In early 1974, in its very first newsletter, Pentangle Council on the Arts, a newly formed Woodstock organization, opened with an explanation of its name. “Why PENTANGLE? Well, since we have a five-pointed program, the pentangle, a five-pointed star, seemed most appropriate. Our five concerns are the arts, humanities, education, appreciation, and participation.”  Optimistic and energized, Pentangle’s founders were launching an organization to enrich Woodstock and surrounding communities then and into the future. For a half century, Pentangle Arts has delivered on that vision and more.

Nurturing Appreciation for the Arts

The internationally acclaimed Yale Whiffenpoofs provide a unique experience during Wassail Weekend.

Through these 50 years, Pentangle has consistently brought high-quality arts education programs into area schools, giving thousands of students introductions to and experiences with performing arts, poetry, music, and literature. With concerts, theater, films, exhibitions, workshops, professional mainstage commercial productions, and veteran and emerging artists’ work and debuts, Pentangle has nurtured appreciation and participation in the arts and humanities. From musical comedies to first-run movies and kids’ talent shows, audiences of all ages have enjoyed great entertainment thanks to Pentangle. Along the way, Pentangle spearheaded the 1980s’ massive upgrade and renovation of Woodstock’s Town Hall Theatre.  This fall, Pentangle Arts celebrates its first half century. A festive performance is scheduled for November 23. At this milestone, Pentangle is reflecting on its past and present while also looking ahead.

Deborah Greene EXECUTIVE DIRECTOR

“We want to honor and incorporate the past and open the door to what is next. We are at an inflection point,” says Deborah Greene, Pentangle Arts’ new executive director. Deborah, who grew up going to Pentangle productions and events, took the helm from Alita Wilson this summer. Alita served as Pentangle’s executive director for 10 years—a tenure that included the COVID-19 pandemic and Pentangle’s rebound from it.

How It Started

Pentangle’s history as an organization started with a group of dedicated area residents who got together at the home of Polly and William Billings in 1974. Wishing to expand art opportunities in area schools and the community, they envisioned a nonprofit organization similar to the Vermont Arts Council, but with a local focus. In August 1974, Pentangle organized its first Summer Festival, four days of arts featuring Apple Hill Chamber Music, Canterbury Contra Dance Orchestra, Rag Time Jazz, an exhibition by local artists, and more. That school year, Pentangle had 11 programs in area schools—a mime, marionettes, the Vermont Symphony Youth Concert, and the Arthur Hall Afro-American Dance Ensemble among them.

Through its first years, Pentangle had an office, but no performance venue of its own. In the 1980s, an opportunity emerged for Pentangle to move forward, also connecting to an arts vision for the community dating back to 1899.  Back in 1899, needing an adequate town hall, Woodstock town built a grand new neocolonial building adjacent to the Green. The ample town hall for meetings occupied the first floor. Performing arts were prominent in the town’s vision, so the second floor was home to a glorious 400-seat opera house with proscenium stage, balcony, and stage curtain painted to depict the Bay of Naples. Opened in late 1900, the Opera House was a lively community hub as traveling theater companies, opera, vaudeville, community theater, and speakers on subjects including prohibition graced its stage.  After a 1920s fire extensively damaged the building’s interior, in the renovation, the theater moved to the main floor. The structure also got a facelift, adding its stately front porch and Greek-styled columns. Live entertainment resumed—and motion picture screenings. In 1930, a sound machine for the new “talkies” was installed.

A New Era

Prydein has graced the stage at both summer and holiday events, wowing the crowd with their bagpipe rock sound.

By the 1980s, the theater was in rough shape, and in violation of building and safety codes. Pentangle’s board and Executive Director David McWilliams recognized the desirability of a community performance center and saw that this historic building and theater could again be a showcase for the town. Pentangle launched an ambitious capital campaign raising nearly one million dollars that funded extensive renovations. The Town of Woodstock owns the building and has offices there; Pentangle is steward of the theater.

The Town Hall Theatre opened in late 1987 with a sold-out performance by Canadian composer and jazz pianist Oscar Peterson. A few months later, community members were back on their Town Hall’s stage with the New Woolhouse Players production of Rodgers and Hammerstein’s Oklahoma! directed by Tom Beck. Tom has directed several more musicals there, including The Producers in 2018 and is directing the upcoming 50th anniversary showcase. Selections from those community musicals and much more will be on the program.  Shows in the Town Hall Theatre have run the gamut from large-scale professional traveling productions to small, intimate ones featuring local talent. A multiyear partnership with Artistree brought shows including Cats and Cabaret to the theater. Pentangle Players’ productions included Gilbert and Sullivan’s Pirates of Penzance and The Rocky Horror Show. Along with the big productions, another component of Pentangle is giving local artists a spotlight—a venue for a film or play debut or concert.

Pentangle Today

Music by the River is held each summer at East End Park and hosts national artists such as the Houston Bernard Band.

Pentangle’s Arts in Education Program continues as one of its pillars, enriching lives of thousands of students through performances, artist residencies, after-school programs, and its long-running popular Summer Performing Arts Camp. In the summer, Pentangle’s Music by the River concerts held in East End Park are enduring favorites. Summer 2024 featured six of these free concerts.  Pentangle keeps up a lively movie schedule. Box-office manager Nick Sweetland notes that the screen is still believed to be the largest in the region. First-run movies are screened every week. Throwback Thursdays bring classics to town. The Wild and Scenic Film Festival and the Vermont Film Festival are among recent multiday events hosted there.

Pentangle collaborates with many, many organizations, including the Woodstock Area Chamber of Commerce for festive holiday fare over Wassail Weekend in December, Zack’s Place Enrichment Center for their annual immensely popular musical, and the Vermont Symphony Orchestra on their summer tour.

At this 50-year milestone, Pentangle is looking ahead. Pentangle’s founders’ vision and action have profoundly enriched the community. This fall, Pentangle celebrates that and opens the door on its next decades involving and inspiring the community with high-quality affordable arts from around the corner and around the world.

A Note from the Writer

Pentangle Arts, like other longstanding vibrant organizations in our area, is an enduring success because of the many, many people who have brought inspiration and years of commitment to it. Few names are mentioned here, because, honestly, it would be impossible to acknowledge all of the generous and farsighted individuals who have given this gift of Pentangle Arts to the community.

Pentangle Arts
Woodstock Town Hall Theatre
31 The Green
Woodstock, VT
(802) 457-3981
  pentanglearts.org


Deborah Greene
Executive Director

Deborah Greene, whose ties to Woodstock date back to her childhood and her family’s home here, began her tenure as Pentangle executive director this summer. Founder of Vermont’s TEDxHartlandHill conference at Billings Farm & Museum, Deborah permanently moved back to Woodstock in 2020.

A filmmaker, actor, director, writer, arts administrator, and educator, Deborah is an alumna of Boston College. She earned her master’s degree in Public Administration, Global Diversity Governance from Coventry University. For five years she has been a delegate at the UN Commission on the Status of Women, as well as being a guest speaker at each event.

My favorite thing is to sit in an empty theater and dream. Whether I’m in the audience looking at the stage or on the stage looking at the audience, my eyes get bigger and I get creative and I think and dream about what can be.

“To be here at Pentangle at the moment where we are launching into our next 50 years and I can sit in the theater and dream of what it can be—that is a dream for me.”