Jessica Howard
Founding Teacher

I was born in 1942 in Los Angeles, California, and brought up there by my mother and grandmother – after whom I was named. As a child I made up lots of plays, read a lot, and made ‘hide-outs’ with my friends. I decided to be a teacher when I was eleven years old. I spent my adolescent years reading and looking after very young children.

I came to Bennington College after high school. I loved New England, and only later discovered that my father’s family came from New England. I instantly – as a first month freshman – I identified Philosophy as a major. (I also continued to know I would teach.) My other major was history, but I did a lot of math. During the off campus work periods I programmed for computers, worked in a hospital, worked for a sociologist on a psychiatric ward, and worked in a department store. I worked as a camp counselor for six years. After I graduated, I went to Bank Street College of Education, became certified to teach, and taught, first in New York City and then in North Bennington at the then beginning Prospect School. I was associated with the Prospect School from 1966 to 1991. It would take too long to put into words what I learned there – essentially to be who I am, to say nothing of teaching. I left Prospect briefly in 1969 to teach for a year in New Hampshire, and then to study at the University of Connecticut, earning a Master’s degree in Learning Disabilities. I have one son, Asa Keefe. I have lived in my current home in Shaftsbury, VT for 25 years where I discovered my other vocation – gardening. Anybody who wants to talk gardens, just come on by. When Prospect closed in June of 1991, a group of interested parents and teachers joined to begin the Hiland Hall School. Starting and carrying on the school has been a wonderful experience. It’s fun to see how what one has learned can really be put to use.

Why do I teach? I find the way children think, talk, make and do to be endlessly interesting. I love the sense of relationship and discovery;

I love participating in the sense of importance and meaning that children bring to their lives. I just love them.

Quena Crain
Elementary Group Teacher

I grew up on a family ranch in East County San Diego along with my parents, grandparents, and two pairs of aunts, uncles, and cousins. As an extended family we shared one garden, two orchards, four horses, three kitchens, and weekly Sunday dinners. My mother spoke only Spanish to me, and so I grew up bilingual, although I learned to read and write in Spanish first. Literature and writing emerged as my passion as I moved through school, leading me to graduate with a double major in English and Spanish Language and Literature from the University of California, Davis. During my undergraduate years,

I lived in Costa Rica for a year studying literature and elementary school education at the University of Costa Rica, as well as exploring Nicaragua, Panama, Brazil and Ecuador.
After graduating from UC Davis, I moved to Penobscot, Maine to live with my cousin for a year, where my thirsty soul fell completely in love with the lush green of New England, complete with rivers, ponds, and four amazing seasons. In keeping with my love for world-wide education, I worked for several years at World Learning in Brattleboro, Vermont, helping students from the United States travel abroad, and facilitating youth leadership programs for international students. Working with youth programs made me realize I wanted to dedicate myself to the growth of young people full time, so I spent two years in New York City earning my Masters in Teaching English to Speakers of Other Languages (TESOL) and K-12 teaching credential at the Teachers College, Columbia University.

I am very excited about my work and joining the vibrant learning community at Hiland Hall. Music, dance, and exploration of the outdoors are key among my interests and I look forward to incorporating my own passions, along with those of my students, into my teaching.

Brennan Cofiell
Middle School Teacher

Brennan holds a Masters in Teaching for Social Justice from Marlboro College in Vermont. Before settling into the classroom, he earned a J.D. from California Western School of Law in San Diego and is a licensed attorney by the State Bar of California. While pursuing legal work in Southern California, Brennan worked extensively in youth development with a focus on education, adventure, and empowerment. His teaching philosophy is borrowed from Frederick Douglass, who preferred “to build strong children, than repair broken men” and with that in mind, he left a criminal defense trajectory for Social Studies classrooms in his native New England. Brennan speaks three languages, has resided on four continents and loves living in the Green Mountain National Forest. When not teaching in the classroom, you can find him snowboarding, mountain biking, and kayaking in the mountains and rivers of Southern Vermont. 



Meg Cottam

After the closing of the Prospect School, where I worked as assistant to the director, I was invited to sit on Hiland Hall School’s first board of directors. A few years later, as my children became school aged, I enrolled them as students. This was the beginning of a long participation in the Hiland Hall School community - greater and lesser as children grew and moved to other schools. During this time I worked locally and nationally as an artist and educator. More recently, I have offered independent services to individuals and organizations in office management, grant writing and long range planning.
Organizational structures, non-profit management, sustainable systems and working with groups are an enduring interest. The core values and assumptions that attracted me to the Hiland Hall School remain vital. In my current role as director, I strive to support and help implement basic tenets of the school while working with staff, families, children and the community at large.



(802) 442-3868


2196 Harwood Hill Rd, Bennington, VT 05201, USA

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