Ailey’s first day of Kindergarten is quickly approaching and she has a lot of questions about the new school year. We are trying our best to prepare her for what will be a huge shift in her school experience! Here are my First Day of Kindergarten Tips for children and parents.

A Parents’ Thoughts on Starting Kindergarten
For the last three years, Ailey attended an amazing private preschool/pre-K school. Her days were spent in a warm nurturing environment with lots of hugs to go around – her classroom felt like home and the people there felt like family. She is entering a whole new world in elementary school that may feel a little uncomfortable at first.
When I think back on Annabelle’s transition to Kindergarten, I recall her first day (and first few weeks) to be both thrilling and exciting. However, a month into her school year we encountered an unfortunate bullying situation. This had a huge impact on Annabelle and we worked very hard through the following weeks to ensure she felt safe and comfortable going to school every day.
Then, just when things felt right during the winter of 2020, the world shut down due to the pandemic. Annabelle finished her first year of Kindergarten virtually! We hope Ailey has a much better experience in Kindergarten than her big sister.
First Day of Kindergarten Tips
- Discuss what school will be like BEFORE the first day! Read a book, watch a t.v. show (we love Daniel Tiger!), and talk A LOT about school.
- Attend orientation or a meet-and-greet. Take advantage of any opportunity your school may offer to tour the building or meet the teachers. It’s hard for a child to imagine a place if they have never been!
- Ask the Back to School Fairy to make a visit. Magic makes everything better, right? The Back to School Fairy can visit anytime the week before school starts. Our fairy brings a story for the night before the first day, as well as a new lunchbox. Even if you have an older child, surprise him or her with extra school supplies, like Post-It notes (my favorite).
- Make Jitter Glitter the night before school starts! (Read about Jitter Glitter here).
- Read The Night Before Kindergarten.
- Eat a healthy (but not too filling) breakfast!
- Include a surprise picture or note in your child’s lunchbox!
This is our favorite book to read the night before Kindergarten!
First Day of Kindergarten Checklist for Kids (by a kid)
- A healthy lunch
- School supplies (a folder, pencils, just ask your teacher)
- A backpack
- Your favorite snack
- A water bottle
- Change of clothes (pack an outfit + socks in a Ziploc bag for emergencies)
Tips for a Kindergartener from a Third Grader
“Don’t be scared if none of your friends are going to the same school as you because you will make new friends instead.”
“Starting a new school year is fun because you get a new teacher, a new classroom, and to learn new things.”
“You will get to do specials like gym, music, computer, art and library. My favorite special is gym because I like to learn new activities and get exercise during the day.”
Kindergarten Prep Checklist for Parents
- Prep your child for the new school year schedule a few days before school actually starts. Check out this post: How to Have a Stress Free School Morning with Kids
- Gather school supplies – here are 8 ways to save money back to school shopping!
- Label EVERYTHING – supplies, backpack, water bottle, etc. – so you don’t have to worry about losing your child’s new school items. Use code caitlinhoustonblog10 for 10% off Label Land!
- Talk with your child about their favorite lunch items and visit the grocery store together. Check out these 25 Easy School Lunch Ideas.
- Go through clothes and donate items that are too small – then plan a fun back to school shopping trip! Who doesn’t love picking out a new outfit for the first day of school?
- If you’re feeling stressed/anxious/sad, remember to breathe 🙂
Check out my list of Back to School Tips for Parents here
Looking back, I recall crying both on the way to and home from dropping Annabelle off on her first few days of school (not just the first). I struggled most with knowing how much she would change – as a former first grade teacher I watched it happen year after year with my students. Peers have A LOT of influence over your children!
Since Annabelle went to Kindergarten I have learned a lot about adjusting to the new chapter of life. I know the importance of talking about the positives from school each day – don’t let your child focus on negatives! I also remember allowing ample rest time after school – your child will be exhausted! Kindergarten is just the beginning of a whole new experience for our kids; it’s both scary and exciting!
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