look who's going to preschool! GRAND ways to celebrate a Little's FIRST first day!
- Our Grand Lives
- Aug 28
- 11 min read
Updated: Sep 21
Thursday, August 28, 2025
We would be remiss
if we did not take a few moments at the beginning of today’s post
to acknowledge yesterday’s mass shooting at a Catholic school here in Minneapolis…
As retired teachers and grandparents, yesterday’s tragedy struck deeply! We each have spent our careers - our lives - guiding young children into nurturing spaces as they take their first steps into the world of learning. It’s heartbreaking to see that safety shattered in yet another senseless act.
Our prayers surround this school community - the students, families, educators and neighbors impacted. May God’s comfort and peace find every life touched by this unthinkable act.
Fall is beginning to show its presence here in Minnesota,
just as another school year begins!
As GRANDS, we feel the excitement right alongside our little ones,
watching them shoulder their backpacks and step into new adventures.
Whether it’s a FIRST first day or simply the next chapter,
this season reminds us all
how quickly they’re growing and how precious each milestone truly is!
In last week’s post,
we shared our tips for supporting the Littles in our lives
(and their families, too) as this new school year begins!
The teacher in each of us knows firsthand
how exciting, albeit stressful, a new school year can be
and, as GRANDS, we want to do all we can to help our loved ones navigate it all,
whether we live down the street or hours away!
Today, though, our post focuses on a slightly different topic,
although it definitely piggybacks on last week’s focus!
And we’re pretty excited about it!
There’s something extra special about a FIRST first day of school — the day a LIttle steps into preschool or kindergarten for the very first time. Backpacks look a little too big, shoes a little too shiny, and hearts (ours as much as theirs) feel stretched in brand-new ways. It’s a milestone wrapped in both joy and a bit of bittersweet, marking the start of so many adventures yet to come!
The FIRST first day feels momentous! It’s more than just the start of preschool or kindergarten, it’s the opening chapter of a child’s school journey. For us, as primary teachers, we've always known how these early steps shape a lifetime of learning and confidence. That tiny backpack carries not just crayons and snacks, but hope, curiosity, and the promise of so many new discoveries!
No wonder our hearts feel so full!
In honor of this special milestone,
in today’s post,
we take a look at some of the ways we GRANDS
- near or far -
can celebrate this FIRST first day with our Littles!
That very FIRST first day feels so big!
Over the years,
we’ve each seen hundreds of little ones
walk into school for the very first time!
But now, it’s our own grandchildren,
and the moment feels deeper and sweeter!
We know what awaits our Littles
— friendships, songs, discoveries —
and we’re so excited to watch this new chapter of their story begin!
Laurie’s four-year-old Little D is headed to pre-K this year
and Laura’s three-year-old Little L is headed to preschool!
For each of us, two of our greatest passions
- our Littles and learning -
are coming together!
And, of course, just as we did last week,
we can’t help but continue our trip down memory lane…
How did these two grow into preschoolers so quickly?
And, more surprisingly,
how are these two their mamas???
We can’t help but recall our own firstborns’ first days of school,
their small hands clutching ours and their brave smiles hiding just a hint of nerves!
The saying is true… TIME CAN BE A THIEF!
And sometimes it’s more apparent than others!
YEP! We’re a wee bit excited!
And, of course, we’ve been thinking about a special way to mark these occasions!
Creating a new school year tradition with your Littles is a beautiful way to mark the passing of time and remind them that their journey matters. Traditions, even the simplest ones—a special breakfast, a yearly photo on the front step, a quick phone call, or a prayer together — give Littles a sense of stability and belonging. They show our Littles that we see them, we celebrate them, and we’re cheering them on as they grow. For GRANDS, like us, it’s also a chance to stay connected and weave ourselves into the fabric of their everyday story, even when from a distance!
As we mentioned above, last week’s post holds several ideas
for celebrating a new school year with your Littles,
including a few thoughts for yearly traditions to share together,
like Giving Back, Going on a Date or A First Day Surprise!
You can find more details about each here!
In addition, here are a few other special ways we’ve celebrated
a FIRST first day with special Littles in our lives!
Sneaky Yard Decor!
First up, Laurie is sharing a Back to School tradition
that first began for her in the fall of 2020!
As you can probably imagine, kindergarten has always held a special place in my heart! It’s such an important beginning! My oldest great-niece started kindergarten in 2020 - during the pandemic, and there wasn’t much I could do to celebrate with her. So I decided to give her a memorable send off on her first day of school!
I purchased a set of large pinwheel flowers from Amazon and some other fun signs and streamers. The night before school started, my husband and I snuck over in the dark and decorated her front yard to surprise her! The next morning we received many pictures of a happy and excited kindergartner, heading off to school knowing she was loved and cherished by many people… including her great aunt and uncle!
Then in 2022 and again in 2023, we repeated our sneaky yard decorating tradition for our next two great-nephews!
There’s many decorations you can make yourself out of tagboard and markers. You can also use ribbons or crepe paper to tie in trees or bushes.
DISTANT GRANDS… If interested, you could enlist the help of the parents to place the decorations you've planned or prepped and sent in the yard for you!
Don’t be surprised if this tradition continues
when our Little D heads off to kindergarten in...
oh my goodness, only one year from now!
A Yummy Treat!!
Laurie’s sister has her own special way
of celebrating the first day of school with her Littles…
A tradition that’s longstanding!
My sister has always baked chocolate chip cookies for her own children on the first day of school. She was a working mom and would take a vacation day so she could make cookies and be ready when her Littles got home from school that day! This tradition continued through college! She would bake cookies and send the cookies off with them as they headed back to school.
These days, my sister is lucky to live fairly close to her grandchildren and, so, the tradition continues! She always makes it over on the first day of school with freshly baked chocolate chip cookies. Now that shows a grandma’s love, for sure!
DISTANT GRANDS… You can send your own home-baked goodies to your Littles on their first day by sending a special care package their way!
Such a simple tradition but one everyone looks forward to each year! I benefited from many of those “first day of school” cookies when I was teaching, and there is nothing like a yummy, gooey cookie waiting for you at the end of that first BIG day!
Class of 20__!
When special Littles in Laura’s life head off to their FIRST first day,
here’s how she celebrates the occasion!
This option I chose for a special Little in my life two years ago - my grand-nephew who started kindergarten that year and will graduate in 2036!
Each year, either on the first (or perhaps the last day of school)l, take a photo of your Little in his/her T-shirt. With one initial investment, this memento will have a lasting impact! Just imagine what a great collage all these photos will make at your Little’s graduation party some day!
DISTANT GRANDS… This would be an easy gift for you to send, right? Include a special note, letting your Little know how excited you are to watch them grow and learn in the years to come!
More Traditions to Consider!
We’re busy thinking about what traditions we’ll begin this year with our own sweet Littles when they head to preschool in mid September and which idea(s) we’ll save for the start of kindergarten! Here are a few more possibilities that are on our radar:
Choose a New Book to Mark the Occasion!
There are so many children’s books out there that celebrate the new school year! Look at all these options we found during a recent trip to Barnes & Noble!
Be sure to add an inscription in any book you purchase with a personal message, including the year and the grade! You may even want to add a special “date” as part of the experience… just like Little D and her dad had recently!
Make a First Day Video for Your Little!
Your Littles will love it if you send an annual greeting via text, voice messaging or by attaching a personal video to a text or email! This is a fabulous way for GRANDS to connect with Littles and works especially well for Distant Grands!
Don’t have the ability to create a video or record a voice message? No worries! Many Littles are utterly thrilled when they find such a treasure addressed to them and waiting in the mailbox!
Go Back to School Shopping Together!
Laurie enjoyed a day of shopping with Little D and they picked out a Back to School outfit or two!
Then Little D had more fun showing mommy what was picked out!
Meanwhile Distant Grand, Laura, may have made a few online purchases of her own that will soon arrive on Little L’s doorstep! Hopefully, we’ll have our own version of Show & Tell via FaceTime soon after!
Plan an Annual Meal OR Dessert to Celebrate!
Host a Back to School dinner or breakfast the week before school begins or during the weekend that follows. This annual tradition can include your Littles’ favorite dishes and would be a great way to hear all about their hopes and dreams for the year or as a way to review their first week adventures!
Laurie made a special dessert for her family each year to celebrate the first day of school! Her annual Bus Cake made its first appearance when her Daughter A was in kindergarten and this tradition continued every year after!
Now it’s Daughter A’s turn to continue this tradition…
Sssshhh!
She’s planning to start their own family Bus Cake tradition with Little D!
In addition to the traditions we establish
as our Littles begin this exciting new journey,
there are a few practical ways we can help bridge this transition,
especially when it comes to preparing for that FIRST first day!
#1 - Preview! Preview! Preview!
Young children benefit from previewing experiences like talking things through, practicing or role-playing before something new happens! How do you say “hi” to a new friend, what to do if you need to use the bathroom, wanting to play with a toy that someone else is playing with are all examples of such situations and these conversations can take place at the beginning of the year as well as throughout the school year!
Since Laurie lives nearby and will still be watching Little D one day a week, she plans to tape copies of Little D’s classroom calendar as well as the monthly breakfast and snack menus inside her kitchen cupboard (with Mom's permission, of course). That way, she and Little D can refer to these often... and preview away!
So smart!
Providing experiences for your Little to preview reduces their anxiety, builds confidence, encourages independence and deepens trust!
#2 - Tell Stories!
Telling related stories is a powerful way to help Littles cope with new situations! When children hear about characters - or even their parents or grandparents - going through something similar, it normalizes their own feelings of worry or excitement!
When Laura’s daughters were young, she’d tell them Laura Stories,
all retellings of events from her own childhood!
They would ask for these stories repeatedly over the years!
Now, a new generation gets to hear those tales!
During the last few weeks, Laurie has been telling Little D
stories of her own kindergarten experience
as well as from her mom’s (Daughter A’s) childhood!
Stories give our Littles a safe way to imagine what might happen, see problems solved, and realize that they, too, can be brave and capable!
#3 - Remember Your Role as a GRAND!
As GRANDs, one of the best ways we can support parents of a brand-new preschooler or kindergartner is simply to be available, as needed, during this big transition. The FIRST first day of school isn’t just a milestone for your Little - it’s a big step for mom and dad, too! We can encourage them with gentle words of reassurance, offer practical help that lightens their load, and celebrate this moment so they feel confident in their role as parent!
By respecting the parents’ routines and choices, and perhaps starting a small GRAND tradition of our own, we can (hopefully) become a steady source of comfort for everyone involved. It’s important to remember that it's not our place to take over, but rather, it's to cheer them on, reminding them they’re doing a wonderful job raising a little one who is ready to take these first brave steps.
As always, THANK YOU for taking the time
If you’d like to follow us on Instagram or Facebook,
You can also subscribe to our site if you’d like!
By doing so, you’ll only receive an email whenever a new post is published!
We’ll be back TOMORROW with our review of the past month!
Please join us as we reflect on the month of August and bid it adieu!
A GRAND’s heart holds two stories at once.
As we watch our Littles step into school for the very first time,
we can’t help but see our other little ones from long ago.
filled with hopes and dreams of their own!
It’s a sweet reminder that time circles back,
that love multiplies,
and that every first day is both a continuation and a brand-new beginning!
SPECIAL THANKS TO THE FOLLOWING SITES FOR FEATURING OUR POST!
Senior Salon Pit Stop from Scratch Made Food for Hungry People
You are the Star from At Home with Lisa
You are the Star from Kris & Larry
You are the Star from Moms are Frugal
You are the Star from Dolly Dowsie
Thank you for featuring this post on your sites!
❤ We love our blogging community! ❤
💗 We are delighted to join the following link up parties and blog hops! 💗
MONTHLY
SUNDAY
MONDAY
TUESDAY
WEDNESDAY
THURSDAY
FRIDAY
SATURDAY
How exciting! Have fun in Pre-K little ladies.
Thanks so much for sharing with Sweet Tea & Friends Ladies. I'm so happy you're here.
xo
This is just so sweet! Such a great thing to celebrate, and I especially love the ideas for distant Grands. Thanks for sharing this post with all of us at the Will Blog for Comments #68 linkup. See you next week at #69. Hope you have a great week.
Aw, I hope Little D and Little L had the best first day. What little cuties. The baked cookies are such a lovely tradition! Yummy.
Thinking of all those poor people impacted by that awful shooting. So terribly sad.
Putting up a sign in the middle of the night for the little one to pose around is such a cute idea! There really are so many cute ideas in here. Thank you for supporting Weekend Traffic Jam Reboot each week as well!
It makes me so sad that shootings in school still happen.
Aww! Such an exciting time for so many little one's, the first day of school! I hope all your grands have a fab school year! What fantastic ways to celebrate!