By Avi Dresner
Each year, as the busy Berkshire summer season winds down and the tourists and part time residents return home, a new group is arriving: boarding school students. Indeed, the region is not only blessed with some of the best public and private cultural institutions in the country, but some of the best educational ones. According to U.S. News & World Report, Massachusetts perennially ranks first in the nation for public schools (with two Berkshire high schools in their top 40—Mount Greylock Regional High School in Williamstown at #25 and Lenox Memorial Middle and High School in Lenox at #37). The Berkshires and neighboring Columbia County, New York, and Litchfield County, Connecticut, are also home to exceptional private day and boarding schools that are the choice for many local, out of-state, and international families.
Private schools allow families to choose the type of education that specifically meets a student’s needs, says Rebekah Jordan of Crossbridge Education Consulting. “The nurturing, advising, and identity building that come from a private school are greater than what you typically get in a public school. You also have the ability to tune your dials much more finely when it comes to curriculum, level of intensity, and rigor and style of teaching,” said Jordan. “Very few public schools can fully embrace a progressive education, for example, where students are given a lot of democratic responsibility and ownership, to help co build the curriculum with their teachers, like one might find at a Waldorf or Montessori school.” And, for some parents, religious education is another important factor.
When it comes to boarding schools, there are additional features that are attractive to some families. Boarding school teaches independence; students learn about your strengths and challenges away from family, and how to live in a dorm environment. Those skills can help prepare teens for success in college.
Beyond these general reasons to attend private school, there are specific advantages to choosing a facility in the Berkshires. “There is literally something for everyone,” Jordan said of the diverse educational offerings. The culture and nature here are a draw not just for students but for faculty—this area is home to some of the most creative and talented people in the country, and private schools dip into that deep pool of talent for faculty and staff. And going to school where there’s easy access to nature allows for areas of study you might not find elsewhere.
With so many schools to consider, choosing the right one can be daunting. (That’s where educational consultants can be helpful.) For day school families, Jordan suggests asking yourself, “Do you have the bandwidth to support this both logistically and financially?” For example, how long a drive is it from home and is it in the same direction you’re already going?
The most important factor by far in choosing the school for your child and family is finding the right fit, and for that there’s no substitute for visiting the school. Just another reason to spend time in the Berkshires.
The following professionals provided advice for this article: Rebekah Jordan of Crossbridge Education Consulting; Vince Schmidt, director of admissions and enrollment management at Darrow School in New Lebanon, New York; and Liz Hodosy, senior associate director of admissions at Indian Mountain School in Lakeville, Connecticut.

How to Stand Out and Get In
5 TIPS FOR APPLICANTS
The process can be stressful—for both kids and parents! We asked the insiders for some advice, and here’s what they said.
1 Be authentic. If an application looks like it’s been done by a professional, that’s a red flag. If a student is trying to be someone that they’re not, it’s not going to feel good once they’re there.
2 When you visit the school, be prepared. Do your research beforehand, and come with questions.
3 It’s not just the child being interviewed. Parents, through the application and interview process, should be mindful that they’re showing what kind of a partner they’re going to be to the school.
4 Do your research. If you work with an educational consultant, look for one who is a member of the Independent Educational Consultants Association.
5 Get involved. Most schools are looking for students who are eager to be a part of and contribute to their community—the tour and interview provide great opportunities to showcase the ways in which you plan to do so.

The Schools
Here are the basic stats to get you started—and a little more about the schools, in their own words.
BERKSHIRE COUNTY
Berkshire Country Day School (Stockbridge)
Grades Pre K–8 | 126 students
Day school
berkshirecountryday.org
“Our intentional approach of inquiry, discovery, and discussion blends proven methods with emerging best practices to draw fully on the experiences and contributions of our entire school community. Our comprehensive curriculum, which includes project-based and experiential learning, leverages the talents of our exemplary educators and the natural resources of our extraordinary campus to inspire independence, academic excellence, and mutual respect.”
Berkshire School (Sheffield)
Grades 9–12 | 400 students
87% boarding
berkshireschool.org
“By design, every student makes an impact at Berkshire. No student is anonymous. Everyone knows everyone—from faculty and staff to new students and graduating seniors. Our enrollment of 400 students is a sweet spot for Berkshire’s model and culture, allowing us to cultivate an exceptionally affirming and close knit residential community. From the foundation of being known well, our students build confidence, which enables them to strive, take risks, and reimagine their potential in all areas of their development.”
Summer visits available Tuesdays, Wednesdays, and Thursdays through August 15.
Berkshire Waldorf School (Great Barrington)
Grades Pre K–8 | 200 students
Day school
berkshirewaldorfschool.org
“Waldorf education was founded in 1919 by scientist and philosopher Rudolf Steiner. Based on Steiner’s insights into the nature of human beings and child development, our Waldorf curriculum fosters each student’s natural curiosity with stories and activities that appeal to the imagination as well as the intellect.”
Berkshire Waldorf High School (Stockbridge)
Grades 9–12 | 50 students
Day school
berkshirewaldorf.com
“Waldorf education is a humanistic approach to pedagogy based upon the educational philosophy of the philosopher Rudolf Steiner. Learning is interdisciplinary, integrating practical, artistic, and conceptual elements. The approach emphasizes the role of the imagination, developing thinking that includes a creative as well as an analytic component.”
Buxton School (Williamstown)
Grades 9–12 | 65 students
90% boarding
buxtonschool.org
“Our mission is to create an environment where truly progressive education can be lived every minute of every day, where learning is personal, meaningful, equitable, and relevant. By doing this, we equip Buxton students and alumni to be deeply reflective and creative builders and shapers of every community they touch.”
Miss Hall’s School (Pittsfield)
Grades 9–12 | 190 students
All girls school | 75% boarding
misshalls.org
“Miss Hall’s has provided, since our founding in 1898, an exceptional academic education and the opportunity to develop values core to the human experience: authenticity, respect, honor, and growth. Our students have, since the beginning, become bold and creative contributors to the common good.”
The Montessori School of the Berkshires (Lenox Dale)
Grades Pre K–8 | 140 students
Day school
berkshiremontessori.org
“Our mission is to prepare children for life. All children are naturally curious and love to learn. We support this innate drive by providing environments that meet children’s developmental needs, by creating a staff of loving and well prepared adults, and by building a community of families that actively support our mission.”
Pine Cobble School (Williamstown)
Grades Pre K–9 | 158 students
Day school
pinecobble.org
“Pine Cobble’s focus is to cultivate in each student a lifelong passion for learning, a strong sense of self-worth, and respect for others throughout the community. Our motto, Nosce Te Ipsum, Know Thyself, represents our belief that the key to a meaningful life is understanding who we are as individuals in relation to others and the world around us.”
St. Agnes Academy (Dalton)
Grades Pre K–8 | 135 students
Day school
saintagnesacademy.com
“St. Agnes Academy is a Catholic parish school, united by God’s love, living and sharing our faith daily. We strive for academic success while promoting awareness and appreciation of community involvement as a lifestyle. Within this secure, welcoming environment, our experienced, dedicated faculty and staff celebrate the uniqueness of each child from pre-school through grade eight.”
St. Mary’s School (Lee)
Grades Pre K–8 | 85 students
Day school
stmaryslee.org
“St. Mary’s School welcomes all children to a small, safe, nurturing environment that fosters a love of learning and keeps Christ in their daily lives. Students are empowered to attain academic excellence while becoming cooperative learners, responsible citizens and dedicated leaders serving others in an ever changing world.”
St. Stanislaus Kostka School (Adams)
Grades Pre K–8 | 85 students
Day school
ststansadams.org
“The mission of our school is to provide quality Catholic education in a safe, loving, and nurturing environment. We work to model for students the values of faith, family, respect and loving service.”

LITCHFIELD COUNTY
Canterbury School (New Milford)
Grades 9–12 | 325 students
70% boarding
cbury.org
“Canterbury is an independent, coeducational boarding and day school for grades 9–12 and postgraduates. Yet, it’s more than a school, more than a place. It’s a promise grounded in our belief in your extraordinary potential.”
The Frederick Gunn School (Washington)
Grades 9–12 | 325 students
78% boarding
frederickgunn.org
“Frederick Gunn was a pioneering educator, courageous abolitionist, and rugged outdoorsman. He inspired generations of students to be curious and thoughtful, to be active members of their communities, and to stand up for what they believe in. He was a transformational leader. Our students become principled, active citizens and lifelong learners who will be entrepreneurial forces for good in the world.”
Forman School (Litchfield)
Grades 9–12 | 210 students
80% boarding
formanschool.org
“At Forman, we embrace students as individuals, both in the classroom and out of it. Our nurturing faculty tailor lessons to adolescents with dyslexia, dysgraphia, dyscalculia, ADHD, and executive function deficits—as well as twice-exceptional students.”
The Hotchkiss School (Lakeville)
Grades 9–12 | 600 students
95% boarding
hotchkiss.org
“The Hotchkiss School is defined by our commitment to fostering excellent, wholly developed learners. We focus on empowering students to become fully prepared for the future beyond. Through small class sizes, a breadth of more than 200 courses, and a teaching dynamic that cultivates academic curiosity, every student graduates ready to become a global citizen and a community leader.”
Summer tours offered Mondays and Fridays from June 24–August 16.
Indian Mountain School (Lakeville)
Grades Pre K–9 | 300 students
40% boarding
indianmountain.org
“The paths taken at IMS are just like the paths up our mountain: different for everyone, rarely in a straight line, and ultimately rewarded with new perspectives, an expansive view, the spirit of possibility, and the tools necessary for the challenges and opportunities ahead.”
Kent School (Kent)
Grades 9–12 | 520 students
93% boarding
kent-school.edu
“We are guided by our motto—Simplicity of Life, Directness of Purpose, Self-Reliance—to educate our students intellectually, socially, ethically, and spiritually so that they will be prepared to contribute to the common good in the world beyond Kent School.”
Marvelwood School (Kent)
Grades 9–12 | 120 students
80% boarding
marvelwood.org
“Our School takes pride in the purposeful planning of academic, extracurricular, residential, and social initiatives that promote open communication, foster meaningful relationships, and provide a true sense of belonging.”
Rumsey Hall School (Washington)
Grades K–9 | 321 students
38% boarding
rumseyhall.org
“Rumsey Hall School is committed to a whole-child approach to education and believes that teaching academics and teaching an attitude of mind are of equal importance. The School emphasizes effort as a criterion for success and is dedicated to helping each child develop toward his or her maximum stature as an educated person, a successful member of a family, and a contributing member of a community.”
Salisbury School (Salisbury)
Grades 9–12 | 310 students
All boys school | 93% boarding
salisburyschool.org
“At Salisbury we do everything right for boys! We celebrate what it means to be a boy and have designed a school where boys succeed and tradition matters. Our unique Hilltop community develops boys into gentlemen both in the classroom and out. As a student at Salisbury, you are part of a close-knit community. From the moment you first arrive to the day you graduate, you play an important role in the life of the School.”
South Kent School (South Kent)
Grades 9–12 | 150 students
All boys school | 97% boarding
southkentschool.org
“Guided by 100 years of academic, athletic, and student traditions, we work together to develop thriving young men. Using our contemporary expertise in male adolescent education, we are constantly evolving and adapting to ensure we are providing students with the skills and developing the character they will need to succeed in college and the world beyond.”
The Taft School (Watertown)
Grades 9–12 | 580 students
82% boarding
taftschool.org
“More than 125 years have passed since Mr. Taft founded our school. While the world and the school have changed dramatically, his fundamental values endure: work hard, without regard for public acclaim; develop all of your talents, academic, artistic, and athletic; and most important, give of yourself to others.”
Torrington Christian Academy (Torrington)
Grades K–12 | 215 students
Day school
tcact.org
“We are deeply committed to our community, investing in one family at a time as we partner with parents to help children achieve their greatest potential. Our highly qualified educators come from a variety of denominational backgrounds but are unified by one common goal: creating a safe place where your child is well-loved and well-instructed.”
The Woodhall School (Bethlehem)
Grades 9–12 | 45 students
All boys school | 100% boarding
woodhallschool.org
“The mission of The Woodhall School is to provide an opportunity for success to young men of above average intellectual ability in grades 9-12, who have had difficulties in traditional school environments. The school embraces an individualized approach that allows each student to realize his potential and to take accountability in all areas of his life.”

COLUMBIA COUNTY
Darrow School (New Lebanon)
Grades 9–12 | 110 students
85% boarding
darrowschool.org
“Darrow School is dedicated to serving students with diverse backgrounds and abilities, building on each student’s individual talents and interests to inspire enduring confidence for success in college and life. This mission is accomplished through our curriculum, which is rooted in the liberal arts and sciences, individually focused, and combines innovative classroom instruction with project-based learning and environmental consciousness.”
Hawthorne Valley Waldorf School (Ghent)
Grades K–12 | 308 students
Day school
school.hawthornevalley.org
“Our school’s location on an organic/biodynamic farm supplements the curriculum by providing our students with the opportunity to develop connection to the natural world, and a love of outdoor adventure.”

The College Years
When it comes to higher education, there are local choices for every type of student.
Bard College (Annandale-on-Hudson, NY)
1,800 students
bard.edu
“Bard College seeks to inspire curiosity, a love of learning, idealism, and a commitment to the link between higher education and civic participation. The undergraduate curriculum is designed to address central, enduring questions facing succeeding generations of students.”
Bard College at Simon’s Rock (Great Barrington)
400 students, average age of entering student is 16
simons-rock.edu
“Simon’s Rock is the best choice for students ready to make a deliberate break with the standard educational track. No one comes to Simon’s Rock because it’s what their parents expect them to do—or what all their friends are doing. If you’re determined to find an unabashedly intellectual, proudly independent, fiercely creative college community as soon as possible, no other option comes close.”
Berkshire Community College (Pittsfield)
2,000 students
berkshirecc.edu
“Berkshire Community College is committed to providing an exceptional education and a wide range of opportunities that meet the diverse needs of our community through college transfer, workforce and career pathways, partnerships and lifelong learning.”
Massachusetts College of Liberal Arts (MCLA) (North Adams)
1,050 students
mcla.edu
“We’re the public liberal arts college in Massachusetts. In every way possible, the experience at MCLA is designed to elevate you as an individual, a leader, and a communicator, fully empowered to make your impression on the world.”
Williams College (Williamstown)
2,200 students
williams.edu
“Established in 1793 with funds bequeathed by Colonel Ephraim Williams, the college is private, residential, and liberal arts, with graduate programs in the history of art and in development economics.”

