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A supportive & caring community


Meet Our


Leah Shapiro
Residential Leader

Lisa Howard
Residential Leader

Pursuing Interests

Student Life

John Dewey students learn how to gain healthy control of their lives in an environment that promotes self-respect and respect for others. The daily schedule provides a basic structure, yet also encourages the development of time management skills in order to meet the demands of a challenging curriculum. Students attend classes, study regularly, participate in groups, complete household responsibilities, engage in physical exercise, and interact with their peers. When their schedules allow, they also pursue other areas of interest such as art, music, sports, gardening, and volunteer work.

A Rewarding Environment

Daily Life

Learning to manage daily life is a personalized and very real marker of growth for our students. They attend classes for much of the school day, though our model is more similar to a college schedule than that of a typical high school. Between classes, they study or fulfill their responsibilities around the house. They also prepare and serve the lunch and dinner meals. Students gather for community meetings and therapy groups 3x/week. In the evenings, students prepare for their classes (either individually or in small groups) during a quiet study hall from 7 until 9 p.m. Every night there is a peer-led Night Group.

During free time, students may read, work on homework, socialize with their peers or staff, go to town to visit the coffee shop, public library, do errands, play piano or their instrument, take a walk outside, bake cookies, read the newspaper, go to a dance class, or fulfill various chore responsibilities around the school or grounds.

Friends and Fun

Weekend Life

After a Saturday morning study hall, students fulfill academic and personal responsibilities or engage in recreational activities. They may go into town for movies, shopping, and meals. Weekend and break activities, often initiated and planned by students, are approved by the Dean of Students and facilitated by the house parents.

Building Character

Responsibilities & Leadership

With the guidance and supervision of the staff, students help run the John Dewey Academy. We empower students to take ownership of their lives and their community in order to facilitate the development of integrity and moral leadership.

Students undertake responsibility for the maintenance and management of the school, including planning menus, ordering food, cooking, maintaining the grounds, planning community outings, helping the business manager with administrative tasks, and cleaning the building. Working in teams, they learn to address real-world tasks in a disciplined way. As they rise to positions in which they must render their opinions, act decisively, and delegate responsibilities, they develop strong leadership abilities. Student leaders manage the day-to-day duties of the business, academic advising, housekeeping, kitchen, and maintenance teams and also serve as academic advisers and tutors. Students play an active role in formulating and implementing school policies. Although the Head of School retains the right to make the final determination, he remains accountable to the students, staff, and parents.

Enriching Daily Life

Extracurricular Opportunities & Clubs

We encourage students to pursue their passions and interests through a variety of extracurricular activities and student-initiated clubs. In the past, students have:

  • Started a variety of clubs: Magazine, Fashion, Economics/Investment, Cinematography, Gardening, Photography, Chess, and Weight Lifting
  • Mentored children in the Big Brothers Big Sisters volunteer program
  • Volunteered with a local environmental organization (Greenagers)
  • Volunteered at various community events
  • Participated in writing competitions and workshops such as The New England Young Writers Workshop (“Bread Loaf”), Poetry Out Loud, and local poetry “slams”
  • Entered art, music, and academic competitions
  • Created and maintained a community garden
  • Interned with a federal judge
  • Hosted a weekly music program on a local radio station
  • Interned with a local newspaper
  • Interned with the Town Hall
  • Participated in Model UN
Individual Discovery

Sexuality, Health & Wellness and Diversity

We believe in nurturing the development of the whole child, and to that end, we provide programming to address issues of sexuality, health, nutrition, wellness, and diversity. These may be stand-alone classes, seminars, groups, or community lectures. In some cases, this educational material is woven throughout academic classes. Some examples include: weekly yoga and sitting meditation, a mindfulness-based wellness course, sexuality and sex education seminars; and psychoeducational groups, classes, or lectures on racial inequalities, gender stereotypes, economic inequalities, sexual and gender identity, etc

Health & Wellness


As a destination resort, the Berkshires region offers multiple cultural and recreational opportunities, including classical music, theater, dance, museums, and lectures. We are in close proximity to a variety of well-known cultural destinations including: Tanglewood, Jacob’s Pillow, Shakespeare & Co., Chesterwood, Berkshire Theater, Mass MOCA, Barrington Stage Company, and the homes of Edith Wharton and Herman Melville, to name a few. During the summer, students can hike, swim, and camp; in the winter, ski slopes are only three miles away.

Because the John Dewey Academy is a small school, we do not have organized sports teams. However, when there is interest, students often organize basketball and soccer games, tennis matches, ultimate frisbee, and long runs or biking excursions around town. There are opportunities to play sports in the community and against other small high school teams in the area. We encourage students to maintain a regular exercise schedule which can consist of a variety of enjoyable activities including: hiking, biking, running, skiing, swimming, weight lifting, dance, yoga, pilates, etc.

Get In Touch

Contact Us


    389 Main Street
    Great Barrington MA 01230


    Admissions: (413) 528-0084
    General: (413) 528-9800
    Fax: (413) 528-5662

    Email: Info@jda.org

    Leah Shapiro

    Residential Leader 

    Leah joined the John Dewey Academy in 2020. She is currently pursuing an M.S.Ed. in international educational development at the University of Pennsylvania. Prior to starting her master’s program, Leah worked with higher education and youth development programs in the U.S. and abroad. Her most recent position was assistant director of international student services at The College of Saint Rose in Albany, New York. Leah’s professional background also includes leading high school students on an outdoor adventure program in Mongolia, teaching English on a Fulbright grant in Georgia (country), and organizing educational trips across the U.S. for international military officers with the U.S. Department of Defense. 

    When she’s not daydreaming about her next international trip, Leah loves hiking, paddling, and experimenting in the kitchen.

    Lisa Howard

    Residential Leader

    Lisa joined Dewey in July, 2020 as a Residential Leader. She earned her BA in Liberal Studies at West Chester University and later completed a Special Education Certification at Immaculata University. She went on to earn a Master’s in Adventure Education at Plymouth State University.

    The seamless integration of Lisa’s background experiences, professional expertise and nurturing personality make her the ideal house parent for Dewey students. Growing up on a dairy farm in Lancaster, Pennsylvania, a reverence for hard work, self-reliance and the natural environment is deeply ingrained. Beginning as a Special Education teacher, Lisa worked with students of all ages and an array of academic challenges, including: learning disabilities, behavioral and mental health issues. After almost a decade in the classroom, Lisa shifted her career towards Adventure Education. Traveling around the world, Lisa was responsible for corporate team-building and training teachers how to employ Project Adventure’s Experiential Learning methodologies, its applications for both in-classroom and on challenge courses.

    Lisa continues to work independently as a consultant/facilitator in the team and leadership development fields. Currently she is expanding her life coaching network through a collective she has formed with two colleagues. The new organization, Skillful Warriors, aims to create spaces in which individuals can find connection, support, inspiration and growth through coaching, online courses and events.

    Lisa is unrelentingly dedicated to the philosophy that “in order to create peace around us, we must first be at peace within ourselves.” Her ongoing work with the Skillful Warriors, study/practice of yoga, mindfulness and mediation are just some of the ways in which she consistently strives to cultivate her own inner peace and support others on that same journey. Over and above being a steady, supportive presence for our students, Lisa thoroughly enjoys interactive connections with them. She typically engages JDA students through conversation along with her favorite hobbies: walking, yoga, games and gardening.

    A Sample Day at Dewey:

    7:30 Wake up, breakfast

    8:00 Chores

    8:15 Classes begin

    12:00 Lunch

    12:45-1:30 Class

    1:30  Free time

    2:15-2:30 Community Meeting

    2:30-4:00  Group (M,W,F)

    4:00  Free time

    5:15  Cooking team responsibility

    6:00 Dinner

    7:00-9:00 Study Hall

    9:00-10:00 Student Night Group

    10:00 Free time

    11:00 Bedtime