A Pre-Kindergarten - Grade 12 co-educational independent day school in Westchester County, New York

Rye Country Day School Names Pen Vineyard Next Middle School Principal

Rye Country Day School is excited to announce Pen Vineyard as the next Middle School Principal. Mr. Vineyard, who is currently Head of Middle School at The Boys' Latin School of Maryland, will begin his tenure at RCDS in July. 

At Boys’ Latin, a K-12 independent boys’ school in Baltimore, Mr. Vineyard is responsible for all aspects of daily operations for grades 6-8, including curriculum, teaching and learning, counseling and support services, division strategy, and parent/guardian collaboration.

Known for his top priority to instill in his students a sense of belonging, Mr. Vineyard joined Boys’ Latin in the height of the pandemic as Associate Head of Middle School and leaned into building trusting and constructive relationships. In his words, “Relationships create belonging, and from that sense of belonging, incredible things can start to happen.” As a result, his leadership was fruitful and effective. He became Head of Middle School in 2021.

The many accomplishments during Mr. Vineyard’s tenure at Boys’ Latin include devising plans to return to in-person learning in the pandemic fall of 2020, helping to build and launch a new boarding program, recruiting outstanding faculty, contributing to DEI efforts, and expanding elective offerings. A passionate teacher, Mr. Vineyard has also kept his connection to the classroom, teaching Spanish (grades 6-8) and Latin (grade 8) during his years at Boys’ Latin. Before becoming Middle School Head, he also served  as a cross country coach and an eighth-grade advisor.

Prior to Boys’ Latin, Mr. Vineyard served on the senior leadership team as Dean of Students at Fairfield Country Day School, a K-9 boys’ school in our Fairchester independent school consortium. In that role, he supported diverse learning and social-emotional needs for students in grades 5-9, managed student discipline, refined advisory, student diversity club, class trips, and other programs, oversaw teacher comment reviews, and developed FCDS’s first-ever mini-mester courses. He also served on important school committees, including head of school search, retirement pension planning, website redesign, faculty evaluation, DEI, and accreditation. In addition, he taught Spanish (grades 5-9), Latin (grade 6), and algebra and geometry (grade 8). 

While at FCDS, Mr. Vineyard had the pleasure of connecting with RCDS faculty and students as a regular participant in the Middle School Mosaic Conference. In 2019, he was selected to lead the FCDS Boys Lab, an innovation center to further strategic partnerships and programmatic innovation, and his colleagues named him a recipient of the Finerty Award, the highest faculty honor at FCDS.

Mr. Vineyard is a seasoned Middle School expert who has shaped curriculum and organized professional development around relational learning, executive functioning, student leadership, and social-emotional learning. He has also partnered with families to develop parent education programming and strengthen the crucial home-school collaboration of the middle school years. Having worked in both K-9 and K-12 schools, Mr. Vineyard understands the importance of student transitions from lower to middle school, from middle to upper school, and from upper school to college. He is proud to be a middle school educator and leader because he understands the impact and potential of the middle years as the fulcrum of a student’s pre-college academic journey.

Mr. Vineyard is a graduate of Dartmouth College—he received his B.A. in music and graduated in three years with cum laude honors. He earned his M.A. in Private School Leadership from the Klingenstein Center at Teachers College, Columbia University. He also holds certification to teach Spanish in Connecticut Public Schools. Mr. Vineyard is multilingual, fluent in English and Spanish and proficient in French. He looks forward to joining this RCDS community with his wife, Anna, their one-year-old, Maya, and their Italian Greyhound, Pintxo.

We look forward to having Mr. Vineyard join the RCDS community in July!

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