Isabel Greenbaum Stone, Founder of The Windward School, New York

Isabel Greenbaum StoneFounder

In 1926, two teachers–Agnes Inglis and Eleanor Foster– and a parent, Isabel Greenbaum Stone, formed a progressive day school with 21 students in an old real estate office in New Rochelle. They called it, "Windward,"  because sailing windward requires more skill, effort, and persistence than sailing before the wind. Careful records were kept and the cooperation between teachers and parents defined the school's philosophy. They believed that every child had their own unique potential and groups were determined by the needs of the child. The school environment was adapted to students' needs and it was more about cooperation than competition.


In 1927, enrollment doubled and the School was moved to a house in New Rochelle on Quaker Ridge Road. Windward officially became a member corporation made up of members consisting of faculty and parents. 


Plans were made to build a new building as enrollment continued to grow. In the 30 May 1930 issue of the Scarsdale Inquirer, pupils who lived in Scarsdale and attended the Windward School in New Rochelle were identified as presenting a group of six plays and that earlier in Spring 1930, a bazaar had been given by the children, with articles for sale that had been made in shop class, to sell with proceeds benefiting the new school building in White Plains which would be ready for occupancy in October.

“...the school got its name because the imagery of sailing into the wind was so fitting to all the difficulties involved in establishing it,” says former  Assistant Head and Director of Admissions Maureen Sweeney. “Our founder, Isabel Greenbaum Stone, had three boys and she was looking for a good independent progressive school for them to get into. After many travails, she managed to find two teachers she liked. Then she decided to buy seven acres of land right in White Plains. And the Windward School was formed.” - "Windward School: Special Education At Its Best" - Education Update, June 2002

Windward School in Scarsdale Inquirer news article 1930

An article clip from the 30 May 1930 issue of The Scarsdale Inquirer

In November 1930, and with an enrollment of 99 students now, the Windward School moved to a brand-new building styled in after an English manor house on 13 Windward Avenue in White Plains, New York.

Classes continued to remain small and flexible despite growing enrollment, and each child was educated as an individual. The program sought to foster a love of learning and feeling of success.

As time went on, additions were made to the building and housed 200 students in preschool through eighth grade.

Students run in the back of the English-style Manor building at 13 Windward Ave. in White Plains, NY.


Windward School holds a benefit featuring Robert Crawford, later known as the "Flying Baritone" and known for writing "The U.S. Air Force Song," with proceeds devoted to the scholarship fund. Windward School is described in the Scarsdale Inquirer as a progressive day school for "boys and girls from nursery through junior high school...the modern school building stands on a five-acre plot. The enrollment of 100 pupils includes children from White Plains, Larchmont, New Rochelle, Scarsdale, Pelham, Greenwich, Ossining, and Pleasantville."


Mr. Leslie Brown of White Plains is elected director of the Windward School by the board of trustees. Additionally, Miss Marjorie Dunn of Scarsdale, was named assistant director.


Miss Marjorie Dunn is appointed director of the Windward School. 


The Windward School has been opened for 19 years and educates 91 children, the largest number of enrolled students in years.


Mr. Ronald Pavlak named director of the Windward School.


Dr. Elmer Kane appointed director of the Windward School. At this time, the School offers programs from nursery school through ninth grade.


In 1976, the Windward School was registered with New York State as a school for learning disabled students in grades K-8. The mission was not yet clarified and included a broad range of students. At this time, the school serves 89 students.


The school starts to serve high school students


Dr. Judith C. Hochman becomes head of school. The student profile is more defined to be students with language-based learning disabilities of average to superior potential and available to learn. Curriculum becomes research-based and students are directly instructed in a group model. The focus of the school is remediation not accommodation for students with the goal being to return students to mainstream settings once remediated. At this time, the School serves 129 students.


The campus at 13 Windward Ave. expands beyond its original building, doubling its size by adding 14 additional classrooms, a full-size gymnasium, science and computer labs, a teachers' lounge and staff offices. At this time, the school serves 259 students.

Rendering of expansion of 13 Windward Ave in 1994

In 1994, Windward Teacher Training Institute (now known as The Windward Institute) is established to provide professional development based on scientifically validated research in child development, learning theory, and pedagogy.


Dr. James Van Amburg becomes head of school.


The campus at 40 West Red Oak Lane in West Harrison, NY, (now known as The Windward School Westchester Middle School) opens for grades 6-12. Additionally, it is the first dedicated space for the Windward Teacher Training Institute (now known as The Windward Institute). The Windward School serves just over 400 students.


In Spring 2004, The Windward School officially graduated its last high school senior class, so the School could focus more on early intervention of children with language-based learning disabilities. With two campuses, grades 1-4 are now at the 13 Windward Ave. campus, and grades 5-9 are located at the West Red Oak Lane Campus. 


Dr. John J. Russell becomes head of school.


Windward Teacher Training Institute (now known as The Windward Institute) receives accreditation from IMSLEC (The International Multisensory Structured Language Education Council). This accreditation enables the WI to offer national certification in Multisensory Structured Language Education to teachers at Windward and other schools. The professional development program offers extensive coursework and supervision leading to a professional certification. The International Dyslexia Association recognizes all IMSLEC-accredited training programs for meeting IDA's Knowledge and Practice Standards for Teachers of Reading.


The West Red Oak campus expands to include an auditorium to hold drama performances and presentations, more space dedicated to professionally develop Windward and outside teachers, including classrooms for courses and workshops; an art gallery; and an office suite for additional administrative offices.

A new Manhattan campus is announced to be located at 92nd Street b/w Second and Third Avenues.



Manhattan Lower and Middle Schools temporarily opens on Upper West Side.



While The Windward School Manhattan Lower and Middle Schools officially opened in Manhattan in 2015, it moved to its permanent space at 212 E 93rd Street in Fall 2016 with 205 students in grades 2-7 on the first day of school. The Windward School, with three campuses serving children with language-based learning disabilities, now serves 795 students.

Collage of photos for Manhattan Lower and Middle Schools opening in Fall 2016


Manhattan Middle School adds an eighth grade. With three campuses, The Windward School transforms the lives of 862 students.



The Windward Summer Program, a four-week academic enrichment program in July for students in all academic settings, expands to Manhattan.


Jamie Williamson becomes head of school.

Jamie Williamson stands with Westchester Lower School Students on first day of school 2019

In August 2019, The Windward School closes on the future Westchester Lower School campus located at 1275 Mamaroneck Avenue in White Plains, New York. Purchasing this campus will allow 150 additional seats to be available over time for students who need a Windward education.


Windward Teacher Training Institute formally becomes The Windward Institute and the Windward Teacher Training Program in January 2020.

Due to the COVID-19 pandemic and in order to accommodate all students for in-person instruction for the 2020-2021 school year, the 1275 Mamaroneck Avenue campus opens for Westchester Lower School grades 1-4 and Westchester Middle School grade 5 on October 28. Additionally, Manhattan Lower School moves to a temporary space on the UES that the School utilized in 2015.

With four campuses, The Windward School enrolls 941 students for the 2020-2021 school year.



For the 2021-2022 school year, grade 5 became a part of the lower schools.

We are seeking history of The Windward School throughout the 20th century, especially from 1930-1976. Please email communications@thewindwardschool.org with any info you may have.

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