Your Child’s First Day at Montessori: A Guide for Letting Go Gently
The first day of school isn’t just a milestone for your child, it’s one for you, too. Here’s how to prepare your little one (and your own heart) for a confident, calm beginning.
The first day of Montessori shapes both the child walking in and the parent letting go. You tighten the straps on their tiny backpack. You walk them to the door. You lean in for one last hug, knowing they’ll be fine, but feeling every second of the goodbye.
This moment belongs to both of you. They begin their journey toward independence. You begin the quiet work of trusting it. So, how do you prepare for your child’s first day at Montessori? How do you help them walk in with confidence and steady yourself as they do?
First Day Feelings Are Normal (Yes, Yours Too)
At The Mint School, we’ve welcomed hundreds of children on their first day. We’ve seen it all: the eager wave-and-go, the tearful clinging, the slow transition with tiny steps and big feelings. What matters most isn’t how they separate, it’s that they feel safe, seen, and supported throughout the process. And yes, that goes for parents, too.
“Transitions are emotional,”
says Saarah Shivji, J.D., Executive Director at The Mint School.
“We encourage parents to acknowledge those emotions, not suppress them. Children are intuitive, when they sense you trust the space, they begin to trust it too.”
First Day Preparation Starts at Home
Montessori encourages independence, even in toddlers. And that’s not something that magically appears on Day One, it begins at home. In the weeks leading up to your child’s first day, build small routines that mirror the classroom experience:
- Let them carry their backpack.
- Encourage them to choose their outfit (Mint’s optional uniform makes this easy).
- Label belongings together (backpack, water bottle, indoor shoes) and show them where everything goes.
- Practice saying goodbye and hello.
These small routines prepare your child for what’s ahead. They show that change can feel safe, routines bring comfort, and independence comes with support.
Visit the Classroom Before the First Day
Familiarity builds confidence. At Mint, we encourage you to tour during classroom hours when possible. Let your child explore the space, meet the teachers, and handle the materials. These early moments help them form a mental map they’ll return to on their first day.
“The hum of purposeful work, the calm of the environment, it all speaks to the child long before we do,” says Shivji.
If you haven’t toured yet, schedule a visit and explore the classroom together.
Keep Goodbyes Short and Certain
Here’s the golden rule of Montessori drop-offs: never sneak away. It may seem kinder in the moment, but it undermines your child’s sense of security.
Instead, develop a “goodbye ritual.” A high-five, a hug, a whispered phrase (“Have a lovely day, I’ll see you in the afternoon!”), then, walk away. Even if it’s hard.
When they step inside, they enter a calm, focused, and meticulously organized classroom, an environment where children feel accepted and ready to explore from the moment they arrive.
Trust the Process (and the Professionals)
Your child’s first day isn’t a performance. It’s not about how fast they join an activity but how safe they feel doing it. At Mint, we follow the child’s pace.
If they need a shorter day for the first week, we’ll plan that with you. When children feel respected from the start, they feel empowered every day after.
Support Yourself, Too
You can’t pour from an empty cup, especially not when your heart has just walked into a toddler classroom with a dragonfly backpack.
Give yourself grace. Text a friend. Take a walk. Or sit in the quiet and feel what you feel. This is a big step for you, too. Many parents find their own confidence grows as quickly as their child’s. The proof arrives quietly: when your child says they poured their own water, zipped their coat, made a friend.
These small wins begin on the first day and keep growing from there.
To learn more about our Enriched Whole Child Curriculum and bilingual Montessori programs for toddlers and Casa learners, visit The Mint School or book a tour.