Updated September 23rd, 2026
Middle school is the stretch where children change fastest, and it is the point where many families start looking at independent schools for the first time. If you are weighing options in Maryland, here is what actually matters, what these schools cost, and the questions worth asking on every visit.
Start with the size of the class, not the size of the school
The single biggest difference between a public middle school and an independent one is how many children are in the room. A Maryland public middle school class often runs to the high twenties. Independent schools generally run between twelve and eighteen.
That difference decides how much a teacher can notice. Whether a quiet child gets drawn into a discussion, whether a struggle with fractions is caught in October rather than at report card time, whether a child who is ready to move faster is allowed to.
When you visit a school, ask for the average class size in the grade your child would enter rather than the school-wide student-to-teacher ratio. The ratio counts every adult in the building. The class size is what your child experiences.
At Kent School, middle school classes average about 15 students, with an 8 to 1 student-to-teacher ratio across the school.
Ask where the students go afterward
A middle school's real work shows up two years after a student leaves it. Ask every school you visit where their eighth graders went, and how the school supported those families through the process.
A school that knows its graduates well will answer specifically. A school that does not will talk in general terms.
Kent School eighth graders have gone on to boarding schools including Lawrenceville, Mercersburg Academy, Woodberry Forest, The Hill School, St. Andrew's, Avon Old Farms, and Wyoming Seminary; to independent day schools including The Gunston School, Key School, Severn School, Sanford School, St. James School, Sts. Peter and Paul, Caravel Academy, and Spalding; and to Queen Anne's County High School and the STEM Academy at Kent County High School. We support families through the whole process, from exploration to application, and publish a Secondary School Guide to help families navigate it.
Understand what the tuition actually covers
Published tuition is not a like-for-like comparison between schools. Some quote a number and then bill books, technology, athletics, and field trips separately across the year. Others include most of it.
Ask for the total a family in that grade typically pays across a full year, not the headline figure.
Ask too about tuition assistance, which is more widely available than most families expect. Across independent day schools nationally, around a quarter of students receive some form of aid.
Kent School's tuition is inclusive of academic fees, books, supplies, and most school-sponsored field trips. Middle School tuition for 2026-27 is $21,500. More than 39% of our families receive tuition assistance, with an average award of about $8,681 this year. See our full tuition and affordability information.
Look for something the school does that nobody else does
Most schools will tell you they offer strong academics, small classes, and a caring community. Nearly all of them mean it. What separates one school from another is usually something specific and local that could not be copied somewhere else.
Ask what the school does that no other school nearby does, and listen for whether the answer is a program or a slogan.
At Kent School, the answer is the Chesapeake Bay. Our Bay Studies program runs from PreK through Grade 8 on our own waterfront campus, and it is woven through the curriculum rather than being a field trip. Middle schoolers monitor water quality on the Chester River, study wetlands and shorelines firsthand, and work on the human impact on the watershed across science, literature, and art. The school is a Maryland Certified Green School, recognized by the Maryland Association for Environmental and Outdoor Education, and we partner with the Chesapeake Bay Foundation, the Sultana Education Foundation, and Echo Hill Outdoor School.
Ask who is watching your child, not just teaching them
Middle school is when friendships shift, confidence wobbles, and children become much less likely to tell a parent what happened at school. Ask who in the building would notice, and how that is structured rather than left to chance.
Kent School middle schoolers belong to an advisory group, which is a small group with one teacher who knows them well and stays with them. They also have leadership roles in student government and service learning, and chances to speak, perform, and work alongside students in other grades.
Middle school in Maryland: the practical picture
Kent School serves families across the Eastern Shore and beyond, including Chestertown, Kent County, Queen Anne's County, Centreville, Church Hill, Rock Hall, Easton, and families crossing the bridge from Annapolis and Anne Arundel County.
We are an independent, co-educational day school for PreK through Grade 8 on a waterfront campus in Chestertown. Grades 5 through 8 make up our Middle School.
Common questions
How much does private middle school cost in Maryland? It varies widely, because the statewide average includes parish schools and independent schools together. Ask each school what its tuition includes, since that changes the real figure more than the headline number does. Kent School's Middle School tuition for 2026-27 is $21,500, inclusive of academic fees, books, supplies, and most field trips.
What class size should I expect at a private middle school? Most independent schools run between twelve and eighteen students in a class. Kent School averages about 15.
Is financial aid available for middle school? Yes, at most independent schools, and more widely than families expect. More than 39% of Kent School families receive tuition assistance.
What grades does Kent School's Middle School cover? Grades 5 through 8, within a PreK through Grade 8 school on one campus.
When should we start looking? Most families begin the year before they want their child to start, often in the fall. Kent School admits on a rolling basis, so there is no single deadline and applications are reviewed as they arrive. Starting early gives you the most choice of places, but it is always worth asking, even mid-year.
What happens after eighth grade? Kent School graduates go on to boarding schools, independent day schools, and public high schools across the region and beyond. Our Secondary School Process page lists recent acceptances and explains how we support families through the application process.
Come and see for yourself
No page can tell you whether a school is right for your child. A morning on campus will.
We would rather show you the campus, the classrooms, and the students than describe them.
