Woodside Montessori Academy

Prospective parents: please look at the numbers before you enroll.
My biggest advice to parents considering Woodside Montessori Academy in Millis is simple: don't make your decision based only on the school tour or the Montessori philosophy. Ask questions, look at the numbers, check the public records, and talk to families who have actually experienced the school.
Start with three very simple questions
When you tour the school, ask:
• How many students are currently in Lower Elementary?
• How many students are currently in Upper Elementary?
• How many students are currently in Middle School?
Then ask the most important follow-up question:
How many students who enter the elementary program actually stay through Middle School?
In my experience, the school appears to lose a substantial percentage of its students as they move into the higher grades—around 50 by my observation. Prospective parents should verify this for themselves and ask the school for its actual student-retention numbers.
Don't just ask how many students are in each classroom today. Ask how many students stay from elementary through Middle School.
Ask about teacher turnover
I would also ask:
• How many teachers have left during the past five years?
• How long have the current Lower Elementary, Upper Elementary, and Middle School teachers been at the school?
• What is the teacher turnover rate?
• How many students are assigned to each teacher at each level?
Teacher stability matters, especially when you are considering a school for many years.
Check the EEC records
I also recommend that prospective parents check the school's EEC records before enrolling.
The school has been operating since 1985, and parents should look at its inspection, monitoring, and investigation history themselves.
The EEC public record shows multiple monitoring visits and also lists an investigation in 2025 in which non-compliances were identified.
The school never shared this 2025 investigation with parents. We were kept in the dark about what happened, what the non-compliances were, and what corrective actions were taken. Parents should ask the school directly for an explanation and review the public EEC records themselves.
I'm not suggesting that parents take my word for it. Look at the EEC records yourself and ask the school to explain anything you don't understand.
Parents should also ask about the school's current accreditation status and any accreditation it is pursuing.
PE and facilities
The PE program is another concern for me.
The school does not have a dedicated PE facility. Students have had to run around the school's backyard along the fence for PE, and for some activities the school has to use facilities elsewhere.
The school has also used the front yard of a nearby church for student PE activities. In our experience, some students developed poison ivy exposure/rashes after being in that area.
Parents should ask exactly where PE takes place, what facilities students have access to, and what arrangements the school has for physical education.
There is also no dedicated music teacher. If music education is important to your family, ask exactly what music instruction your child will receive and who provides it.
The school also does not have a dedicated room or auditorium for plays and large performances. For school plays, the school has to rent a large room from a local church, so students and parents have to leave the school campus to attend these performances. Prospective parents may want to ask how often outside facilities are rented and what the school provides for performances and other large school events.
The approximately $1,000 activity fee
The activity fee is around $1,000 per child.
That is a substantial amount of money when multiplied by the number of students.
Parents have asked reasonable questions about how this money is spent. How much goes toward each field trip? How much goes toward other activities? How much remains?
In my experience, we did not receive the detailed accounting we were asking for.
I am not accusing anyone of financial misconduct. My concern is transparency. If families are paying around $1,000 per child, I believe it is reasonable for parents to want a clear explanation of what the fee covers.
Ask for the details yourself.
Ask where graduates go
Parents should also ask where Middle School graduates actually go after Woodside.
From what I have observed, many Middle School students who continue to high school attend Tri-County Regional Vocational Technical High School.
There is nothing wrong with choosing a vocational high school. The important thing is for prospective parents to understand the typical path of Woodside graduates and ask for actual graduate-placement information.
Talk to families who left
If you are seriously considering Woodside, don't speak only with the families the school recommends. Talk to current and former parents and ask about their actual experiences. Do your

This school has made such a change in our children's lives- the teachers, the staff, the Montessori method of honoring children while preparing them so well academically... We are so thrilled. My children are younger, but I can tell you that the middle schoolers will be graduating with not only very strong academics but much more worldly experience and community enrichment experience than the average child their age. Woodside sets kids up on a course to both do well for themselves, and to be kind and productive members of the local and world community. Investing in the early years of education is the best gift you could give your child. Private high school may give your kids a leg up- but excellent elementary education gives them wings!

We are very impressed with our experience with our 2 children at Woodside Montessori Academy. My daughter is in second year preschool and it is just incredible to see what her class is learning. She has studied and is exposed to so much more than any preschool program I have seen. They cover the basics, but also have geography, science, astronomy,and Spanish to name a few. The 3 year age grouping allows for peer collaboration, which has proved to be great for my daughter. The teachers are wonderful and the environment is warm and supportive. This school is an excellent choice!

We are so satisified with our decision to place our children at Woodside Montessori Academy. The kids are exposed to such a great variety of subject matter that they would not typically be learning in a public elementary school, especially not at their grade level. For example, our first grader is already learning about astronomy, geometry, geology, geography, and more! This is accomplished all while still following the Massachusetts required curriculum. We highly recommend this school!