This year, the Canterbury community honored Ms. Alison Bailey as the 2019 recipient of the Woman of the Year Award. The Woman of the Year Award serves to honor and recognize someone in our community who not only inspires those around her but someone who actively works to improve and positively impact school life. Overall, the Woman of the Year truly exemplifies the qualities of the values of the school and thoroughly demonstrates what it means to be a strong woman.
Alison Bailey joined the Canterbury community in 2013 and is currently Director of the Donovan Center for Learning and an English teacher. She attended Taft School as a boarding student for four years and graduated St. Lawrence University with a bachelor’s degree in English literature. Before joining the Canterbury faculty, Ms. Bailey worked as an English teacher, college counselor, and tri-varsity coach at Northwood School in Lake Placid, NY. She also taught at Fay School, MA and The Pennington School, NJ. Ms. Bailey grew up in New Milford, CT and learned to skate at Canterbury’s O’Neill Arena. In addition to being a teacher, coach, advisor, and colleague, her greatest role is that of a mother. Ms. Bailey lives on campus and describes raising her son, Griffin, on the hilltop as an extraordinary experience.
On a daily basis, Ms. Bailey demonstrates care, compassion, and an unwavering commitment to every Canterbury student. Her work in the Donovan Center takes the form of a true partnership with students, inspiring their confidence in myriad ways and nurturing their achievement toward both academic and personal goals. Ms. Bailey was chosen as Canterbury School’s 2019 Woman of the Year because her passion, grace, and smile are felt widely throughout the entire campus community, and her lasting impact on the success of our students is immeasurable.