Saturday, August 29th 2026 at 7PM

Join the Woodstock Fingerstyle Guitar Festival for an Evening Concert, 7pm-10pm at the Woodstock Playhouse featuring Gareth Pearson, Aleksandr Misko and Alberto Lombardi. Check out www.WoodStockFingerStyle.com for further included exhibition, competition, artist bios and Festival Details…

During the late 1950s and into the 60s, the Woodstock Playhouse directors instituted Saturday morning children's productions & concerts as well as midnight concerts featuring such artists as Tom Paxton, Peter Yarrow, Tim Hardin, Pete Seeger, Happy and Artie Traum, Billy Faire, and Jack Elliot. The Band, including Levon Helm, Rick Danko, Garth Hudson, Richard Manuel and Jaime Robbie Robertson, would record their album Stage Fright at the Woodstock Playhouse with Todd Rundgren serving as sound engineer. As the 1960s evolved and Woodstock found itself at the center of a cultural revolution, the Playhouse was host to the final concert in a series of performances known as the Sound-Outs in 1968. Produced by John “Jocko” Moffitt and generally perceived as a precursor concert to the Woodstock Festival held in Bethel a year later, the Playhouse concert featured Richie Havens, with additional performances by Jerry Moore, Don Preston, Major Wiley and Bunky and Jake. 

Throughout the 60s and 70s, legendary musicians and bands played at the Woodstock Playhouse, including Arlo Guthrie, Van Morrison, Orleans, Full Moon, Sonia Malkine, John Hammond, Holy Moses, Dave Van Ronk, Levon and The Band, The Montgomeries, Geoff and Maria Muldaur, Jim Rooney and Bill Keith, and after the burning and rebuilding of the Woodstock Playhouse: Leon Russell, Cindy Cashdollar, Jacke DeJohnette, Sonny Rollins, Peter Yarrow, Bethany and Rufus Cappadocia, John Sebastian, Natalie Merchant, Larry Campbell, David Bromberg, Richie Havens, Noel Paul Stookey, The Indigo Girls, Leon Russell, Well Strung, all of the amazing Headliners at the annual String Sampler Concert, and so many more. 

Additionally, the Woodstock Playhouse, established in 1938 by a member of one of Woodstock's Oldest Families, became a central hub for the launching of major careers on Broadway and in film and television, as it continues to do today.