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Our School

Sleepy Hollow Middle School

Sleepy Hollow Middle School consists of 6th through 8th graders and a dedicated faculty. We’re steeped in history and made up of many different nationalities, languages, and cultures. We utilize a TEAM model, with two teams per grade and a core group of teachers. All students from Sleepy Hollow Middle School enter Sleepy Hollow High School with at least two high school credits.

Every September we host “Noone Eats Alone Day,” where we combine all three grades and have a giant picnic to welcome students to the new academic year. Our crown jewel of events is a three-day trip to Washington D.C. taken by our 8th grade students.

Our Principal

Thomas Holland

Thomas Holland

Principal, Sleepy Hollow Middle School

Welcome to Sleepy Hollow Middle School! On behalf of the entire school community, we are honored to be able to work with your child! It is our goal to work with you in order to help your child become a curious, life long learner with the skills necessary to be a critical thinker and problem solver in our ever-changing world.  

Our classrooms are designed to create a safe and caring learning environment that supports all students. In celebrating our diversity we recognize that all members of our community have much to contribute and gain by learning from each other. Embedded within our instruction are opportunities to foster the development of a shared set of principles and values to help us flourish as a community of respectful, responsible and empathetic human beings.

At Sleepy Hollow Middle School, we value the importance of feedback and a strong partnership between home and school. We encourage you to reach out to staff when you have a concern or a question.

To learn more about our programs, please feel free to navigate our website where we will be sure to update you on all our special events and activities this year.  Together we want to wish you and your family an exciting and fulfilling academic school year.

Mr. Thomas Holland & Staff

“One of the greatest and simplest tools for learning more and growing is doing more.”
- Washington Irving

Assistant Principal

Mayerlin Strippoli

Mayerlin Strippoli

Assistant Principal, Sleepy Hollow Middle School

As an educator, I am privileged to serve as Assistant Principal, with a long-standing commitment to the district since 2004. One of the aspects that truly sets the Public Schools of the Tarrytowns apart is its remarkable diversity, which I wholeheartedly embrace and value.

As someone who has personally experienced the journey of learning a second language, I approach education with utmost reverence. Drawing upon my own experiences and embracing my rich cultural background, I strive to establish meaningful connections with my students. I value these connections that don’t end in June but have continued well into college and after for so many of my previous students.

My journey within the district initially began with my dedicated efforts to establish the Dual Language program, a testament to the value I place on bilingualism and inclusivity. Over time, my passion has evolved to encompass teaching science and instilling a profound appreciation for our environment, fostering a genuine love for learning amongst my students.

Front of Sleepy Hollow Middle School building

Contact Us

Sleepy Hollow Middle School
210 North Broadway,
Sleepy Hollow, New York, 10591

Main Phone: 914-332-6275
Fax: 914-332-6546

Nurse's Office: 914-332-6217

DASA Coordinator: Tom Holland & Mayerlin Strippoli 914-332-6275