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Caitlin Bailey

Caitlin is enthusiastic to begin her first year as the head teacher at Shelter Island Pre-School. Previously, Caitlin worked at The Child Development Center of the Hamptons where in her two years of employment she worked in many different roles; including being a paraprofessional and teacher’s aide in the pre-school, 1st grade co-teacher, as well as the building substitute teacher. Caitlin enjoyed her time in the pre-school classrooms the most. She received her Bachelor’s degree in Elementary Education from The State University of New York at Plattsburgh and is certified in New York State. In addition, she has a Master’s in Counselor Education. Caitlin believes that children learn best when they are in a fun and comfortable environment that allows them to explore and foster their own learning through unique experiences in the classroom both independently and with the guidance of their teachers and peers. Caitlin is an avid reader and enjoys practicing yoga in her spare time.

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Hannah Gray

Hannah Gray is delighted to be joining Shelter Island Preschool as the assistant teacher for the 2016-17 school year. After receiving a bachelor’s degree from Dowling College, Hannah spent time traveling and working throughout Europe. Upon her return, she moved to the North Fork of Long Island and taught art at Our Lady of Mercy School. Recognizing a need for a more extensive expressive arts environment, Hannah spearheaded a theatre arts program where the children were able to embrace not only their own creative expression but also, a deeper understanding of live storytelling, the stage and the art of bringing a character to life. During her years at Our Lady of Mercy, Hannah attended St. Johns University and obtained a master’s degree in Childhood Education. While studying at St. Johns, she was one of 10 working teachers to receive a Fulbright scholarship in order to teach in Vietnam. After returning from Vietnam, she traveled to Argentina to gain a deeper understanding of children who have and will emigrate from Spanish speaking countries. Hannah strives to live by the Reggio Emilia understanding that “children have a hundred languages”. She is passionate about helping children learn in the spirit of diversity, understanding and kindness. Hannah Gray is owner and director of hapi children’s theatre conservatory. She lives in Southold with her daughter, Ella and sons Bereket and Noah.