Life

Meet The Couple About To Break The Record For The World’s Longest Road Trip

Grab a paper and a pen, I want to try something. Think about some things that have been on your mind for a bit. Goals or dreams that have been tucked in the farthest reaches of your brain. I’m talking about the things that, for one reason or another, you’ve never actually acted on. Once you scribble down ten or so, sit back and admire. You just took one step closer to accomplishing those long-dormant fantasies.

That’s the same first step that author and famed drifter Greg Cayea took before deciding that he and his girlfriend Heather Thompson needed to break a world record. Specifically, the world record for the longest domestic road trip. The two have been driving, almost non-stop across the U.S. for over 100 days now and have covered close to 25,000 miles.

On the tail-end of their marathon, world-record shattering, road trip the couple were kind enough to hop on the phone with us about their daily rituals, the lessons learned by living within arm’s reach of your partner for 100 days, and how the hell they’re bankrolling this whole endeavor.


How have you guys been?

We’re good, man. We’re taking a little breather. It’s been about 100 days. There’s all these rules that we have to follow, and one of them says that we’re allowed to stop in any one location for 13 days. We were passing by New York, and that’s where my parents live, so we’re basically restocking on food and coffee and all that shit.

Right on.

We got to be out of here by … Friday, I think, will make our 13th day? Then we’re going down to finish up the trip.

Where’s the finish line?

We don’t know. The Today Show contacted me to see if we could maybe make them the ending point on the actual show.

Oh dope.

Yeah, but it’s kind of a catch 22, because they need confirmation from Guinness that we will have the record. It’s a complex process. They want to make sure that we’re verified. I don’t know where the endpoint is, is the answer.

Did you ever play with the idea of going to Florida?

Yes. We’re going to Florida, actually. That’s our next stop. We’re heading down there. When I filled in the application [for the record]… There’s a two-step process. First you have to apply to break the record, and if you get accepted, then you have to basically submit your blueprint for how you intend to do it. If you get accepted for that, then they give you the green light and they send you the guidelines that you have to follow. During that process, they ask a start and an end location, because you’re not allowed to do a round trip. It had to be different locations.

Why no round trip?

In order — I don’t really know. I guess because in other countries … We’ve got a big country here. We think about it, and we’re like, “Why do they even consider that?” I guess it’s if you’re living in a smaller country like, I don’t know, wherever, Denmark, they don’t want you to be able to just keep going back and forth.

Oh just doing loops.

You’re also not allowed to backtrack for that reason as well. I don’t quite know the exact reason, but I think that that’s probably it.

For the endpoint, they did ask that, so I arbitrarily put in Paughkeepsie because it’s in the Hampton Valley. I love the Hudson Valley. It’s one of my favorite places. Right now that’s our endpoint, but I just hit them up. I said, “Can we change our endpoint?, and they said, “Yeah.” I’m just waiting to hear back from The Today Show to see if they’re going to allow us to do that or what.

And you can’t go into Canada or Mexico, right?

No, we can’t. A friend of a friend recently drove from… I think New York to Buenos Aires. We’re not allowed to do anything like that. We have to stay in the country. There’s been a couple times where we ended up on the border of Canada. We’re almost about to take a ferry [but,] if you cross the border, you’re automatically eliminated.

Oh, damn.

Yeah. The only thing they look at is the tracking footage on our GPS. If we were to even come anywhere close to the line … I really don’t know how it goes. There was one point when we were on the border of Mexico where my phone alerted me. It said, “Welcome to Mexico”, and I was like, “Fuck, no. I hope we’re not too close. I hope the highway didn’t dip into Mexico or some shit.” No, it didn’t.

Damn, that’s nerve-wracking. What started the idea? What sparked the need to go on the longest road trip?

Heather and I were living LA and we decided to move. I really wanted to do something interesting. I don’t know. She was real pumped up about the road trip, but I had done the New York to LA, east coast to west coast trip. I’ve been doing it since I was 14 years old. I grew up on the road. I was a troublemaker. I was always hitchhiking and all that shit. I had done it so many times.

I was looking at her excitement, and I was jealous. I was like, “Man, I wish I was excited because what? We’re going to drive on I-70 or I-80 or I-10 or whatever. We’re going to go through all the cities I’ve already seen. She’s super pumped and I don’t want to bring her down and not be super pumped.” She had never seen the country, really. Then I listened to a Tony Robbins audiobook, and that pretty much sealed the deal.

What book?

It was Awaken Your Giant Within. You do all of these writing exercises and shit, like “Are you living up to your potential?” “I don’t know.” “Well what would that look like? Take five minutes to write down everything that you would every want to accomplish spiritually, in business, financially.” On my list was break a world record. The second part of the exercise is like, “Now go back to that list and circle the top five” That ended up in my top five of the 100 things I wrote down, I didn’t know where to start, so I started Googling travel world records. Then Guinness came up, and I was like, “Oh yeah, Guinness. Guinness World Records. I used to fucking read that book when I was in second grade.” Then I found this record that we could break.

Basically, it’s the longest domestic road trip, but the technical term is longest journey by car in one country. I looked at it. It was 19,400 miles, but that got broke while we were on the road. The new record is now 22,406 miles, but we beat that. I was like, “Man, we could totally fucking redo this. It’s kind of my way way of breaking up with the road, really getting it out of my system and having something to show for it.” Heather and I also didn’t know where we really wanted to live, so we literally have gone through every small town, every big city, everywhere. We’ve seen it all. That’s it. That’s why. It got me pumped, and that’s like a vitamin for me.

It’s funny how people have to keep going harder and harder and harder to get a buzz they used to get biking down their own street.

Yeah. My life tolerance is pretty high, so I had to really pick something big.

I totally hear you. You say you were looking for a home base. Which is funny because I’ve gone on road trips doing the same thing with my girlfriend. No matter what you end it, and you’re like, “Well, now I just want to see more. I can’t find a home base now because there’s so much more out there.” Did you guys feel a bit of that, or do you know the spot?

Probably, man. It’s like that study that they did with … I think it was jam, where they set up 20 different flavors of jam at the supermarket, and then they do another exhibit where they only set up three flavors of jam. They sell way more because there’s less options. You don’t have to make those decisions. It’s the same deal, man. I used to love LA for the weather and the lifestyle. I appreciated New York for the same feel. Now it’s like every place is different, but it’s the same. You know what I mean?


You’re going to have to elaborate on that a little bit. I love the sentiment. But, I want to hear more.

All right. I used to love LA for the weather. Then I left, and I was like, “Oh, it’s cloudy out. That feels nice. Finally. The sun is not beating down on my head.” Then we were in Arizona, and I was like, “Oh, god, it’s so hot.” Then we would go up to Montana, and it would be freezing at night. “Ah, that’s kind of nice.” You sleep a lot better when it’s freezing at night, but it’s also shitty in the morning, whereas LA’s awesome in the morning. The pros and cons become equal in every single city and every single place. I used to think there is more pros than cons in LA and vice versa in other places until I realized just being outside in all of these places constantly that the pros and cons are all equal. They’re just different. No place is better, to me, it’s just a totally different way of living, totally different mindset.

I think I got you. Ultimately, anywhere you decide to settle on, it’s going to become home. With that, by virtue of being home, there’s going to be ups and downs.

Right. For me, it’s like wherever there’s community, that’s where the pro is. They did a study where the number one factor for longevity in life is being around people. It’s like no matter where we are, even in the dumpiest of place, in Creek Springs, Nevada, Elko, or wherever, you meet some people. You have a good time, and you have good memories. You really form the geography in your head. All its attributes are coming from me. They’re not actually coming from the place.

Heather, now that you’re here, I’ll ask you the relationship question. The highs and lows of being together all day, every day for over 100 days now. How does that affect your relationship? How’d you learn to work through it? What was the learning curve?

Heather: It wasn’t really that difficult. Sometimes —

Greg: Surprisingly, it wasn’t that difficult. Some TV networks wanted us to do … They wanted us to do a reality TV show about this thing, and we’re not about that kind of thing.

Heather: It was kind of boring. It’s like, “We’re fine.” Listening to podcasts and …

Greg: That was my biggest question. Before we left, that was my big fear: the relationship, but her fear is food.

Heather: That’s when I get the grumpiest. I’ll start freaking out if we can’t get good food, and half these places like the truck stops and places that we’re at we just have shit food. We’re eating hamburgers and fried stuff. That tests the psyche.

Greg: I’m a road junkie. I really didn’t think the road would be hard. I thought being in the same closed container with anybody would be difficult. I was really scared that it might tarnish the relationship for the sake of a prideful venture, I suppose. We’ve gotten into some fights, but for the most part, I think we pretty quickly realized when the other was grumpy. I’m grumpy at a certain time. She’s grumpy at a certain time. I know what makes her feel better. She knows what makes me feel better.

Heather: A big thing is dropping it. If we get in an argument, we move on real quick. There’s nowhere to go. We can’t go like, “Oh, I’m going out. I’m going to go for a walk.”

You can’t go into the other room.

Heather: There’s no escape.

Greg: We tried that. We were in Yosemite and we got into this argument, and I was like, “I’m going for a walk.” She’s like, “Well, where the fuck you going?” I was thinking to myself, “Where the fuck am I going? We have one car, we’re at Yosemite, there’s no service…” So, I get out of the car. I’m all pissed off. I go to the bench 20 feet away, roll a cigarette, I smoke it, and I was thinking, “Man, it’s hot out here. Maybe I should just go say sorry.” I got done. I came back two minutes later, and I was like, “Yeah, so, I’m sorry.” She’s like, “Yeah, I’m sorry.” That is pretty much it. It’s not avoiding the fights. I think fights are inevitable. It’s part of life. It’s letting it go. The key is stopping it at a commercial, not letting it narrate into a feature-length film.

That makes sense. That’s a really good way to put it.

I’ve come to find that road trips expedite relationship conversations. What else are you going to do but talk to each other? So you end up sorting through a lot of shit over the course of the trip…

Greg: I always tell everybody, “If you’re going travelling with your girl or your guy or whatever in an intensive travel venture like this, if there’s one thing, you’re going to find out you’re either going to stay together for a long, long time, or you’re going to break up immediately.”

Yeah, that will become apparent.

Heather: It’s like a test. You got to make it happen.


How are you guys funding this? I’m sure you get asked that all the time, but where’s the bankroll?

Greg: I was doing marketing and PR for other people as a freelancer. That was my way to travel and all that stuff. I put together a lot of money, and I saved it. I’m not a spender. I like doing PR stunts. I made a decision to stop doing PR and marketing for other people and to do a wild, wild PR stunt for my life, which was this road trip. That’s not necessarily the driving force behind it, but that’s in the back of my head. If it’s not worth writing a story about, I don’t really want to do it.

But, what I ended up doing, we were on the road, and money was diminishing. We swerved over in Lincoln, Nebraska. I have a blog that … It’s pretty well-read, not famous, but it’s okay. I swerved over in Lincoln, Nebraska, and I wrote a book. I published it, and that’s how we’ve been making money from that point on.

Heather: You finished the book.

Greg: Yeah. I had started writing the book awhile ago, and I decided to finish it and publish it and put it out to my blog list and see if it would take off. That’s how we’ve been paying for the rest of our trip since then.

Holy hell. What’s the book?

Greg: It’s called The Drifter Chronicles Volume I: No Direction Home.

I dig it already.

Greg: It’s a good book. You should read it.

You finished the book from the road? Damn, how long was the process of finishing it and getting it published and doing all that?

It was grueling. It was many, many hours. We were in Lincoln, Nebraska for about 10 days. I was writing for about 13 to 15 hours a day, at least. I put it out myself. I taught myself how to do it. It was on InDesign and Photoshop. I do all the illustrations. It’s flooded with cartoons and illustrations. I did the cover. I did it all.

Wow, man. That’s really inspiring.

Yeah. Now you can go and do that same shit.

Yeah. I got to get to Lincoln, Nebraska…

I got the spot for you. I’ll send you the address.

Did you guys get any advice going into the road trip that resonated with you or stuck with you?

Heather: It happened kind of fast.

Greg: It did happen kind of fast. The short answer’s yeah. I got tons of advice.

Heather: People said “you’re crazy,” more than anything.

Greg: Yeah. Every morning … I guess it should be noted I’m sober. I’ve been in recovery for five years now. A lot of that came into play. I have a big outreach group that if I’m ever feeling shitty, I have a group of people that I call. A lot of the advice I got were from people within that circle. The advice I gave to myself was to make sure that I stuck to my regimen I had before I left.

Which is what?

I wake up every morning at about 6am. I do 120 push-ups. I meditate for 15 minutes, and then I ask the universe to take care of me. That’s it. Every single morning, no matter where I am. Truck stop, rest area, national park, service fucking station on the side of the Jersey turnpike. It doesn’t matter. That’s what I do.


That’s incredible. Would you have any advice for someone thinking of doing something? Not trying to break your record, but someone going on a big road trip?

Heather: Plan. We did not do any pre-planning.

Greg: We didn’t?

Heather: No, we had two weeks, and then we took off.

Greg: What would we have done differently?

Heather: I don’t know. I guess I would have thought about…

Greg: Heather brought a lot of shit. I told her at the beginning. I was like, “You’re bringing a lot of shit.” I think what I would say is, “Don’t let the hidden gems pass you by, and you don’t need to travel to another city to find something interesting. You just need to open your eyes.” Here’s my advice. “Take a lot of photos. Stop. If you see something interesting, don’t just say, ‘Aw, man. That would have been a great photo.’ Turn around, drive back 5 miles. If you see a lake that you want to jump in, and you already passed it but you can’t stop thinking about it, turn around, go back. In the grand scheme of things–

Heather: Worth it.

Greg: The whole point of a road trip is to create a memory. You don’t know if it’s going to be good or bad, but you know it’ll change your life. You want to remember that life-altering experience that your building. I’m not a photographer. I never will be, but I would assume that 90 percent of photography is actually taking the picture and capturing the moment. I think that most people just drive straight through really interesting stuff. They don’t get off the exit. They don’t drive around the city. They don’t stop off at the exhibits or take a look at the small towns or pee in the middle of the highway when there’s no one on the road, any of that stuff. People are going from point to point. It’s just about being on that line.

Heather: Buy a National Parks Pass.

Greg: Oh, yeah. Buy a National Parks Pass. Buy a National Parks Pass. It’s the best investment you’ll ever have.


They’re what? 50 bucks for unlimited entries to everywhere?

80 bucks, and you not only get national parks, you get any national anything. National forests, national monuments.

Heather: Except Mount Rushmore.

Greg: Yeah, a few are not included, like Mount Rushmore. I think if it were a couple, my main advice would be to shut up and let it go after you get pissed and to make sure that you start every day new. Give the person you’re with a kiss before you go to bed, no matter what’s going on, and always get up and start fresh.

Heather: Yeah, I completely agree.

Heather, if you had to give a couple some advice, what do you think it would be?

Heather: Journaling. That’s something I wish I did more of. Fortunately, I have all these logbooks. People ask us, “What was your favorite place? What happened when you were here?” Sometimes Greg and I get in the car and we can’t even remember where we just were two days ago because we’ve seen so much. Being able to go back and read about how you felt or whatever, I think is important. Yeah, journals.

Greg: I’m going to try to make this into a book before I forget the details so people can learn what we learned and ride the journey with us without having to do it themselves. That’s basically touching on what she said.



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