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In 2005, Ryan Montbleau and his band headed into Applehead Recording in Saugerties, New York, to cut their debut album. With nothing more than ambition and a relentless work ethic to their names, they bootstrapped the whole thing, maxing out credit cards to fund it themselves and launch their careers from the ground up. Twelve years, eleven records, thousands of shows, and 60 million Spotify streams later, Montbleau returned to the studio for a special one-night-only concert that would become the latest entry in his venerable catalog: Woodstock Sessions.

Montbleau’s been pouring his heart out in song since the early 2000s, when he first began performing around his native Massachusetts. He’d go on to collaborate with Martin Sexton, Trombone Shorty, and Galactic among others, and share bills and stages with artists as diverse as Tedeschi Trucks Band, Ani DiFranco, The Wood Brothers, Rodrigo y Gabriela, and Mavis Staples, but it was Montbleau’s ecstatic headline shows—often more than 200 of them a year—that solidified his reputation as a live powerhouse and an inexorable road warrior. NPR’s Mountain Stage compared his “eloquent, soulful songwriting” to Bill Withers and James Taylor, while Relix hailed his “poetic Americana,” and The Boston Herald raved that “he’s made a career of confident, danceable positivity.”