Kristin Olson and Sweeney E. Schragg of the songwriting duo Winterlark bonded immediately over their shared love of the Great American Songbook, the pop music fostered by the English invasion, and the tight harmonies characteristic of acoustic folk vocal groups. About the duo's debut single "When I Saw You Stranded There," Matt Micucci of Jazziz writes, Winterlark "pays tribute to The Beatles while evoking the charming repartee that Ella Fitzgerald and Louis Armstrong had on their fabled duet recordings."

The duo released their debut EP, also titled When I Saw You Stranded There, in October, 2021, in the midst of recording a follow-up EP, due out in spring 2022. The six tunes of the debut are narratives that reflect the emotions they felt during the year of its creation, by turns sassy, hopeful, pensive, nostalgic, and angry. "These San Francisco Bay Area singer-songwriters know how to tell a story," writes Kelsey Marlett of Two Story Melody. "Schragg and Olson's vocals blend together with cozy chemistry." And Kristian Gonzales reviewed the EP for Imperfect Fifth, writing, "The acoustic soundscape reinforces its cinematic nature as the duo performs with a playful and reassuring chemistry."

To their live performances, Winterlark bring the chemistry reflected on their recordings, "the bantering, laughing, ruminating, sparring, and liking each other," as Kristin puts it. With Sweeney on acoustic guitar and Kristin on upright bass, their spare, clean sound is voices forward, with an emphasis on their stories and their intricate, jazz-influenced harmonies.