Wolff grew up in a house on stilts, fifteen feet above a Florida swamp. Summer brought symphonies of alligators, owls and frogs. But in Wolff’s recurring dream, it was always winter, and he stood beside a bonfire, singing to half-animal, half-human beings he called Winterlings. Two decades later, the Winterlings had come to symbolize life's deepest callings - the voices that beckon dreamers from the highway to the woods. He listened to the Winterlings and began painting for ten hours at a time, covering canvases with otherworldly beings.  

Around the same time, Amanda was called by the voice of the Earth. She grabbed her guitar, drove to Canada and worked on organic farms in exchange for food and tiny rooms where she wrote songs by candlelight.

After meeting at a Buddhist fire ritual, Wolff and Amanda drove from Florida to the Pacific Northwest where they soaked up ten years of rain and gave birth to over fifty songs. Singing from the depths of the American wilderness, The Winterlings shine their literary lyrics on subjects ranging from transgender Civil War soldier Jennie Hodgers to a friend’s double lung transplant to the life story of a housefly. 

Featuring acoustic and electric guitars, banjitar, violin and foot drums, The Winterlings have played the Lincoln Memorial in Washington D.C., CMJ Music festival in Manhattan, The Juan De Fuca Festival in Port Angeles, Fremont Abbey, The Bearsville Theater, Benaroya Hall, Appel Farm, SEATAC International Airport, The Tractor Tavern and Seattle’s iconic EMP (Experience Music Project) Museum for the 20th Anniversary of the release of Nirvana’s In Utero Album. They've sold out shows on both coasts and shared stages with Blue Oyster Cult, Frazey Ford (The Be Good Tanyas), The Maldives, Danny Schmidt and Cataldo. Winterlings songs have appeared in multiple film projects including Outdoor Research’s Tiny House Tour (“Belize”) and the Irish Documentary Jennie Hodgers produced by TG4 (“Jennie Hodgers”). 

Wolff and Amanda made an early album under a different name before releasing their first Winterlings album, The Animal Groom, in October 2010. The album hit #6 on the Roots Music Report Folk Chart. In January of 2016, The Winterlings released their second album, You Are Acres, to a sold out crowd of 250 at Fremont Abbey Arts Center. Just 10 months later they released their third full-length album, Poems That Live As People. The Album reached #21 on the Alternative Folk Chart. With new classics like "Be Kind To the Housefly" and "Crawlspace," The Winterlings continue to surprise and inspire audiences worldwide. 2017 has been The Winterlings' busiest year to date. In September 2017, following their performance at the Lincoln Memorial in Washington D.C. during the Restore Civility Peace Rally, The Winterlings released their fourth studio album, "American Son." The new album has been a fan and radio favorite, inspiring praise and continued radio play at such esteemed stations as BBC Radio Scotland.