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A Brief History of the Woodstock Playhouse

The reality of the Woodstock Playhouse grew from the vision of Robert Elwyn, a descendent of one of Woodstock’s oldest families. Elwyn emerged from his work as an actor, director and theater manager at the Maverick Theater as an independent visionary. So it was, with Overlook Mountain as backdrop, that Robert Elwyn turned to his uncle Arthur Wolven in the spring of 1938 to construct a theater based on the design of architect Albert Milliken. Unique in its inception, both inside and out, construction was completed in just 48 days, permitting the opening of 'Yes, My Darling Daughter' on June 30, 1938.

Over the next few years, as its standing among American summer theaters quickly rose, the Woodstock Playhouse received heralded praise for its performances.  In July of 1941, it became apparent that the Woodstock Playhouse had arrived in the pages of American theatre history books when Al Hirschfeld visited the playhouse to create a drawing of Robert Elwyn with famed “fan dancer” Sally Rand and his cast of ‘Rain’.  The drawing would appear in both the New York Times and the New York Daily News that season.  The Woodstock Playhouse stage also saw appearances by Karl Malden, Elissa Landi, Francis Bavier and Lillian Gish, first lady of stage and screen, to name only a few from the cavalcade of stars.

With the arrival of World War II, gas rationing took hold, and limited the arrival of summer visitors to Woodstock; the Playhouse went dark till war's end. Following the war, Elwyn sold the theater to Boston lawyer, Michael Linenthal, and answered the call beckoning him to Hollywood and the world of film.


In 1949, Margaret Webster, co-founder of the American Repertory Theater, brought her successful Shakespeare touring company to Woodstock.  Encouraged by the reception she received from Woodstock theatergoers, Webster returned to the Playhouse for the entire summer season in 1950.  The audience members who attended witnessed the professional stage debut of Larry Hagman, son of Rodgers and Hammerstein muse Mary Martin, and performances by acclaimed actor Leo G. Carroll and actress Eva Le Gallienne.  Years later, the theatre world is still abuzz with stories of how performances by Ms. Webster’s company inspired their love of and career in the performing arts, and these seasons are captured in photo and text preserved in the U.S. Library of Congress.

In 1951, the Woodstock Playhouse came under the ownership of A.L. Sainer, with Mrs. A.A. Champanier as publicity director. Sainer returned the summer season to the presentation of recent Broadway productions, including the occasional musical.  During Sainer’s time as owner, such rising stage and screen personalities as Anne Meara, Dick Van Patten, Robert Hutton and Heywood Hale Broun added their names to an already impressive list of actors who would add the Woodstock Playhouse to their many credits.


With the sale of the Playhouse to Edgar Rosenblum in 1960, the theater entered a new era. As the Playhouse continued to offer a combination of popular Broadway plays and a mix of classic and contemporary dramas, important theatrical names also found their way to the stage of the Woodstock Playhouse during Rosenblum's and Artistic Director Harold G. Baldridge's tenure, including Diane Keaton, Judd Hirsch, Estelle Parsons, Lee Marvin, Chevy Chase and Peter Boyle. 

During this time, Rosenblum also advanced the Woodstock Playhouse in new directions by instituting Saturday morning children's productions as well as midnight concerts featuring such artists as Tom Paxton, Peter Yarrow, Tim Hardin, Pete Seeger, Happy and Artie Traum 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 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 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.

In 1972, Rosenblum sold the Playhouse to Harris Gordon. Under Gordon's leadership, the Woodstock Playhouse continued to represent the best in Summer Theater. Programming would expanded to include offerings for children with the addition of the Joan Gordon Theater on the property and subsequent seasons’ performances would also feature appearances by John Glover, Mercedes Ruehl, Angela Landsbury & Janet Hayes Walker.


Following sale of the theater to Ralph Miller in 1986, the Playhouse offered a modest selection of Broadway musicals during Miller's years of operation. 

In 1988, with the Playhouse just one month shy of its fiftieth anniversary, Memorial Day dawned with the theater engulfed in flames. The completely wooden structure burned quickly and ferociously, lighting up the early morning sky over Woodstock. Unique for its architectural presence at the entrance to the village, the Woodstock Playhouse had served as the primary center of professional theater, music and dance in Woodstock for fifty years. When Woodstock awoke that morning, “the colony of the arts” understood immediately that more than a building had been lost. Though arson was suspected, no charges were ever brought in the destruction of one of Woodstock’s most venerable landmarks.

Despite the loss, the early vision of Robert Elwyn persisted and efforts began to return performances to the site he had selected for theater in Woodstock. Through strong community involvement and fund-raising efforts led by the Woodstock Arts Board – formed to oversee the purchase of the property, led tirelessly by Nancy Kislin, and the rebuilding of the Woodstock Playhouse  - the Woodstock Playhouse began to rise again. Beginning with a simple stage and outdoor seating, the new Playhouse evolved to include a representation of the original façade of Elwyn's theater designed by architect Les Walker. As efforts at fundraising continued, a structured roof was built over bleacher seating for the open-air venue and wing space was added.


In November of 2010, as the Woodstock Arts Board could no longer sustain and support the Playhouse, the Pan American Dance Foundation, a local not-for-profit corporation operating the New York Conservatory for the Arts for 25 years in neighboring Hurley, N.Y., stepped forward as the responsible guardians to purchase, preserve and complete the revitalization of the Woodstock Playhouse.

With Executive Directors Randy Conti, Douglas Farrell and President Diane Stein serving as guiding forces, the Woodstock Playhouse began a major renovation under the supervision of John Kostezko. Following construction, the fully enclosed, climate controlled theater was reintroduced as a year-round venue. The doors of the Woodstock Playhouse reopened in June, 2011 with a gala reception and performance of 'A Chorus Line' with an introduction by Ulster County Executive Michael P. Hein.


The Woodstock Playhouse, today, produces an annual celebrated summer stock season with its own rising professional company, at what has, once again, become known as a stepping stone to Broadway, acclaimed National Tours, and nationally recognized venues. The Playhouse is also host to a growing roster of annual events, festivals, headliners and extended performances.  During these transformational seasons, the Woodstock Playhouse stage has welcomed illustrious performing artists including Patty LuPone, Peter Yarrow, Bethany and Rufus Cappadocia, John Sebastian, Natalie Merchant, Larry Campbell, David Bromberg, Noel Paul Stookey, the Indigo Girls, Leon Russell, Well Strung, and Happy Traum. 

The Playhouse is a celebrated site of American Theatre History, carrying on its near century old tradition of lauded performances on the site which Robert Elwyn originally selected for Woodstock’s treasured theater at the gateway to Woodstock.

A more detailed history is on display at the Woodstock Playhouse and available for viewing when attending a performance. 


Special thanks to Richard Heppner the Woodstock Town Historian, The Historical Society of Woodstock, Ellen Densen, Leslie Dawson, Matthew Wright of Fig Tree Photography, Jane Raymond Ciarcia, Beth Abrams, Courtesy Galerie Johannes Faber and the Al Hirschfeld Foundation. 

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