Small Town, Big Talent: Teddy Chipouras Makes Music Beyond His Years

Teddy Chipouras looks like the kid next door, with his winning smile and a floppy lock of hair that keeps falling into his eyes. But the 18-year-old singer-songwriter has earned a reputation as a serious musician and a thoughtful storyteller who’s wise beyond his years.

Chipouras released “Rolling Hills,” his first EP of original music last week, performed twice at Leesburg’s Tally Ho Theatre this month and is garnering rave reviews for his indie-folk style.

Chipouras started playing area breweries as a sophomore at Woodgrove High School, but his musical aspirations got a big bump last spring when he

Teddy Chipouras
Teddy Chipouras

caught the ear of Bill and Cheryl Bunce, founders of the Buncearoo concert series. The Bunces were impressed by the teenager’s stage presence and musical style that broke the typical pop/classic rock mold of Loudoun’s winery and brewery music circuit.

“He picks his songs really well,” Bill Bunce said. “He knows where his voice belongs and he’ll stay in that pocket. … He’s very driven. You don’t often see that in someone his age.”

The Bunces have made an effort to promote Chipouras, inviting him to open for national touring acts like Nashville-based Paul Pfau at Buncearoo shows. Chipouras will also perform at Buncearoo’s Off The Record Music Festival slated for May 19-21 in Atlantic City, NJ. The Bunces also connected the young musician with Mark Williams of Sucker Punch Studios in Bethesda, MD, who produced the new record.

Chipouras can chalk up his success to talent and personality, with the extra benefit of coming of age in Loudoun County at a time when the area is turning into a songwriting hub.

“There are so many connections in the music industry around here,” he said.

It all started in the small town of Lovettsville in western Loudoun, where Chipouras lives with his family. He got his first guitar, a Squier Stratocaster, in fourth grade. The following year, his fifth grade teacher Darrell Cummings, also a musician, let Chipouras bring his guitar to class to play for his classmates.

Teddy Chipouras
Teddy Chipouras

Chipouras had a few music lessons over the years but is largely self-taught and now plays guitar, banjo, mandolin, keyboard and percussion (fans love his homemade suitcase percussion kit with a pedal drum and tambourine).

The Woodgrove High School senior often finds himself playing at venues where the audience is a generation or more older than he is. His own friends and classmates sometimes aren’t comfortable hanging out at the wineries and brewpubs he plays, Chipouras said, but he’s able to forge meaningful connections with fellow musicians and fans from his parents’ generation and beyond.

“I have a lot of friends who are 20-plus years older than me. … That’s what’s so cool about music—age doesn’t really matter,’ Chipouras said. “You can connect through notes, you know. You don’t necessarily have to be the same age.”

Michael Stephenson is a musician and co-owner of Mad Horse Brew Pub in Lovettsville and general manager of Creek’s Edge Winery just outside of town and books music for both venues. Stephenson said he was immediately impressed by Chipouras’ “stripped down acoustic” style and by his confidence as a musician.

“It’s amazing how comfortable he is at his age in his own skin. His writing is amazing to me—he writes as if he’s 45 years old. If you listen to the lyrics of his songs,” Stephenson said. “I’d compare him to more of a Bob Dylan-, Ray LaMontagne-type of storyteller. When you listen to his lyrics, they tell a story of somebody much older than himself that he couldn’t have possibly experienced yet.”

Part of that storytelling knack comes from Chipouras’ interest in history, which has long been a source of inspiration for much of his material.

“There are so many good stories that are so interesting to me in history,” Chipouras said.

He’s been embraced by the local songwriting community, including internationally known songwriter Todd Wright. Chipouras is one of several young people participating in a program to develop young songwriters at Wright’s Half King Studios in downtown Leesburg. Earlier this month, Chipouras played with Wright at a show at the Tally Ho Theatre and he returned last week to perform with another popular D.C. area songwriter, Jason Masi.

And while the teen has been mentored by movers and shakers in the Loudoun music business, he’s also becoming a mentor himself as host of Mad Horse Brewpub’s weekly open mic. The small-town open mic is a laid-back affair, with no sign up sheet or strict rules, and Chipouras often finds himself sitting in with participants.

Chipouras is headed to James Madison University next year to study in the school’s music industry program. And while he’ll be taking classes on the business side of music, he’ll continue to focus on his own songwriting and performing career. He’ll also be close enough to return to Loudoun for gigs.

Bunce, who works with a lot of big names as a concert organizer, sees the potential for radio play and touring opportunities and says Chipouras is definitely one to watch.

“Most young artists are influenced by others and over time, they find their own voice,” Bunce said. “Teddy’s got his own voice today.”

Teddy Chipouras plays Saturday, April 23 from 6-9 p.m. at Stone Tower Winery, 19925 Hogback Mountain Road, Leesburg. For details, go to

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