Nashville singer-songwriter Bennett Woolsey continues to peel back the layers of early adulthood with his latest single, “Chevy Chase.” Blending heartfelt lyricism with a warm, understated sound, the track offers an intimate glimpse into the emotional shifts that come with leaving home and discovering who you are.
At its core, “Chevy Chase” is rooted in reflection. Woolsey transforms memories both comforting and painful into a thoughtful narrative about change, loneliness, and finding purpose amid uncertainty. His honest songwriting feels conversational, allowing listeners to connect with the emotions behind every lyric rather than simply following a story.
As the second preview of his upcoming EP, the single expands on the deeply personal direction introduced by “Cigarettes & Alcohol.” Instead of chasing grand moments, Woolsey finds meaning in life’s quieter experiences, capturing the bittersweet transition from youth into adulthood with sincerity and restraint.
Originally from Texas and now dividing his time between Nashville and Los Angeles, Woolsey draws inspiration from a life shaped by constant movement and exploration. His experiences traveling, living on the road, and embracing unfamiliar places have become the foundation of his songwriting, giving his music an authentic sense of perspective.
Bennett says, “I seem to have stumbled upon a quiet, but certain coldness that’s slowly unraveled in the process of leaving home, and attempting adulthood. The good news, however, warmth was found in the presence of songwriting, and the fire fueled by memories, good and bad.”
In support of his new music, Woolsey is currently touring across North America with rising artist Maryjo. Full tour dates are below.
Tour Dates
July 25 – Chapel Hill, NC – Local 506
July 26 – Philadelphia, PA – Nikki Lopez
July 27 – Washington, DC – DC9
July 28 – New York, NY – Mercury Lounge
July 30 – Cambridge, MA – The Sinclair
August 2 – Toronto, ON – The Drake
August 4 – Detroit, MI – El Club
August 5 – Columbus, OH – Rumba Café
August 7 – Cleveland, OH – The Mercury
August 9 – Chicago, IL – Ramova Theatre
August 11 – Denver, CO – Lost Lake Lounge
August 13 – Salt Lake City, UT – Kilby Court
August 15 – Vancouver, BC – The Wise
August 18 – Calgery, AB – Dickens Pub
August 20 – Seattle, WA – Barboza
August 22 – San Francisco, CA – The Faight Collective
August 23 – Los Angeles, CA – Moroccan Lounge
August 25 – Anaheim, CA – House of Blues
August 26 – Phoenix, AZ – The Rebel Lounge
August 28 – Houston, TX – Bad Astronaut
August 29 – Dallas, TX – Am/FM Dallas
August 30 – Nashville, TN – Cannery Hall
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