I Grew Up in Dover. Here’s What Made the Dover-Sherborn Schools So Special.
I moved to Dover in first grade and attended Chickering School. From there, I went to Caryl School for grades four through six — what is now the Dover Community Center — and then on to Dover-Sherborn Junior High and High School.
When people ask me about the Dover-Sherborn schools today, it's easy to talk about academics, class sizes and reputation.
But having actually grown up here, I think there's a much bigger story.
What I remember most is the opportunity.
Small Schools. A Lot of Opportunity.
One of the things I appreciated most about Dover-Sherborn was the opportunity to get involved.
I played varsity soccer, skiing and golf. I was in the band. I played saxophone, flute and oboe. I participated in chorus.
In a much larger school system, I'm not sure I would have had the opportunity — or maybe even the confidence — to do all of those things.
At Dover-Sherborn, you could.
That's one of the things I think people considering a move to Dover or Sherborn don't completely understand until they're here. Dover and Sherborn are both very small towns. Even when the two communities come together for the regional middle and high schools, the school community still feels small and connected.
Teachers know their students. Coaches know their players. Parents know other parents. And kids have opportunities to participate in different sports, clubs, music programs and activities without necessarily having to choose one identity at an early age.
Dover-Sherborn was small enough that you could participate in almost everything, but the experiences available to us could be surprisingly big.
From Dover-Sherborn to a Boston Concert Stage
Being part of a small school didn't mean our experiences were small. Quite the opposite.
One of my favorite examples came through our music program.
Our choral director had connections within the Boston music scene, and somehow that resulted in a group of us getting an opportunity I'll never forget.
This was the mid-1990s. We were high school kids from two tiny Massachusetts towns, and suddenly we were performing onstage at a major Boston concert.
That's a pretty remarkable opportunity for a high school student.
And it wasn't the only experience that took us well beyond Dover and Sherborn.
Sometimes the Classroom Extended Across the Atlantic
There were overseas opportunities as well.
Our language teachers took us to Val d'Isère, France, for an incredible ski and snowboard trip.
Obviously, the skiing was amazing. But the experience was about much more than skiing.
We were exposed to another culture, heard and used another language, experienced a completely different lifestyle and got to see a part of the world many of us had never experienced before.
Those experiences expanded our world while we were growing up in a very small one.
Looking back, experiences like that were an important part of our education too.
Everybody Knew Everybody
There was another part of growing up here that probably sounds almost impossible to kids today.
The parents were connected. Very connected.
We even had a name for their unofficial intelligence network.
This was long before group texts, social media and location sharing. Parents simply talked to one another.
And somehow they always seemed to know what we were doing.
As teenagers, we weren't exactly enthusiastic about this arrangement.
Looking back at it now as a parent myself, I see it completely differently.
They were looking out for us.
Dover and Sherborn were small enough that there was a genuine sense that the adults in the community weren't only watching out for their own kids. People knew one another, families knew one another, and there was a larger network surrounding all of us.
There was accountability, but there was also security in that.
That's the Part a School Ranking Can't Measure
Academics matter. Access to advanced coursework matters. Class size matters. College preparation matters.
But there are parts of growing up somewhere that can't be captured in a ranking or spreadsheet.
I was reminded of that recently when I attended my 30th high school reunion.
The attendance at our reunions has always been extraordinary. And after 30 years, something happened that I don't think any ranking can quantify.
We picked up almost exactly where we left off.
People who hadn't seen one another in years were immediately talking, laughing and reconnecting as if very little time had passed.
That's when it really struck me.
The education and opportunities we received were tremendous. But perhaps the most valuable thing Dover-Sherborn gave many of us was connection.
Chickering to Dover-Sherborn Today
For families considering Dover today, the path looks somewhat different from the one I followed.
Caryl School is no longer an elementary school; the building is now the Dover Community Center. Today's Dover students begin at Chickering School before continuing into the regional Dover-Sherborn Middle School and Dover-Sherborn High School.
The buildings, programs and opportunities have evolved since I was a student.
But the characteristic that made the experience so valuable to me remains fundamental to understanding this community:
It's small. And small can be incredibly powerful.
A smaller community can mean more opportunities to participate, closer relationships with teachers and coaches, and a greater likelihood that somebody notices when a student needs help — or when they have a talent that deserves to be encouraged.
What I Tell Families Considering Dover
I sell real estate throughout Dover-Sherborn, Medfield, Needham, Wellesley, Westwood and the surrounding communities, and they're all great places for different reasons.
But when someone asks me what makes Dover-Sherborn different, I don't start with a ranking.
I tell them what it was like to grow up here.
Chickering and Caryl — Small schools where teachers, families and kids knew one another.
Athletics and music — I could play three varsity sports while also playing multiple instruments and participating in chorus.
Barry Manilow at Harborlights — A high school chorus from two little towns somehow ended up singing backup at a major Boston concert.
Val d'Isère, France — An opportunity to travel internationally, ski, experience another culture and see a completely different way of life.
S.M.U.T. — The parent network we complained about as teenagers and appreciate a lot more as adults.
Thirty years later — Walking into our reunion and realizing that these people still felt like family.
Because that's the part that's difficult to communicate through statistics.
Dover-Sherborn gave us access to an incredible education and some extraordinary opportunities.
But the people and the connections we made may have been the best part of all.
We grew up in two small towns. But the education, experiences and relationships were anything but small.
