20 Years Later: A Road Trip Story - Trek Light Gear

20 Years Later: A Road Trip Story

EDIT: I originally posted this story on my twitter feed and it was just featured in a Relix Magazine article - crazy! Thanks to all of you who have shared and amplified it - if you've got a similar story to share about music, road trips or life in general I'd love to hear about it in the comments below or on Twitter!

Twenty years ago. It’s crazy to even think that much time has passed.

Twenty years ago, I was a freshman at college in Hartford, CT and my friends and I were die-hard Dave Matthews Band fans. (If that's not your thing, just insert your favorite band when you were 18 years old and read on)

Dave Matthews Band Roanoke Virginia 1998 Stub

I had been going to Dave Matthews concerts since 1995, though I had been trying to see the band even before that. I'll never forget calling a nightclub (Lupo's in Providence) in 1994 and asking them if a 15-year-old could attend the show if I brought an adult with me.

The answer was no.

So instead of getting to see the band in a small nightclub in '94 right before they took MTV by storm, I had to settle for seeing them at a sold-out amphitheater just a year later in 1995. That was a very early lesson in not liking rules.

So here I am a few years later in 1998 and the band had just finished an album of never-heard-before songs (Before These Crowded Streets). None of the songs had leaked out yet and the buzz was strong about the album being their best yet. They announced that they were starting the summer tour with a home state show in Virginia and I knew it was a safe bet they’d be debuting many of the new songs there before anyone else had heard them.

Adventure called. I bought the tickets with no clue how we'd get there, I just knew I had to be there.

Hartford to Roanoke was an 18-hour round trip drive and not only had my 18-year-old self never taken a real road trip before - none of us had a car that could be reliably trusted to make that kind of trip. And we were far too young to rent a car.

Step 1: Find someone at school willing to let us borrow their car.

It wasn’t easy.

But surprisingly, here’s the truth: you can actually convince a friend you’ve known for less than a semester to let you borrow their car and drive it over 1000 miles into the unknown. You just need to supply them with a lot of beer.

5 dudes in a tiny car, here we go.

Step 2: When you can’t leave for a 9-hour road trip until after class, you need a place to crash along the way.

A friend of a friend was a freshman at Georgetown - perfect. Except, when we got in late at night we couldn't wake him up. Not without waking up the entire floor with our knocking anyways. Alcohol is a hell of a sleeping aid.

And that's when we decided to sleep in the study lounge.

Sleeping in the study lounge - Georgetown 1998

Those were the long straws, here's what the short straw looked like:

Study Lounge Sleeping Georgetown 1998

If you're wondering where I got the idea to start a lightweight hammock company, it's safe to say these photos do a good job of showing the pivotal moments that led up to it. 

Here’s a quick break to also remind you that in 1998 we had no cell phones, let alone smartphones. Our map was a highlighted AAA TripTik, which is great until you deviate from the course and have to find your way back.

Here's me calling home on a pay phone to let my folks know I wasn't dead.

Payphone Days 1998 Charlottesville Virginia

Our next stop was Charlottesville.

We geeked out on all the DMB 'history' we could find - it was surreal seeing all the bars, clubs, and coffee shops that had been the birthplace of all the live tapes I had been trading since '93.

Then, while walking around Charlottesville and thinking about how these music heroes once used to just wander around these streets like regular people - we run into this regular guy named Boyd. 

Boyd Tinsely Dave Matthews Band 1998 Charlottesville

What were the odds?

The knowledge that road trips are sacred adventures & that the journey is the destination was solidified for me in that moment. The road trip romanticism of Kerouac, Hunter S. Thompson and Cameron Crowe had become as real to me as anything.

Things were HAPPENING and it was obvious it was already a life-shaping trip and we hadn't even arrived at our destination yet.

Which is about when the reality of not planning things out kicked in for us.

We soon realized we had no plan for where to sleep that night and had run out of study lounges to sleep in. We needed a plan.

The show was a General Admission show & started at 2pm the next day (Bruce Hornsby & Robert Bradley opened) so we decided to give up on looking for a free place to stay and just drive to the venue, sleep in the parking lot, and line up early for the show so we could get in the front row.

I have no words (and no pictures) for what it was like sleeping upright in a small car with 5 guys who hadn't showered since Hartford.

Our necks and our backs were wrecked and the foot smell was a force to be reckoned with. But the thought of being front row for a show can fuel just about any fire - and nothing was going to stop us at this point.

And nothing did.

Later that day we found ourselves in the front row, getting squeezed and crushed by a crazy hometown crowd for a band that was on fire. Seeing any band or artist at a point like this in their career is epic - they knew the wave they were riding was big and the crowd knew it too.

Dave Matthews Band live Roanoke 1998

We held our spot in the front row through both opening acts, we held our piss, we dealt with the rain, and we had the time of our lives.

Dave Matthews Roanoke Virginia 1998 Panoramic

Did you know cameras in the 90's took panoramic photos? Awesome.

Miss you Leroi. (If you don't know, the sax player on the right sadly passed away in 2008)

The show was everything we had hoped for. We got to see the first live versions of so many songs that would become classics for the band - Crush, The Stone, Stay, The Last Stop, DDTW.

In the days before the Internet connected us all, that was everything. No one else would hear these songs until the album was released and that was awesome.

Also, I was really proud of this photo on my little crappy camera.

Dave Matthews jumping Roanoke 1998

As the show ended and we shuffled out towards the exit, I found myself walking past the gate to what I realized was the backstage area.

In that exact moment, the security guy standing at the gate took a few steps away to talk to someone, and you can probably guess what happened next.


Sneaking backstage? I had never done anything like that in my life.

Not knowing if I would get asked to leave, or get arrested for trespassing. I just knew that it felt like what I needed to do in that moment, and that all my friends followed and we were in it together.

And then suddenly there was Dave Matthews, the mythical hero of our 18-year-old music lives. 

Dave Matthews Backstage Virginia 1998

The fear began to really kick in when we saw how familiar everything and everyone was.

It was a hometown show. These people were mostly friends and family and people the band knew well. We were screwed.

And then he approached.

"Hey, how are you guys? Where are you from?" he asked.

So we told him.

He interrupted us moments into our story with a big smile on his face: "You're the guys that drove all the way from Hartford?! Boyd told me about you! I was hoping we'd get to meet!"

Our music idol just said he heard about our road trip and wanted to meet us?

Mind blown. This was the craziest trip of our young lives.

The rest of our talk was a blur.

When security finally caught on to our lack of badges he told them we were 'cool'. Whoa. We took a photo & chatted, he signed our ticket stubs - he was gracious & kind and the 5 of us walked away realizing we had met a music hero who lived up to our expectations. That's really something.


I learned a lot on that long weekend in 1998.

About following dreams, the magic of road trips, how human our heroes are, and how badly feet can smell in a car.

But most importantly, I learned in those three days that anything was possible if you set out on an adventure.

We had no cell phones, no idea where we would sleep, just concert tickets & gas in the tank (of a car that wasn’t even ours). And it all worked out better than we could have ever dreamed.

In the days after, Dave Matthews led to chasing Phish around. Then it was studying abroad in Australia and finding myself in Boulder, the unmarked dirt roads of Colorado, and starting a hammock business at 24 years old that kept me following that quest for adventure. (But, still, chasing Phish around)

The point is that this story could be about any band or any destination.

At some point, we all learn to love the unknown or we continue to keep fearing it. And in that trip, a giant part of who I am today took shape.

Embrace the unknown. Choose adventure. Take chances. Sneak backstage (just kidding?). Sleep in the car. Take road trips. Do things that scare you.

And always remember to live in a way that creates stories worth telling 20 years later.

It's never too late to start.

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