From Sandboxes to School Bells: Easing Toddlers Into Back-to-School Mode

Let the summer play roll into school prep with joy and ease.

Wow, does time fly! I still remember those late summer days when my own kids were little—barefoot in the backyard, sticky from popsicles, and completely unaware that school was just around the corner. Now they’re all grown, but those memories stick with me, and so do the lessons I learned along the way.

Over the years—as a mom, nanny, and Montessori teacher—I’ve seen just how big the shift from summer freedom to school routines can be for toddlers. I’ve also learned that with a little preparation (and a lot of love), the transition can actually be exciting for everyone. So today, I’m sharing some of my favorite tips—things that worked for my family and for the many children I’ve cared for—to help make the move from summer fun to school days a smooth one.

1. Reestablish a Rhythm (But Keep It Light!)

One of the biggest lessons I’ve learned over the years? Routines are a toddler’s best friend. When my daughter was three, we would start preparing for school a couple of weeks in advance with a “practice morning.” We’d wake up, get dressed, pack a pretend lunch, and even have a “school circle time” in the living room. She loved pretending to be a student—and I secretly loved playing the teacher.

Ease your child back into a consistent sleep and wake schedule, but don’t feel pressure to make everything rigid. Use playful transitions—songs during toothbrushing, a morning “weather report” they get to announce, or letting them “pack” a backpack with their favorite book or stuffed animal.

2. Talk About What’s Coming

Toddlers thrive when they know what to expect. Instead of springing the idea of school on them the week before, start talking about it now. Frame it positively: “School is where you’ll get to paint, play, and make new friends.” When I was working with a family whose toddler was anxious about preschool, I used a feelings chart to help the child express what she was nervous about. That opened the door for her mom and I to gently reassure her and get her excited about what’s to come.

If your child is returning to the same school or care program, pull up pictures of last year. If it’s a new environment, take a drive by or explore their website together. Make the unknown feel familiar.

💡 A Quick Note About Pushback

And yes—some little ones might push back. It’s completely normal for toddlers to resist change or even feel anxious at the thought of going to school. I’ve seen it many times over the years, both in the classroom and with families I’ve supported. As a parent, it’s easy to feel discouraged or even take their outbursts personally—but I want to gently remind you: don’t. Take a deep breath, try to detach emotionally from the reaction, and focus on what your child is trying to communicate underneath it all. Acknowledge their feelings—“It sounds like you’re nervous about school”—and then offer something positive they can look forward to. Maybe it’s playing with new toys, meeting new friends, or even packing a special snack. That little shift can go a long way in helping them feel seen and safe.

3. Reinforce Independence with Purposeful Play

This is where my heart lights up—purposeful play is the perfect bridge between summer fun and school readiness. Over the years, I’ve helped children build independence through simple routines: putting on their own shoes, helping clean up toys, or choosing what to wear. These are skills that encourage confidence and reduce morning meltdowns once school begins.

One of my favorite activities to do with toddlers in late summer is what I call “Learning Stations at Home”—simple play zones that mimic school tasks. One corner might have crayons and paper, another has dress-up clothes for pretend social play, and another has puzzles or matching games. Kids feel like they’re still playing, but they’re actually prepping those little minds and muscles for what’s ahead.

3.5 Letting Them Choose (Within Reason)

It’s around this age that many toddlers start insisting on picking out their own clothes—and if that hasn’t happened yet, trust me, it’s coming! Even if your child isn’t showing signs of wanting this control right now, it’s a good idea to ease them into it over the next few weeks. Letting them choose between two or three weather-appropriate outfits can help them feel empowered without overwhelming them.

According to early childhood development experts, toddlers naturally begin asserting their independence between ages 2 and 4. It’s a normal and healthy part of development—part of what Dr. Maria Montessori referred to as the “sensitive period for independence.” Giving them small choices throughout the day (like what to wear) helps nurture decision-making and confidence.

Now, if your little one chooses shorts on a chilly morning or insists on wearing a superhero cape to school, don’t panic. Gently explain why certain choices may not be the best (“It’s too cold today for shorts, but you can wear this cozy outfit instead”). It may also help to rotate their wardrobe seasonally—put away summer clothes and make sure only fall-appropriate options are accessible. Fewer choices can mean fewer battles.

Remember, this is less about fashion and more about fostering a sense of autonomy. When children feel like they have a say in their day, they’re more likely to cooperate with the rest of the routine.

4. Acknowledge the Bittersweet

Back-to-school season can be emotional for all of us. My son used to cry the night before his first day—even in elementary school—because he missed summer adventures. I learned to acknowledge that feeling: “It’s okay to miss summer. I do too! But we can keep the fun going on the weekends. And I can’t wait to hear about your new class.”

It’s important to validate your toddler’s feelings while giving them a sense of excitement and reassurance.

5. You Don’t Have to Do It Alone

This transition isn’t just about the child—it’s about the whole family. If you’re feeling overwhelmed or unsure about how to help your toddler prepare, don’t hesitate to lean on support. Whether it’s through one of our Playtime Express in-home sessions or a quick chat with an early childhood expert, you’re not in this alone.

At Little Tot Depot, we specialize in creating intentional learning moments that meet children where they are. And as a fellow parent and teacher, I want you to know this: every little effort you make adds up. From one mom and educator to another—you’ve got this.

6. Prepare for Emotional Goodbyes

Drop-offs can be tough—for everyone. Whether it’s their first time heading to preschool or they’ve been in care before, some toddlers still struggle with saying goodbye, especially after a summer of togetherness. And let’s be honest—parents feel it, too.

A simple goodbye ritual goes a long way.

Here’s what I always tell families I work with: keep goodbyes short, sweet, and confident. Your calm presence helps your child feel secure. Try not to linger or sneak away. A simple routine—like a hug, a high-five, and a wave from the window—can offer comfort and predictability. If your little one cries or clings, that’s okay. It doesn’t mean you’ve done something wrong—it just means they love you and they’re adjusting.

Most children settle in within minutes of your departure. You can always check in with the teacher later for reassurance. Just remember, you’re planting the seeds of independence, and those roots grow deeper every day.

Warmly,

Ms. Buchi

Montessori Educator | Founder of Little Tot Depot