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.

Ashley Dierkes

Birch Room Teacher

Born and raised in Southern Vermont, Ashley knew she wanted to work with children from a young age. She joined the Hilltop community in 2021 as an Assistant for the Children’s House and AfterCare Program. She is currently earning her Early Childhood Education degree through the Community College of Vermont. Ashley has had experience working in other childcare centers and has found a great fit with her values in the Montessori philosophy found here at Hilltop, and aspires to obtain her Montessori certification and become a lead teacher! Outside of the classroom, Ashley enjoys spending her free time outside with her cat, Astro, and guinea pig, Duke, and connecting with family and friends with activities like hiking, kayaking, or snowboarding. Creating art has been an important form of expression for Ashley since she was a child. These days pottery and drawing are her favorites.

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 Primary classroom for 2 years but found an almost gravitational pull towards toddlers and the extraordinary levels of independence she saw from these very young children in Montessori environments. She was then inspired her to attend the Montessori Institute in Denver where she obtained her AMI (0-3) Assistants to Infancy diploma. She gained pivotal insight into the 0-3 journey 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.

With her passion and dedication to Montessori as a pedagogy and tool for self-liberation, Lily will be graduating 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 educational research and is excited to be conducting her own research as she completes her Masters. Lily uses her keen observational skills each day to inform her teaching practices and interactions with children in her care. 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, hiking with her husband Ben, a native Vermonter, traveling to new places, and playing ukulele. Lily is thrilled to be joining the Hilltop community this Fall and hopes to bring her passions for music, exploring the outdoors, and food preparation to the Toddler Program.

Laura Gypson

Toddler Program Assistant Teacher & 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

Toddler Program Teacher

Haley is very excited to join the Hilltop community! She grew up in Jamaica, VT and has always wanted to live and work locally.  Haley has an Associate’s in Liberal Arts from GCC. She has always been interested in working with children, and is ready to immerse herself in the Montessori learning style!
In her free time, you can find Haley hiking, reading a good book, writing, and spending time with friends and family, especially her three nephews.

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.