew up on Long Island and moved to the Boston suburbs in 2007. He has predominantly traveled by train, plane, and cruise ship to over 30 States, Canada, the Caribbean, Western Europe, and Israel. He is the proud owner of his first car — a 2010 Prius named Jet and recently drove round-trip from Massachusetts to New York. When he’s not traveling, Scott works in product management for an educational software company.

Music has always been an essential part of my life from listening to records as a child to playing Super Nintendo games growing up while blasting the radio or cassettes from my portable stereo I can’t remember a time without a soundtrack.

I tend to attach tunes to a certain place and time; sometimes it’s based on a specific memory, like walking home from the train station in my hometown to Green Day’s American Idiot album. Other times, it’s based purely on my mood I’m a huge fan of “breakup” albums like Dylan’s Blood on the Tracks. And for what feels like forever, so many songs have propelled me across over 30 states while I sat on a train, bus, or plane or in the passenger seat of a friend’s car but never behind the wheel.

As a native New Yorker, I didn’t get my driver’s license until I was in my late 20s. I figured that I’d need it someday and it was important in case of an emergency. When I moved to Massachusetts, I hesitated for almost 3 years before even getting a car, relying on the generosity of friends, public transportation, and the overpriced single taxi company in my town.

Last Fall, I finally gave in and purchased a Toyota Prius. As a newer driver, I was hesitant to get on the road, so I started small: supermarket runs and trips to the nearest mall. Over time, I expanded my journey to visiting friends in Central Massachusetts, spending the night to cut down on the amount of travel. On Super Bowl Sunday, I decided to take the bold move of making the round-trip in the same day and, after I embraced night driving, there was no turning back.

A very good friend of mine and I have seen Dave Matthews Band in Hartford for the past 4 years in a row. Before this year, I always took the bus or caught a ride with him. Now that he lives in Manhattan and I’m a car owner, it was my turn to take a chance behind the wheel. It’s not a bad haul from the land of Jack Kerouac (Lowell, MA) to Hartford, but I knew that I needed some tunes.

Whenever I travel, I’ve got a set number of tunes for specific travel: Steve Miller Band works well on planes because of the number of songs about air travel (Jet Airliner, Fly Like an Eagle, Rock’n Me); Aerosmith always made sense when crossing the Massachusetts border and heading to Boston by bus; Bruce Springsteen’s songs speak of highway freedom (Born to Run, Thunder Road, Hungry Heart); and U2 sings you across the darkest night to deliver you to a place beyond where the streets have no name.

For the drive to and from Hartford, I built specific playlists to mirror how Dave Matthews Band plays a 2-night gig: a loud list and a chill list. One of the greatest moments of this journey was when Two Step came in just as I crossed from the Mass Pike tolls onto I-84 West. And after sailing home on the chill side, I felt relaxed and confident at my 200+ mile adventure that will surely be the first of many.

What’s next? Well, as I build momentum, I already have carved out an escape back to my hometown. Surely this can only lead to my ultimate Kerouac fantasy a cross-country jaunt from Boston to Phoenix. And one of my first stops is sure to be The Rock and Roll Hall of Fame.

Scott Josephson is a Twitter friend and fellow Dave Matthews Band junkie. While Scott’s pretty new to driving, he’s not lacking in travel experience. He’s been to way more DMB concerts than me.

Chris Cavallari

About Chris Cavallari

Chris is a longtime digital content producer based in Maine. Since 1999, he has been an early adopter and active participant in blogging, podcasting, and social media, and has been guiding small and mid-sized businesses in leveraging video, social media, and digital publishing to the fullest. With an avid love of travel and the outdoors, Chris started in 2009 to give him a platform to showcase his outdoors and travel adventures, and to help educate others in doing the same.