The Geographical Inclinations of Vermont Singer-Songwriter Kyle Woolard | Music Feature | Seven Days | Vermont's Independent Voice

Music » Music Feature

The Geographical Inclinations of Vermont Singer-Songwriter Kyle Woolard


Published February 19, 2020 at 10:00 a.m.
Updated March 30, 2021 at 4:50 p.m.

  • Courtesy Photo
  • Kyle Woolard

The rolling hills, wide pastures and winding dirt roads of Vermont's Northeast Kingdom make the tri-county area feel trapped in a time before smartphones, social media and 24-hour news coverage. It's precisely this raw geographical splendor and off-the-grid vibe that led singer-songwriter Kyle Woolard to settle in Glover.

"It's ripped out of the pages of a storybook," he says of the NEK while seated in his self-built chalet. The house sits on the edge of a hill overlooking a wide, snow-covered expanse. Flakes gently fall from the sky as a fire crackles in a nearby woodstove. The scene is desktop wallpaper come to life.

Woolard, front person of dormant indie band the Anatomy of Frank, was born and raised in Virginia. A slight Southern drawl clings to the blond 32-year-old's voice. He first came to Vermont on tour with the Anatomy of Frank in 2011 to play a show at Burlington's Radio Bean.

"I remember looking out at [Lake Champlain] and thinking, This feels like Switzerland," he recalls.

Woolard is a world traveler, having visited five continents. Though currently inactive, his band plans to physically record an album on all seven. They've already released North America and South America, with Europe waiting in the wings.

Recently, Woolard wrote and recorded his first EP under the new moniker Glorious Leader. The five-track assemblage of gossamer acoustic folk-pop, My Kingdom, dropped in January. It amplifies Woolard's wandering spirit and affinity for places unknown.

Woolard first laid eyes on the Kingdom after his 2011 Burlington show but didn't make the move until 2017. He says he'd wanted to get out of Virginia for a while, and an encounter with an infamous figure in Charlottesville, where he was living, pushed him over the Mason-Dixon Line.

Months before the Unite the Right rally in August of that year, Woolard claims he ran afoul of Jason Kessler, one of the alt-right demonstration's key organizers. Woolard says that Kessler asked him to sign a petition to oust "black supremacist" city councilor Wes Bellamy. When Woolard refused, Kessler called him a "cuck."

"He looked like a doughy frat boy," Woolard says of Kessler, adding that his disdain for the politics and general vibe of the South crystallized in that moment. He moved to Vermont shortly thereafter.

To pay the bills, Woolard works as a freelance writer, penning everything from medical articles to sneaker descriptions. But writing music is his first and foremost passion.

With Glorious Leader, Woolard says he wanted to create music that "contained no lies."

"To me, that felt like such a challenge, because lies rhyme really well," he says.

That's not to say that his previously written music was full of untruths, per se. But he says that, while the Anatomy of Frank's songs are honest, they also contain a lot of fantasy, or "fantasizing about living a different life."

My Kingdom's opening track, "Borderline," which refers to Woolard's proximity to the Canadian border, is an artifice-free treatise on his life at the current moment. Over fingerpicked guitar — the backbone of Woolard's music — he sings in near whispers about his new property, the surrounding landscape and the various places to which his closest friends have wandered. The song establishes a recurrent theme in his work: geography.

Woolard continues to drop geographical locations in "Onism," a song whose name comes from the website Dictionary of Obscure Sorrows. The term relates to a feeling of frustration of being stuck in just one body. As the song explodes into its urgent, fluttering hook, Woolard delineates a plan to keep traveling north, through Labrador and Greenland, all the way to the polar ice caps.

Later on, he closes the EP with "The Wide Sargasso Sea," a song about being stuck even though you feel like you're ready to be free. It refers not only to Jean Rhys' 1966 novel of the same name but to a still region of the Atlantic Ocean surrounded by four ever-swirling currents.

Wanderlust is not exactly what fuels Woolard's songwriting, though. He claims to be pleasantly afflicted with something he likens to synesthesia, a perceptual disorder that causes people to, among other things, taste numbers or hear colors. For Woolard, it pertains to locations.

"When I hear a certain chord, it'll take me to a place," Woolard says. "It'll make me almost insane with a desire to be there."

Though My Kingdom was completed in 2019, Woolard felt the need to let it incubate for longer than usual.

"[I wanted] to make sure that what I was doing was good," he says. "And I revised the ever-loving shit out of it."

He enlisted Iceland-based friend and collaborator Karl Pestka (known for his work with Icelandic folk group Árstídir) to add strings to the EP. But Pestka, credited in the EP's liner notes as adding "invaluable help," ended up becoming a de facto creative consultant throughout the EP's mixing process.

"My favorite thing about Kyle is that he's a master of restraint," Pestka writes in an email to Seven Days. "He leads listeners along through the song and arrives, at the last possible moment, at a satisfying resolution ... tastefully, without going over the top."

Woolard admits My Kingdom reaches a certain level of pop that he never thought he'd allow himself to express. Atop a foundation of acoustic guitar, he layers in rousing handclaps, maximalist swells of strings, twinkling bells and memorable, rousing hooks.

"Embracing pop gives me hope that I'm progressing as I get older," Woolard says. "[Becoming stagnant] is a huge fear of mine."

Though Woolard has been a Vermont resident for more than two years, he hasn't performed much locally beyond the NEK. But in his small community, Woolard has achieved a bit of local renown.

Andy Bouchard, who runs the DIY venue the Barrage out of his home in Holland, first heard of Woolard while standing in the checkout line at Vista Foods in Newport. Woolard has since become a regular performer at Bouchard's concerts.

"He has a distinct ability to captivate an audience with beautiful songs that embrace the full space allowed in music," Bouchard writes in an email. "He brings a humble blend of [his] international experiences to his tunes, which resonates with [listeners]."

"There's something bigger in the Kingdom than what's visible," Woolard muses, referring to out-of-the-way places like the Barrage. "It was slow at first, but now I feel like I have a more robust musical family than I did in Charlottesville."

Now that Woolard has mostly settled into his new life, things that used to stress him out no longer do.

"I don't need to always be fighting to have a manager [or] a record label, [because] I've got a pretty good thing going," he says. "That being said, if someone wants to manage me, I'll take it."

The original print version of this article was headlined "Kingdom Come | The geographical inclinations of Vermont singer-songwriter Kyle Woolard"