Fresh Back To School Tips for Families With Preschoolers

It’s a brand new preschool year. That means new beginnings and new adventures! 

Starting a preschool routine can sometimes be a challenge, especially after a summer of late nights, camp outs & pool days.   Sandwich Montessori wants to help ease the overwhelming feeling to prepare you for this wonderful new adventure with your child.

We have 9 back-to-school tips for parents of preschoolers that will make the transition smoother and help kids have a positive experience!  Get ready to make some great preschool memories.

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TIP 1 – Introduce the idea of school early on.

TALK…

Build up the experience by talking about the exciting aspects of starting a new year.  The thought of new school supplies and new friends will help your little one look forward to the school year. Ask questions about anticipated classmates, teachers, activities, hopes, and even classroom decor. Share your own back to school tales with your little one.   Create a countdown calendar & mark off the days. Whatever you choose to incorporate, the weeks leading up to that first day offers meaningful opportunities to connect. It gives you the chance to discuss any worries they might have, as well as build enthusiasm. Listen to your preschooler and answer any questions or concerns.  Share insights into when you were in school and all the fun you had there.

READ… 

Read books about school with your child – it’s great bonding time, and often the books will spark a great discussion. Books are wonderful opportunities to create dialogue, address children’s fears, and establish some normalcy around going to school.  There are plenty of books about the first day of school and being away from parents. Be sure to add some of them to your current reading material. 

Or, you can make a book at home about the upcoming preschool experience your child is about to begin! Get creative, take photos of the school or of your child in front of school and add text like: “This is Olivia at school. This is her favorite t-shirt. This is Mommy picking up Olivia when school is over.” Make it personal, relatable and fun.

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TIP 2-Invest in a playgroup.

Research local groups & start getting involved in community events.  Exposing your child to other adults and children as early as possible with be extremely helpful.  Call the school and request a classroom list and email the parents to see if anyone wants to schedule a playdate or two before the school year officially kicks off.  If you don’t feel comfortable leaving your child alone quite yet for play dates, start by leaving them for short amounts of time with a close friend or relative while you run errands or enjoy a date night.    

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TIP 3 – Bath.  Story. Bedtime.

We all do much better when we have a routine.  Summertime schedules tend to be a little more flexible than school year schedules, and that’s okay- it’s vacation time! School days, however, will require early mornings and busy days, so establishing a routine early is important. Nobody likes to be rushed or unprepared, and getting used to getting up earlier will make everyone more comfortable when that first day arrives. Set your child up for success by helping them pick out their clothes the night before, pack their lunches with things they look forward to eating, and backpacks ready, will help the morning flow smoothly.  Start easing preschoolers into their new routine a few weeks leading up to the much anticipated first day.  

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TIP 4 – Meet & Greet.

Of all the back to school tips, this is one of the most important!

Even if this isn’t your child’s first school year, they will likely have a new teacher and a new classroom.  It is essential to check out the new classroom setting and meet the new teacher ahead of time since change can be scary. If there is an orientation or school visiting day, make sure you and your child attend.  A child familiarizing themselves with the space and the teachers ahead of time will help with the transition away from home-to-school. You can also ask how the teacher handles the first tear-filled days. How will the first week be structured to make the transition smooth for your child.

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TIP 5 – Encourage autonomy & bravery.

While no one expects a 4-year old to do everything on their own, age-appropriate independence is important.  Basic & age appropriate tasks allow children to learn how to take care of themselves. It gives them a sense of true accomplishment.  Some suggestions – cleaning up after themselves after meals, choosing clothes for the day, getting themselves dressed, buckling their seat belt, etc.  While it may be quicker and easier to do it yourself, it won’t help to make your child more self-sufficient. Resist doing for your children what they can do themselves.

Putting your preschooler in charge of a regular, simple task will build their confidence and sense of competency. Let them solve simple problems. If you see your child trying to assemble a toy or get a book from a shelf, pause before racing over to help; let them develop some problem solving skills. Assign a chore. A child who is entrusted to water the plants or empty the clothes dryer is likely to believe they can also get themselves dressed or pour their own cereal. Be sure the chore you assign is manageable and that it’s real work, not busywork, since even preschoolers know the difference. The goal is to make your child feel like a capable, contributing member of the family. 

TIP 6- Pull ups or underwear?

Now is probably a good time to consider potty-training if that hasn’t already been mastered.  You can talk about taking some big steps by starting preschool, getting bigger & learning new things.  Make a big deal about it! Take them to the store and let them pick out some super fun “big kid” underwear for when they go to school.  You know if your child is ready if they’re able to keep a dry diaper for 3-5 hours at a time, they begin to vocalize about going to the bathroom and do not like having a dirty diaper.  Feel it out. Start a few months before the beginning of the school year and have a plan in place, knowing the toilet routine and procedure at school so that you’re fully prepared no matter where they are at on the first day.  Keep trying. Keep encouraging. It’s a process. Be patient.    

TIP 7 – Remind them you WILL return.

You’ve just spent the whole summer together, and now it’s time to go your separate ways to work and school. Of course, it’s only for a few hours a day, but for a preschooler, this can seem like a lifetime.  Sometimes young children deal with separation anxiety. Honestly, some parents have trouble separating from their children too. In both cases, those feelings are totally normal! To make things easier on both of you, talk to your little one ahead of time. Let them know that you will be back to pick them up in just a few hours and remind them of all the fun they’re going to have with their friends and teachers.

It’s best to make the morning drop off quick so children can move on with their school day.  In the event that your child still holds some anxiety about school, and if you have a little one who cries when dropped off, rest assured that preschool staff will take care of your child.  This isn’t the first time. They have spent years training and preparing for all kinds of challenges, and they are likely pros at handling this and know how to walk them through a tough moment.  Of course love on your little one, but then move on quickly. Remember, while these steps kids take without us can be scary, going to preschool is one of many stepping stones helping to form our little people into who they are going to be.

TIP 8 – Shop for supplies together. 

Supplying your child with school gear they can enjoy will help get them excited about heading back to the classroom.  This experience is fun and creates a sense of excitement. Let them choose a backpack they love, their favorite snacks, and walk them through the supply list you received from the school. Talk about each item and what they will use them for at school.

You may have also received a list of items not to bring to school. Make sure you read the list thoroughly and cooperate with all classroom rules. 

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TIP 9 – Communication is key  (a comfort item is a bonus).

Children listen & understand a lot more than we give them credit for.  Going back to the first tip, talk about school. Talk about how they feel, their worries, their hopes & let them know you care by validating their feelings.  Comfort items can help reassure them during the transition period. If your child has a beloved teddy bear, blanket or “lovie” that they use for sleep and comfort, it may be worth packing in case of an emergency. You could also give your child something special of yours like a favorite scarf or bandana to reassure them that you will come back to get it.  Tracing your hand on a piece of paper & cutting it out and placing it in their bag, reminding them that if they get sad they can hold your hand.  

It is a lovely idea to leave notes, drawings, and even little painted rocks in random places to surprise your child. Sometimes in their lunches, and sometimes in their backpacks. This isn’t something to do just at the beginning of the year, and it’s not necessarily an everyday thing. But make a point to give them thoughtful reminders to let them know your heart is always there with them.


Working on smooth transitions is a process.  Planning & routine will help make the adjustment for all involved as peaceful as possible.  It takes time to feel comfortable in a new place with new people, but with these 9 valuable tips, you can support your child through being open, caring & motivating.  When you are positive and fearless, your preschooler will mirror your actions. Create a happy school scene & watch them thrive.

Don’t miss out on the benefits of a Montessori education for your child. Your child will gain unique learning experiences and big developmental strides at Sandwich Montessori.

  1. Your child will gain confidence with custom, hands-on learning.

  2. Your child can learn at their own pace, awakening their spirit, imagination, and passions.

  3. Your child learns cooperation and community with multi-age classrooms.

  4. Your child will develop a lifelong love of learning.

  5. Your child will learn independence.

  6. Your child will develop with the learning style that is best for them.

Come see if Sandwich Montessori is right for your family! Call us today to schedule a tour at 508-403-0118.