The Toddler Program

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Jay Cook

Music Teacher

Jay has been the school’s musical pied piper since 1996! He has a BA in Music from Middlebury College and plays an array of instruments. Jay enjoys instrumental and vocal improvisation, and plays bass, keyboard and sings with his bands, Jazzberry Jam and Hipfunk Associates. He introduces rhythm, movement and song to our youngest students; recorder, drums, ukulele, ensemble playing, music technology and collaboration to our elementary students; brings us all together for All School Gathering sings; and does everything possible to have music be integrated into the life of Hilltop Montessori School.

Laura Gypson

Early Education Program Partnership Director

When Laura moved to the Brattleboro area over eight years ago her goal was to teach at Hilltop Montessori School and her path led to our doors in 2020. As an early childhood educator of over twelve years now, she loves the respect that the Montessori model has for the work of every child and the independence which is fostered every day within our school. Laura has a Bachelor’s Degree in Early Childhood Education from Northern Vermont University and holds a Vermont Early Childhood Education Teaching License.

Outside of teaching, Laura lives in Williamsville, Vermont with her partner Gabe. She has a deep passion for music across many genres and spends her time biking, cooking, reading, following baseball and caring for her dog, Percy and cat, Mya.

Haley Hopkins

Birch Room Assistant Teacher

Lily Enchin

Toddler Program Director

Lily (she/her) started her career in Montessori Education in 2017 and earned her MACTE accredited Primary diploma. She worked in a Children’s House classroom for 2 years but found an almost gravitational pull towards toddlers and the extraordinary levels of independence she saw from these young children in Montessori environments. She then attended the Montessori Institute in Denver where she obtained her AMI (0-3) Assistants to Infancy diploma. During training, Lily gained pivotal insight into the life of the child from 0-3 and learned how to not only prepare a Montessori environment for the young child at school, but also in the home. Lily loves working alongside families and supporting new parents as they navigate the first few years of a child’s life. Lily graduated with her M. Ed in Montessori Education from Loyola University Maryland in the Spring of 2023. She is enthusiastic about the growing field of Montessori research and was thrilled to conduct her own research on the topic of parent engagement through parent workshops and community events.

Lily feels joy guiding young children towards functional independence and offering abundant opportunities for them to first care for themselves, so that they can then extend this care to their environment and others. She sees this as the natural progression towards truly feeling a sense of belonging to one’s community.Lily was born and raised in Toronto, Canada and has a Bachelor of Arts in East Asian Studies from York University with a focus on Chinese Language and Culture. Her studies of Asia have taken her to Cambodia, where she volunteered for an NGO offering free English classes to children in rural villages. She also has taught English as a Second Language to children in China. In her free time Lily loves cooking, hula-hooping, hiking with her husband Ben, a native Vermonter, traveling to new places, and playing ukulele. Lily is thrilled to be back at Hilltop for her second year as Toddler Program Director.

Jessica Shelby

Toddler Program Assistant

Jessica grew up in Southern New Hampshire and moved to the area in October of 2022. Jessica developed a passion for working with children during the Covid-19 pandemic as a nanny. During her time as a nanny Jessica learned about the Montessori philosophy and strongly agreed with its principles. After leaving that job to move to Walpole, New Hampshire she eventually found her way to Hilltop. In the future Jessica hopes to earn a degree in early childhood education and eventually become certified in Montessori education.

Outside of school Jessica likes to spend time with family, knit, and cook/bake.

Miranda Sherman

Toddler Program Assistant Teacher

Miranda grew up in Northern Virginia and moved to Colorado in 2008. Just recently, she and her family moved to Vermont to be closer to her East Coast family and feels so grateful to have landed here at Hilltop! She has two littles that will be at Hilltop, too.

Miranda studied Early Childhood Education and started working with toddlers at a Montessori school in 2013. She worked in this environment for four years before getting her yoga teacher certification. She owned and taught yoga to children at Mindful Warriors and additionally taught meditation, restorative, nidra and prenatal yoga to parents. After the birth of her first child, she became a certified Postpartum Doula and worked with mothers, and their babes, integrating mindfulness, breathwork and body awareness until returning to the Montessori classroom in 2022.

She is currently receiving her Infant and Toddler credential at Montessori Education Center of the Rockies. She is very passionate, and excited, about teaching children, parents and guardians about tools to use for nervous-system wellbeing and all things Montessori!