Westchester Middle School


Grades 5-9 for the 2019-2020 school year

The Westchester Middle School houses 380 students in grades 5–9 and 90 faculty members. Students build warm and trusting relationships with their teachers in a structured environment where expectations are clear, and care for each student is paramount. In addition to the neatly organized classrooms, students enjoy a large gymnasium, an auditorium, a cafeteria, two art rooms, five science laboratories, a library, a computer lab, and playing fields for recess, intramurals, and competitive sports. We enjoy hosting visitors and showing them our building and our program.

To schedule a tour, please fill out the admissions inquiry form.


Westchester Middle School Program

Windward's Westchester Middle School (grades 5-9) provides a strong instructional program where students acquire academic proficiency, learn self-advocacy skills, and build self confidence in an environment that nurtures each child’s personal and social development.

Since all Windward students have difficulties in the areas of reading and writing, the language arts program is the core of the School’s curriculum. Through direct instruction in small, homogenously grouped settings, children are explicitly taught the rules of language necessary for comprehending, remembering and communicating information. Students receive 3 periods of language arts daily which includes reading, expository writing, vocabulary development, study skills and phonics-based reading instruction based on The PAF Reading Program by Phyllis Bertin and Eileen Perlman. Lessons for writing linguistically complex sentences and paragraphs, outlining, note-taking, paraphrasing, and summarizing are integrated across the curriculum. Students then use these writing techniques to develop research papers in conjunction with assignments in other subject areas, and they become proficient in using the library and the Internet for research. In addition, all students have one period of math, science, and social studies daily.

Math lessons at Windward are created to teach computational and application skills, enhance conceptual understanding, and develop each child’s ability to communicate using the language of math. Homogenously grouped classes enable teachers to build a solid foundation of basic math concepts, computation and number sense. Classes range from remedial to advanced and instructional techniques are adapted to support individual learning differences.

The science and social studies programs at the middle schools are guided by New York State curriculum standards and strive to integrate content, concepts, and skill learning while reinforcing the student’s reading and writing competency.

Our physical education program helps promote the student’s mental, physical and emotional well-being while the Arts provide an arena for children to develop poise and confidence and the opportunity for creativity and self-expression.

Windward's middle schools have a developmentally appropriate group guidance curriculum. Fifth, sixth, and seventh graders receive bi-weekly lessons taught by guidance counselors in a group setting. Eighth-grade students take part in a weekly GAINS program (Getting Ahead In School). The purpose of GAINS is to provide students with accurate information about learning differences, help them to gain insight into their strengths and weaknesses, become better self-advocates, and be better prepared for their transition to high school. In the ninth grade, students participate in a weekly advisory period where they discuss relevant teenage issues, practice public speaking skills and participate in community service projects.

The Windward School provides an educational experience that emphasizes skills and develops the independence, initiative, and academic and social confidence that each student needs to successfully return to the mainstream setting.

Arts Program

Building on the lower-school curriculum, the Westchester Middle School's art department continues to hone the Windward student’s familiarity with art tools and media at increasingly complex levels. Additionally, new media are introduced such as ceramics, printmaking, metal work, woodworking, color theory, and portraiture. Principles of art and design such as unity, balance, contrast, and proportion are defined and applied as are the additional art elements of value, texture, and form. Through visual, aesthetic, and auditory models, students continue to develop their language skills.

While middle-school art teachers continue to use direct and explicit multisensory teaching methods, students are given more responsibility in the art room. They are asked to think and do for themselves at developmentally appropriate levels. This greater emphasis on student autonomy yields more diversity in artwork and produces more independent artists who are preparing for eventual entry into mainstream school environments. Students continue to experience interdisciplinary projects at Westchester Middle School, and they have the opportunity to showcase their accomplishments at our annual Westchester Middle School Art Exhibition as well as in the gallery and halls throughout the school year.

Drama & Chorus Program

The mission of the Windward Drama Program is to offer challenging creative opportunities in a supportive environment. Taught in the Middle School as part of the 6th grade curriculum, it is also offered as an elective club to Middle School students at all grade levels.

The program provides an outlet for self-expression, instills confidence, increases self-esteem and engages the imagination. Involvement in drama club productions teaches responsitibility and commitment while also fostering a sense of community and developing new friendships. The Windward Drama Program encourages students to take risks and discover new talents.

The Windward drama class is a multi-sensory, language-based experience. Through acting exercises and scene work, students improve their ability to read with expression, expand their vocabulary, improve their public speaking, and sharpen their memorization skills. Through collaborative playwriting, students utilize skills taught in the Windward reading and writing programs. They learn the vocabulary of dramatic literature and develop skills for creative problem solving. The elective Windward Drama Club meets for rehearsals after-school and during lunch. The Drama Club produces two shows annually; recent shows have included, “A Midsummer Night’s Dream,” “Oliver,” and “Guys and Dolls.” Students may participate as performers or tech and backstage crew.

Students may also elect to participate in the Westchester Middle School Chorus. In chorus, students learn to sing musical selections in three-part harmony while building teamwork skills and cooperation. Participation in chorus helps refine listening skills and improve focus. There are one or two chorus concerts annually. Musical selections consist of Broadway show tunes and popular music from different eras. Music is chosen to introduce students to varying tempo, style, and articulation.

Physical Education

The program for students in the fifth and sixth grades builds upon the lower school curriculum and is based on skill acquisition, creative drills combined with lead-up games and game play. Seventh and eighth grade students review the fundamentals of sport specific skills and engage in team scrimmages. They also have the opportunity to enroll in elective activities, which include Zumba, yoga, fitness, rollerblading, and dance. The ninth-grade curriculum is unique in that it is aimed at fostering an interest in lifetime sports such as tennis, bowling, golf, and skating. The middle school's physical education curriculum places a strong emphasis on fitness, teamwork, sportsmanship and activities that foster an appreciation for a healthy lifestyle. In all classes, students are introduced to age appropriate skills, concepts, rules, and strategies, and are given opportunities to practice those skills via drills, cooperative activities, creative games, and scrimmages.


The Westchester Middle School Athletics Program is designed to enhance students’ personal development and athletic abilities through the teaching of sound skills, sportsmanship, and teamwork. The School boasts a variety of interscholastic and intramural teams and clubs, allowing students to excel in an area of their choice while representing the Windward community. Students of varying athletic abilities participate together on teams whose primary goals are to model and promote self-esteem, school spirit, fundamental skills, and love of the game. The coaches successfully incorporate many of the same teaching strategies used in the classroom to instruct our students on the field. All students are encouraged to participate in after school athletics through which they can enjoy competing with friends while building character and developing life skills.

Windward athletes compete against neighboring schools in the Fairchester League, a consortium of independent schools in Westchester County, NY and Fairfield County, CT. In keeping with Windward’s philosophy, the league emphasizes fair play, teamwork, and participation over winning. Interscholastic sports offered at Windward include fall and spring cross-country, soccer, basketball, squash, lacrosse, and softball.

Intramural and instructional sports include volleyball, cheerleading, basketball, tennis, and fencing.

Clubs & Activities Program

The Westchester Middle School Activities Program is primarily an after school program designed to bring students in grades five through nine together in less structured, informal settings. Trips are usually conducted on Fridays following dismissal, and our destinations are varied. Trips are occasionally restricted to one particular grade, but most are open to all interested Middle School students. The first trip of the year is usually to an area entertainment center where students can play mini-golf, ride go-carts, and enjoy laser tag games with friends. The School takes advantage of its proximity to New York City by offering students the opportunity to take trips to Broadway shows, professional sporting events, cultural institutions, and museums. Each trip usually includes a dinner at which students can socialize with their peers, and all trips are chaperoned by Windward faculty members. The costs of the trips vary, and stipends are available to subsidize families in need.  

List of 2019-2020 After-School Friday Afternoon Trips

Trips that take place during the school day have an educational component and generally reflect the students’ social studies or science curricula. In past years, Fifth grade students have visited  a Revolutionary War re-enactment in Westchester County to supplement their study of this period and Museum Village in Monroe, New York while sixth grade students traveled to the Metropolitan Museum of Art to view the Museum’s vast Egyptian collection. The Museum of the Moving Image is usually the destination for a seventh grade trip, while eighth graders might visit the Tenement Museum, 9/11 Museum, or Museum of Natural History in New York City. The ninth grade often takes an overnight trip that relates to a particular theme the grade studies during the year. The School also reserves time for each grade to take a year-end trip in June; these trips aim to be both educational and fun. Past destinations have included the Intrepid Sea, Air and Space Museum; Medieval Times; and a tour of an anthracite coal mine museum in Pennsylvania, among others.

Windward also offers a variety of clubs. The offerings are usually generated by student interest and meet either during recess or after school. Recess clubs meet one to five times each week while after-school clubs typically meet from 3 P.M. to 4:30 PM one day per week. Past clubs have included a meteorology club, art club, ping-pong club, chess club, duct tape club, history club, and cooking club. These clubs may meet for the entire year or for a three month period. Other clubs are established by the Guidance Department from time to time in order to address issues pertinent to particular groups of Windward students. Most recently, a 5th grade “Girls Club” was held one day each week at lunch.

Students are encouraged to speak with Mr. Steiker, Director of Activities, if they wish to start a new club.

Contact Us
phone: (914) 949-6968
Fax: (914) 696-0904

Christopher Q. Eberhard
Division Head, Westchester Middle School
Ext. 1262

Amy Hughes
Assistant Division Head
Westchester Middle School
Ext. 1277