To our future pupils and parents; Croeso and Welcome to our Transition 2022 page. You will find everything you need to inform your/your child's transition to Chepstow School in September 2023. More content is being added by the day, so please check back often for updates!

You can also check our dedicated Transition Twitter Page for regular updates: @PrimaryTransit1

Welcome to Chepstow School

Chepstow School - Drone Tour

Chepstow School - Minecraft Tour

Joining Chepstow School


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Academic Tasters

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Academic Taster - ENGLISH
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Academic Taster - SPANISH
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Academic Taster - SCIENCE
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Academic Taster - HUMANITIES
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Academic Taster - ART
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Transition Staff


Ms S. Miller
Head of Year 7

Hello, my name is Ms Miller and I am the Head of Year 7 at Chepstow School. I am a music and drama teacher from Year 7 up to Year 13. I’ve been teaching for 7 years so far, the last four have been here at Chepstow.

I am really excited to get to meet you all and see what kind of characters and young people will make up our new Year 7. I am excited to learn about what kind of Year 7 we will be – what would you like our focus to be? Will we raise money for charities? Will we decide to focus on good deeds in our community? Perhaps we will work on improving the environment of our school site. I would love to hear your ideas in anticipation for next year – please feel free to email or tweet me with your ideas.

I live just outside of Chepstow with my partner, two little boys and our cat. I love gardening, singing, walking and dancing!

Miss C. Roullier
Learning Coach (ELSA)

Hello, my name is Clare Roullier and I am the ELSA at Chepstow School. 

I know the first thing you will think is, "what is an ELSA?" and your second thought will be the film Frozen, but I can assure you I will not be singing “let it go” at you (only if you request it).  Let me explain: an ELSA is an Emotional Literacy Support Assistant. It is my job to ensure that you are happy at school to help you reach your full potential academically.  My aim is to help remove any barriers to learning and help you all be happy, secure children whilst at school and at home.

I am really looking forward to meeting you and being part of the exciting year ahead with you all in Year 7.  

Miss C. Thomas
Year 7 Form Tutor - 7C

Hey everyone, I’m Miss Thomas. I am a Computer Science teacher at Chepstow School and I’ve been teaching at the school for one year now. I am so excited to meet you all on our first day! 

I am hoping to spend my summer on the sea...paddleboarding, surfing and kayaking. I’d love to hear what you hope to do over the summer, tweet me some of your plans via @CThomasCS. 

See you all in September! 

Mrs H. Casterton
Year 7 Form Tutor - 7H

Hello everyone, I’m Mrs Casterton. I am a 2nd in the Maths department and in charge of KS3 maths; that’s Years 7, 8 and 9. I’ve been teaching at the school for 11 years now. I am so excited to meet you all on our first day! 

I am hoping to spend my summer moving house and enjoying time with my baby daughter who has just started walking! I have a passion for maths and really looking forward to sharing that with you all. 

See you all in September! 

Mr J. Woodland
Year 7 Form Tutor - 7E

Shwmae pawb! Fy enw i ydy Mr Woodland and I am the Head of the Welsh department here at Chepstow School. I am also a Year 7 form tutor - a role that I very much enjoy. I have been at Chepstow School now for one year and I’m sure we will all share the same feelings of excitement in readiness for September! Joining Chepstow School will provide you all with the opportunity to start afresh with a vision of the individuals you want to become tomorrow! I and the rest of my colleagues within the Year 7 team are looking forward to helping you do just that. 

Before joining Chepstow School, I worked as a Teacher of Welsh and also as Deputy Head of Year 7 at Islwyn High School (the school I attended as a pupil). I began my career at Cardinal Newman School, near Pontypridd and I had a Year 7 form class there too! 

As a student, I attended Cardiff University and studied a joint honours degree in Welsh and History. I also love sports; namely Football and Cricket. For the last 8 years, I have been the Head Coach of Blackwood Town Cricket Club’s U13 team. This upcoming academic year will be my 5th in teaching and I’m sure it’s going to be the most enjoyable so far! 


Mrs E. Wilks
Year 7 Form Tutor - 7P

Hello everyone, I’m Mrs Wilks. I am a Humanities teachers and have been teaching at the school for 6 years now. I am so excited to meet you all on our first day! 

I have just moved house so I will be redecorating over the summer and in my free time I’ll be at Llandegfedd Reservoir paddle boarding with my family! 

See you all in September! 

Useful Information and Communications

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Admissions to School - September 2022
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Helping Hands Psychology Transition to School Parent Workshop
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Transition Home Learning Booklet