Moonlighting: Will Overman

“The next time a hurricane hits, I just want to load up boards in my truck and go to the Outer Banks. Maybe put some shows together. My manager would love that.”

Singer-songwriter Will Overman drops that line as he talks to me over the phone, cruising somewhere in the Shenandoah. Touring on the whims of natural disasters, his manager’s blood pressure, and massive swells maybe isn’t realistic for Overman. But a man can dream big, and it’s safe to say he’s always thinking how he’ll find himself in the dangerous allure of nature again. He thru-hiked the Appalachian Trail before he started college and the relationship with his dad has been forged on many different adventures in surf and snow. His job is writing country confessionals that ring as true and clear as as polished whiskey tumbler, but he spends his days finding a wave to ride, a hill to climb, or a mountain to ski.

Some of that restless energy for adventure can be found in his music, like in the billowing road anthem “Dotted Line” off of his most recent Heart Pine EP, or the soothing “Traveler’s Promise” from his 2021 debut LP The Winemaker’s Daughter. But where music provides artistic expression for the Virginia Beach native, being out in nature provides existential reflection to remind himself how small and immaterial he is.

“Sitting on my board waiting for a wave allows me to look back on everything, and for one little moment, to not be a part of it. I think that’s something almost entirely unique to surfing. While I’m out there, I’m in someone else’s world and it’s both humbling and tranquil,” said Overman over email before our conversation.

Give Will Overman a dotted line and he’ll ride it out from town to town singing his songs, following it till there’s no more lines to follow, and the hum of humanity is drowned out by the enriched ambience of nature. There he can dream big under that big night sky, ready for his next adventure.

The following is an interview with Will Overman. It has been edited for length and clarity.

Where have you been adventuring lately? 

This past year was a lot of upheaval with my entire life blowing up, from getting divorced to going to Nashville. I’ve felt this constant beckoning towards the ocean. Part of that is familiarity and looking for a good place to land. But I got back in the water and it made me feel small. When I’m in the water I know I’m not in control and there is a freedom of that. I don’t feel that on land. It feels a little like, “Let go, Let God.” I’m not going to prevent anything from happening besides being smart and being the waterman I know how to be. There’s a really good feeling in that. 

There’s something about existing in that place where you aren’t supposed to be. I took avalanche courses when it came to skiing and there is no doubt about it, you are there just along for the ride. 

I just got back from Utah with my dad last week. Once you are back there, if something goes wrong there is nothing there you can do to prevent it. Hopefully you are trained well and things go right from there. My dad’s a snowboarder and I ski. We’ve been doing that together since I was five. It’s one of my favorite things to do. We’re such a great match and we push each other. It’s special when you can find something to do with a parent where your skill sets are kind of close and this is definitely one of those things. 

Photo Credit: Will Overman

How well do you know backcountry stuff? 

We’re out there hiking and post-holing or taking a CAT, out at this place we know called Powder Mountain. Skiing is the only thing I’ve done with my dad that’s really stuck with me. We’re lucky that we were in a place where we could learn that from our dad’s and be close enough to mountains and afford it. 

I only feel privileged and blessed when I go skiing because there is a barrier of entry, it’s expensive stuff. I was lucky and my parents were able to take me and I’m extremely grateful for that. My dad introduced everything outdoors to me, starting with surfing and going to the beach. I got my first board when I was seven or eight year’s old and that was the first sport he showed me. 

Who were some of the people who were your heroes? 

As a beach kid, there’s always the surfers that we idolized. I never thought of them as heroes, but I did fantasize about being a pro surfer or pro skater, but I couldn’t do a kickflip (laughs). My go-to has always been Scott Avett of The Avett Brothers. In high school, when I found music that made me want to do it, it was because of them. Scott Avett and the way he carried himself and the way the Avett’s go about themselves in general has always been very appealing. 

Photo Credit: Maggie Graff

For surfing, it seems you are starting to experience a new board, is that right? 

I’ve longboarded most of my life and it fits a Virginia Beach wave, which can leave a lot to be desired. It’s often mushy, it’s closing out, not a lot of juice, the base is small. It always made sense for what was at the beach. I by no means am a ripper, but I’ll charge anything and go out big and bite it. Longboarding gave me an opportunity to get out a lot and get waves, instead of going out with my buddies on potato chips, way inside and catching half-second rides. 

These past couple years I started riding one of my dad’s old Nolte boards, 6’10” I think. It’s a blast to ride and it paddles great, I just started going to that just for kicks. My dad had a bunch of boards stolen which was a bummer, but insurance stepped in and we had cash for new stuff. 

We went to a local shaper and we got this 6’2” made called a Screaming Eagle. It is the most fun board I’ve ever had. Channel bottom to it so you don’t feel like you’re surfing, you are gliding. It  needs a powerful wave to surf, so I’ve only gotten a couple good days on it. I know with a hurricane swell it will just be magic. 

Like fly fishing, I’m sure I’ll keep trying surfing my whole life. 

Could you share a little bit about the Virginia Beach surf culture you are tuned into? 

VB gets a bad wrap and people say it has no waves. That is not true (chuckles). VB is the longest, uninterrupted sand beach on the East Coast, so there are going to be a lot of sand bars. That being said, one year 42nd Street can be firing, then the next year the bar is gone. You gotta be willing to go anywhere, but anywhere is only a few blocks down from where you were last year. 

As far as the spots go, the jetty at 1st Street is always going to be firing if there is a swell. I only surf there during ECSC (East Coast Surfing Championship) with the contest; if I am surfing mushy, East Coast surf, I don’t want to deal with crowds. I’ll take the mediocre waves for myself. 

Croatan is across from the jetty and it breaks every direction, and that is a fun wave I just started surfing this year. It’s like a mini The Wedge that breaks well. 47th and 48th and 49th streets are the spot right now, that bar is firing. 

Two favorite spots are 84th and 85th street because it is a little more undeveloped than the rest of Virginia Beach, a lot of cottages and live oaks. The other place is Sand Bridge and it’s kind of the tip of where the Outer Banks start on the Virginia side. It’s got this Nag’s Head feel to it and the bars are great, and the wharfs are cleaner. There’s a lot of breaks and some secret spots on the eastern shore that get really big, but you gotta have a boat. I’ve even heard some guys towing in at Fort Story.

One thing I’d like to try over the next couple years is to create these multi-hyphenate trips where you pack in music and adventures and link them all together. There’s this dude Thes One, from People Under The Stairs, who put together a whole beat tape album that was done while him and his buddies were on a ship, surfing the Maldives. Have you ever done anything like that? 

The closest thing is I’ve walked up to hills in the Blue Ridge and filmed videos. I did carry a guitar for the length of the Appalachian Trail. My trail name was Six-String and I did make music out in the woods. I didn’t record any of it. I actually had this goal the past four or five years and going out into a cabin in the Blue Ridge and playing and filming it. Raw, stripped-down, by the fire, ambient noise. I’d love to do something of that nature. 

What led to you wanting to do the trail? 

I had done pieces of the AT and been on it for most of my childhood. My dad and I started doing an annual birthday camping trip when I was probably five, out by Skyline Drive and Shenandoah National Park. He and I had planned to hike the AT after high school. When I was a junior and heading into being a senior he took a more realistic look at it and he knew he couldn’t take six months off of work. 

I just set out to do it and did it and was very lucky to have a family that was the best base camp support team ever. My mom and dad would drive hours and package up food drops for me and help me with gear. At 18 I didn’t know much, but I at least recognized that I didn’t have any strings attached and could spend five months in the woods before I went to college. It was one of the best experiences of my life and one of the hardest things I’ve ever done. 

Photo Credit: Will Overman

I’d like to do it again in another season of my life. At 18 I was full of piss and vinegar, and I went at it with this mindset of I have to finish this trail, if I nearly kill myself. I had discipline, but not mature discipline. I’d wake up early, take my time packing up, then bust ass for the rest of the day at three to five miles per hour. Some friends would get up and leisurely hike for 10 hours. I’ll wake up at 8:30, be out by 11, and sprint all day. 

It created a frantic nature to it. I’ll think back to the trail and it was one of the more stressful times in my life because of the time crunch. When I wasn’t moving, I wasn’t moving forward. I’d like to do it later in life when I can, A) take advantage of the situation abd look at it with a different perspective and, B) take five to six months off of my life when I’m in my 50’s, 60’s, or 70’s. It’s a much different thing than when you are 18 and going to college. I’ve talked to those old timers on the trail and I really appreciate their perspective on it. They’ll wake up when someone wakes them up, pack up their camp, and hike until they get tired. If it’s eight miles, good, if it’s 18, that’s good too. It’s a good way to look at it and a good way to look at life. 

The first woman to thru-hike the AT alone was Emma Gatewood, and she was 67. But I understand what you mean about the time crunch. Your body literally wouldn’t survive being exposed in nature that way if you didn’t complete it in those specific months. It’s a mortal line you can’t cross. We are just at the whims of so much of nature when we leave the confines of these human areas we’ve constructed for ourselves. 

It’s so good for us. That’s why I think I’m always trying to live in a way that is connected to nature. It’s why I’ve loved winter as I’ve gotten older, it’s forced me to become uncomfortable. It shows me just a little bit of what it used to be with surviving. If you go outside in winter and you are not prepared, you are not going to do well. That’s what the trail was like; winter was coming and I had to complete the trail in a certain time within the seasons. I think in 2023, where we are in America, we’re so far from nature it does a lot of damage versus good. Where my day to day or well-being has been impacted by something bigger than me, like nature, I’m always happier for it. 

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