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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.

Peg Howes

Part Time Teacher

I grew up outside of Detroit, MI, but have deep family roots in New England. My mom grew up in Vermont’s Northeast Kingdom and my dad’s family came from Keene, NH. As a Bennington College student, I thought I would be an anthropologist and spent time with indigenous people in the Andes of Colombia and Ecuador. I decided this was not my path, but the anthropologist’s skills of observation served me well in my life as a teacher. 

My first serious adult job was as director of an adult education program in Bennington, VT. With no prior experience in teaching or being an administrator, I learned a lot about both through hard experience. One day a friend persuaded me to take a graduate course at Prospect School Center for Teaching and Learning. This was a watershed moment in my life.

At Prospect I discovered new (to me) ways of thinking and looking at the world and people, and a new interest in working with children. I completed a graduate program through The Prospect Center and Lesley College Graduate School while also working on Prospect’s Children’s Archive Project. My first teaching job was a 5th grade class in Dorset Vermont, followed by 2 years as Prospect’s Middle School teacher. I was a reading teacher in Sunderland for several years, then worked in the public elementary school in Stillwater NY for 22 years where I was mostly a third grade teacher. I retired in 2018. Teaching in public schools was a conscious choice. I wanted to bring a progressive education stance into those classrooms.

Along the way I also worked with professional educators teaching observation and descriptive processes in professional development programs. The work focused on ways for teachers to reflect on their own classroom practice and to document children’s learning through classroom observation  and collections of child work. Another focus was ways teachers could support each other and work collaboratively These are useful ideas and practices for teachers who want to be more child-centered, and who are interested in exploring a range of ways to think about assessment.  

I taught in graduate-level summer institutes in Vermont, North Dakota and New York, presented professional development programs for school districts in Vermont and New York State, and served as a facilitator for education organization conferences in New York, Vermont and Maine. 

I am delighted to be joining the Hiland Hall learning community. It feels a bit like coming home. 

Drew Kelly

I grew up in Ashland, Massachusetts, with three brothers close in age.  We lived on a sleepy street in a neighborhood full of kids. Our time was spent on our bikes, in the woods, and running various small businesses (lemonade stands, shoveling snow and other chores).  I studied Business Administration and Human Resources at Northeastern University, with all the psychology & sociology courses I could fit in. After college, I embarked on a career in HR and the corporate world, working in leading Massachusetts businesses in banking and high-tech.


In 1999, an enticing job opportunity led me to the scenic landscapes of Williamstown, MA, where we live today.  Despite the company's eventual move back to Waltham, Ma, I decided to stay, having grown to appreciate the streams, mountains, and a more relaxed way of life in the Berkshires. In the early 2000’s, I co-founded a small publishing company, working with state fish & wildlife agencies.  Over the next 15 years, I focused on growing that company.  After selling that business, I started a couple of other small ventures.


My first encounter with the Hiland Hall School was as a parent when our daughter, Elizabeth,became a student in 2015. The school's unique philosophy and approach to education resonated deeply with me, and I have since enjoyed being part of this community in various roles, from a parent to a board member, and board chair. I’ve been continually inspired, impressed and awed by the students, amazing teachers, the commitment of the board and sub-committees and all the family involvement creating a real community.  


I enjoy spending most of my time with my wife Sheri & our daughter Elizabeth.  For relaxation, I like to cook, sometimes bake and very occasionally painting.  I’ve enjoyed fly-fishing locally over the years, and it still catches my interest from time to time.    


As the Director of the school, I’m committed to supporting the schools mission, and working to support the vision of the board and teachers.  Hiland Hall is now in its 32nd year, with deep and meaningful roots in progressive education.  I can’t say enough about our school, the teachers, board of directors and family group.  In my role as director, I strive to support and help implement the basic tenets of the school while working with staff, families, children and the community at large.

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