New Woodstock Day School head says he’ll be sticking around

After watching several directors of the Woodstock Day School (WDS) come and go over the past few years, parents are looking for stability, said David Penberg, Ph.D., recently installed as the school’s new head. “Turnover in leadership is never a good thing for a community,” he remarked. “The parents want to know, ‘Is he here to stay?’”

After heading a series of schools in New Jersey, New York City, Mexico City, and Barcelona, and most recently consulting as academic advisor to the Misk Foundation in Riyadh, Saudi Arabia, Penberg’s answer to the question is a solid yes. “At this juncture in my life, it’s a time for homesteading — a time to deeply plant roots and grow them with a community over time. The Woodstock Day School is that place”

And after spending a year in Riyadh, among the extremes of the desert, he’s delighted to return to the natural beauty of the Hudson Valley. “I was nature-deprived, in a way, although the desert is in and of itself an ecological wonder,” he said. “After near-Biblical sandstorms, where the sky would turn an ominous black, and living constantly with air conditioning, being in the Catskills is like a sensory epiphany. Everything from the shades of green to the sounds of birds and wind feels like a homecoming. And to have 45 acres of the natural habitat as a campus at WDS — it’s a dream I’ve long waited for.”


Penberg grew up in the Bronx, which he calls New York City’s greenest borough, went to summer camps in the Berkshires, and attended Bard College. He and his wife, artist Janelle Lynch, have split their time between Manhattan’s West Village and a renovated barn in Sullivan County with their golden retriever, Gracie. For now, Penberg is commuting from there.

His life as an educator has been a broad exposure to the full spectrum of learners and learning environments. He has headed independent, international, and charter schools and held leadership positions in community centers (Washington Houses in East Harlem) and community-based programs (The Door). He taught in Pace University’s Teaching Fellows Program, ran Environmental Science Academies with Bank Street College at Bard, and is a contributing writer to The International Educator and Independent Schools Magazine. His collection of essays entitled Deciding to Love the World is forthcoming from Wintergreen Studios Press. 

Last year, Penberg was invited to Riyadh as an academic advisor to help create a new school, “a new paradigm for learning and teaching in Saudi Arabia,” he explained. “It was a once-in-a-lifetime opportunity to be involved in what seemed like writing history. My charge was to write a strategic plan, develop a new model for professional learning, and to cultivate strategic partnerships.”

The experience was exhilarating, transformative, and cross-culturally challenging. “I was stretched in ways I didn’t think I had the muscle tissue,” Penberg said. “At the same time, I had opportunities to develop collaborative relationships with the finest learning organizations in the world: the Smithsonian, Bard, MIT Media Lab, Harvard’s Project Zero, Bank Street College. It reaffirmed and drew on everything I’ve come to know about how you build and grow a dynamic school culture from the ground up.”

Since arriving at WDS on June 28, Penberg has been talking to parents, students, staff, and other community members. When asked if he has a vision for the school, he said, “Right now it’s all about collecting and gathering perspectives of the stakeholders, getting to know the community from the inside out by asking lots of questions, and listening actively. Of course there’s a vision, but it has to take shape, be blended and synthesize with the collective vision of what people care about and value, and how they imagine their school five to ten years from now.”

While he’s gradually absorbing an understanding of the needs and wants of the community, he does bring his own ideas to the table. He’s looking at expanding the school’s profile through the function of what he calls “a convener, bringing diverse organizations and people together locally. What would a consortium of local educating institutions, schools, museums, art centers working together look like? What could they do together that they can’t accomplish alone?”

In Barcelona, he found a way to unite the various international schools, in an effort to get the schools collaborating rather than competing. “It changed the landscape of how we worked together by creating a synergy of collective initiatives. And that is what I am envisaging here. It’s no longer viable or sustainable to operate according to territoriality.”

Penberg would also like to launch a WDS radio station. “I want kids to be advocates and activists of the most pressing issues in their lives. What better way to consolidate WDS strengths in media arts and literary arts than to expand to the radio? Besides, we have some great examples of youth-driven radio documentary to draw on.”

He sees technology as an area that needs attention at the school, and he hopes to create a tech plan to guide movement in that direction. “The nature of the digital world requires that we surround kids with powerful tools to communicate and create in ways that are thoughtful, as well as culturally and developmentally appropriate. The question is: How do you marshal the best opportunities of the digital world while enhancing, not detracting from, community life?”

As for the strengths he sees at WDS, he emphasized “the human resources. I’ve found some extraordinary people with a commitment as educators. Families are deeply invested in the life of the school, beyond the self-interest of their own children. There is an immeasurable level of creativity and volunteerism flourishing in the community. You want to feed that and build on it.”

The campus is also a major resource, especially given that commitment to the environment is among the missions of WDS. He pictures the school’s acreage becoming an ecological hub for research, study, and advocacy, with students as environmental warriors and stewards.

Then there’s the joy he finds palpable at WDS. “It’s something you can’t counterfeit or make up. I strongly believe school should resemble camp life as much as possible.” He paused to listen to the shouts of children outside who were attending the WDS summer camp. “Even in the rain, there is a level of happiness that pervades this place. I want to preserve that as part of the social and emotional wellsprings of WDS culture. With that in place, a school can be become whatever it chooses.”