Saturday, May 30 2026

Doors 6pm / Showtime at 7pm

Reserved Seating Tickets:

$25 in advance ($20 + $5 handling platform charge) 

$30 day of show ($25 + $5 handling platform charge) 

Saturday, May 31st, Rock Academy presents their Best of Season show; featuring song selections from their regular season shows: Sly and the Family Stone, Soundgarden, 90s Goddesses, 60s Prom and The Music of David Bowie all performed by their amazing students on the same stage! The wonderful Woodstock Playhouse is the perfect place to see this show. This show will have assigned seating, so please get your tickets early. A great night for the whole family.

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 so today.