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Oakes's Corner

Chris Overbye joins the Hunnewell Education Group
as Senior Partner

By Oakes Hunnewell, Ed.M., CEP

I am very pleased to announce the addition of Chris Overbye to the Hunnewell Education Group. Chris brings a wealth of knowledge and experience to HEG. Having grown up, attended and worked at various independent schools across New England, Chris has developed a keen eye when it comes to understanding the differences between them. Chris will be working with students interested in attending day schools and boarding schools locally and nationally. He will also be instrumental in promoting American education as Hunnewell Education Group embarks on a new and exciting journey to introduce international students to US schools, colleges and universities. Please enjoy reading Chris’s biography followed by a short interview.


Chris Overbye joined the Hunnewell Education Group in the fall of 2010 after having spent the past 20 years as a teacher and administrator at several leading independent day and boarding schools across New England. Before joining Hunnewell Education Group, Chris worked as Director of Admissions at Dexter and Southfield Schools managing the expansion of the K-12 enrollment and also served as Director of Admissions at Lawrence Academy and the Indian Mountain School.

In addition to his admission's experience, Chris has served as Director of Development at the Meadowbrook School and at his alma mater, Salisbury School. Chris has enjoyed interacting with students, faculty and parents as an English teacher, a dorm parent, a student advisor and a basketball, baseball and golf coach at Lawrence Academy, Indian Mountain School and the Dexter and Southfield Schools.

As a lifelong advocate for private elementary and secondary boarding schools, Chris brings a wealth of personal and professional knowledge and understands the complexities of both domestic and international applications. "Matching the strengths and talents of applicants to the right day or boarding school is critical to the success of each student. Setting goals for each applicant and understanding the unique educational opportunities available at each school is essential to the placement process."

After attending Indian Mountain School and Salisbury School, he earned a degree from Allegheny College and is currently completing his MLS at Wesleyan University. Chris and his wife Leslie, who teaches at the Fay School, live in the greater Boston area with their 4-year-old daughter Mia.

Some Questions for Chris

Why did you choose a career in education?

I grew up at a school. I was brought up on a boarding school campus. I was fortunate enough to attend both Indian Mountain and Salisbury Schools. After graduating from college as an English major, I explored different careers such as advertising in New York City. What brought me back to education was the opportunity to make a difference in kids’ lives. There were a few teachers who made a huge impact on me and who were strong role models throughout my educational career. As a result, I felt a personal connection to the faculty and also felt like I could have the same impact on others.

What has continued to draw you to the independent school world?

I have had over twenty years of both personal and professional experience in the private school world and clearly see the benefits. Independent schools allow kids to explore their own talents, take risks in the classroom as well as outside and provide the foundation for future success. I really believe in the mission of most independent schools.

Why did you choose to leave schools and become an independent education consultant?

I wanted the opportunity to work independently with families on identifying the right school choice and match. I wanted to use the experience I gained through the years as a director of admissions to promote the right school to the right student. I also wanted to explore the entrepreneurial side of education. Much of education is institutional which has its benefits, but the opportunity to be on my own and to work with a partner to build something we both believe in and to use the network of contacts that I have developed through the years was enticing.

Chris Overbye may be contacted by email at or by phone at 978-807-4420.

School of the Month

Masters School, Dobbs Ferry, NY-


In October, I had the good fortune of visiting the Masters School in Dobbs Ferry, NY. The Masters School is a co-educational boarding school which also includes a middle school. It is situated along the Hudson River just north of New York City. As I arrived on campus, I was immediately struck by the architecture. The school was built on an old estate and has been adding buildings ever since. As a result, the architecture is diverse, reflecting different decades going as far back as the turn of the last century.

What separates Masters from most other boarding schools is its location. Few other boarding schools can boast that they are at the doorstep of New York City. Even more unique is the school’s relationship with the city. Students are encouraged to go into the city and to take advantage of what it offers. Faculty members include the city in their curriculum, often requiring their students to explore it for an assignment or activity. Through programs such as Big Apple Academics, faculty members have developed curricular activities centered on resources found in the city.

In addition to its location, another unique feature of Masters is its student body. Masters nurtures independent and creative thought above all else. Students are encouraged to explore. The Harkness method is employed in all classes including sciences labs. As a result, students at Masters are free to express themselves however they want and feel safe doing so. Though Masters is a discussion based school steeped in the arts and humanities, the school has recently built new science labs. Athletics are viewed as a way for students to express themselves without the pressures of being part of a team with a winning record. A perfect example of this is that the music department shares the same building as the gymnasium.

For more information about The Masters School, please call the admissions office at 914-479-6400.