Recently, New York City Department of Education Chancellor Richard Carranza, along with Michael Benedetto, Chair of the NY State Standing Committee on Education and Assemblymember; Jo Anne Simon, Member of the NY State Standing Committee on Education and Assemblymember; Drs. Sally and Bennett Shaywitz, Co-Founders and Co-Directors of the Yale Center for Dyslexia & Creativity; Robert Carroll, Windward alum and New York State Assemblymember, visited The Windward School's Manhattan campus.

Ms. Lori Squillante will be the next assistant division head of The Windward School’s Manhattan Lower School. Ms. Squillante will be leaving her current position as the Westchester Lower School coordinator of math and diversity advisor to assume this position as of July 1, 2019.

On Saturday, April 13 more than 300 members of the Windward community gathered at the Westchester Middle School and Manhattan campuses to volunteer at the first Windward Parents Association CommUNITY Service Day.

In the fall of 2018, a team of educators representing the International Multisensory Structured Language Education Council (IMSLEC), visited Windward Teacher Training Institute (WTTI) for three days to review files, interview administrators and faculty members involved in the IMSLEC process, and examine WTTI's facilities as part of the reaccreditation process for IMSLEC certification. As a result of this visit and many months of preparation by WTTI administrators, faculty, and staff, a perfect score for reaccreditation in multisensory structured language education has been granted to WTTI. No recommendations or limitations were made, and the IMSLEC report stated, "Your program is the gold standard—a model of excellence."