Fun Ways to Celebrate the Grandkids Going Back to School

Okay, I admit that I get a bit melancholy when my grandkids go back to school. I’ve had a great time all summer doing fun things and simply being together with them. Maybe it’s that I’m a little jealous that school will now claim more of their time than we get to spend together.

Yet, there are some good things too. The back-to-school season brings bouquets of freshly sharpened pencils (which I strangely love), new shoes, and the return of early mornings, and much-needed routines. But for us grandparents, it can also bring a little quiet after the whirlwind of summer fun. . .or chaos (as it is at my house all summer!)

However, all that doesn’t mean the connection has to fade with the summer sun! Whether your grandchildren live nearby or far away, there are many simple, fun ways to stay involved and make back-to-school time feel extra special. So, let’s celebrate!

Here are 10 creative ideas to try when your grandkids go back to school:

1. Send Some Snail Mail Encouragement

Kick off the school year with a little surprise in the mailbox! You can do this whether your grandkids live local or long distance. Kids really love to get snail mail!

Send a letter, postcard, or small care package during the first week of school. Include a short note of encouragement, a photo of you holding a “You’ve got this!” sign, or even a fun pencil or bookmark to make them smile.

*Long-distance tip: Aim for delivery mid-week to boost that mid-week energy!

2. Do a Back-to-School Interview

Start a yearly tradition! Ask your grandchild fun questions like:

• What are you most excited to learn?
• Who’s your teacher this year?
• What do you want to be when you grow up (this year)?

Record their answers on a printable interview sheet. It’s a great keepsake—and even better to look back on in a few years.

You could consider keeping these until high school graduation. Then put these all together for them in a book along with a picture of them from that school year. What a fun treasure that would be as they set off to begin adulthood. (Geez, I wish I had thought of this when my oldest grandchild was first starting school!)

3. Celebrate Small School Milestones

Celebrate those little (but mighty!) school wins. From their first spelling test to a successful presentation. Create a memory by making it a moment:

• Call or video chat to celebrate – Nothing says, “I really care about you and love you” like having someone recognize even the small things that you accomplish.
• Send a silly “You did it!” certificate – This does NOT have to be fancy or professional looking. Use a colorful marker, write “You did it!” in big bold letters, and add a few “Way to go!” or “Great job!” stickers. You will have something that is appreciated and personal to give them.
• Mail a small prize or treat – This can be delivered to their doorstep if you live close or mailed with the “You did it!” certificate from above. Make it a surprise because those are so special when you’re a kid.

4. Plan an After-School Surprise

Here’s another way to surprise your grandchild. If you’re close by, plan a surprise for after school:

• Show up at the bus stop with a favorite snack – If you’re grandkids ride a bus home, find out the bus schedule and meet your grandchild when he/she gets off the bus.
• Host a “Sundae Bar” at your house – This one is a treat for both you and your grandchild! Have ice cream and all the fixings ready to put together in an ooey, gooey mess at Nana’s.
• Drop off a backpack charm or mini treat at their home – Backpack charms can be purchased through Amazon, Walmart or you can make your own. A backpack charm, is really any little trinket that you can figure out how to attach to a keychain.

5. Play Back-to-School BINGO

• “I made a new friend”
• “I brought something home in my backpack”
• “I read out loud in class”

Mail it along with some dot markers or stickers. Offer a prize when they fill a row—or the whole card! However, you might want to require that they tell you about each thing that they crossed off in each square. This will give you a chance to connect with them and ask more about those things as the school year goes on.

6. Start a Homework Hotline

Let your grandchild know you’re available once a week (or once a month or anytime) as their go-to “homework helper” or just a friendly listener for school updates.

They can bounce ideas off you for a school project or just vent about math. Simply be there for them in any way you can. So, even if you don’t understand the math, your encouragement can mean the world.

7. Create a Study Buddy Box

Pack a box with a few school-year essentials—and a bit of grandparent magic:

• Fun pencils, sticky notes, or erasers – you can find so many fun options for any of these. You might want to try to find some that match your grandchild’s interests – Pokemon, unicorns, mermaids, superheroes, etc.
• A stress ball or small fidget toy – Some kids think better when they are moving their hands. It also can relieve the stress of beginning a new school year.
• A photo of you with a message like, “I’m cheering you on from here!” – I love the idea of taking a selfie and hold up the message you want your grandchild to see/hear. These can be silly photos so don’t worry about looking picture-perfect.

8. Send Lunchbox Notes from Nana

Lots of parents like to send lunchbox notes, but most grandparents don’t really get the chance. Perhaps you could send a batch of notes or jokes that a parent can slip into your grandchild’s lunchbox for you.

You could include silly puns, riddles, or quick love notes like:

“I donut know what I’d do without you!”
“You’re one smart cookie!”
(You could even send the “treat” with it.)

9. Plan an Afternoon of Fall Fun

Give your grandchildren something to look forward to after the first few weeks of school.  Plan a fun afternoon – something that you can do together. You don’t have to make this a big production. Keep it simple but plan to spend meaningful time together.

Plan a simple activity like:

• Apple picking
• Baking mini pies together
• A walk-and-talk nature scavenger hunt
• Or if your grandchild comes to your house after school on a regular basis, you could decorate a “homework station” at your house to make after-school time more fun.

10. Make a Back-to-School Time Capsule

If you’ve never done a time capsule before, you’re in for a treat. They really are simple and meaningful. This could be a fun activity to do on your last day of summer together.

To create a memory capsule together, get a large can with a lid or maybe just a plastic bag with a zipper closure. Or you could get really fancy and use one like this from Amazon. Label it, and then store it away until the last day of school.

You can start with items like:

• A photo of their first day in a new school outfit.
• A list of current favorites (song food, hobbies, etc.)
• A drawing (or impressions of) their teacher or classroom.
• A measurement of how tall they are.

When you open it on the last day of school, it will be so fun to see what’s changed (and what’s stayed the same).

What Will You Do to Celebrate With Your Grandkids as They Go Back to School?

Whether you’re near or far, these small gestures can make a big impact. Back-to-school season is more than just school supplies and new routines—it’s a fresh opportunity to build your grandparent-grandchild connection in thoughtful and meaningful ways.

Do you have your own back-to-school traditions with your grandkids? I’d love to hear them! Share your favorite ideas in the comments below.