A Sweet Send-Off to Summer (and Welcoming the School Year Ahead)

Easy, heartfelt traditions to celebrate the end of summer and the first day of school. Plus, the ones we're starting this year with our own family.

Aug 15, 2025

This year marks a big milestone for our family. Rory is starting kindergarten (😭), and Ellis is heading to preschool. Suddenly, school schedules and first-day photos are very much part of our lives.

We’ve always taken a first and last day of school picture, and last year I started a little video interview with Rory. I asked her things like her name, teacher, favorite color, and what she wants to be when she grows up. Those sweet little details I never want to forget. This year, we’ll be doing it again with both kids.

But beyond photos and interviews, I’ve been craving something a little more celebratory…a way to close out summer and kick off the school year with intention.

So I asked my community for ideas and wow… you delivered! Some of these had me crying. Others had me laughing. Most of them involve food. I’m obsessed.

Whether you’re sending a little one off to preschool or dropping your teen at high school, I hope these spark some inspiration for your own family.

End of Summer Traditions

We have an awesome ice cream spot near us called The Sugar Hole. A puppet gives you your ice cream, and the kids LOVE it!

There’s something special about closing out the summer with one final hurrah. From sweet send-offs to adventure-filled days, here are some reader-favorite ideas.

Make the Last Day Special

A picnic dinner on the school playground the night before school starts
A big beach day followed by dinner at the cabanas, blasting music on the drive home
Backyard camping the night before school starts
A “blowout day” or “Yes Day” where the kids choose the day’s activities and food (ice cream is always involved)
One-on-one “mom dates” before school starts
An “adventure day” on the last Friday of summer break
Roast s’mores and talk about what everyone’s looking forward to this school year
Visit as many parks as you can in one day (or adapt it to your city!)

Food-Centered Send-Offs

Ice cream the night before school starts
Dairy Queen runs on the last night of summer
“Sundae Sunday” with neighbors: build-your-own sundaes with all the toppings
Hibachi dinner the night before (a fun, celebratory spot that even teens still love)
Chinese takeout and labeling school supplies the night before
Root beer float night in the driveway with the whole neighborhood

"No one has to clean the house. There’s barely any cleanup. It’s the best kind of tradition."

Back-to-School Traditions

Whether it’s a calm morning or a big family breakfast, these ideas make the first day feel special for the kids and the grown-ups.

Capture the Moment

Growing up, we always took a picture with a thumbs up on our first day of school. We all even did it on our first day at college and with our first jobs! It was a tradition that lived on and on.

Classic first-day photos (front stoop, letter board, thumbs up!)
A quick video asking: “What’s your name? Grade? Teacher? What do you want to be when you grow up?”
A dry-run dress rehearsal the weekend before: photos, breakfast, no stress
Practice day with donuts and first-day outfits
Photos of your child walking into school with their grown-up

One story that brought me to tears:

“Two things I am so glad I did for back to school: 1) A photo of my son and husband, from behind, walking into school—every year from age 3 to 15. We had planned to do it through college, but my husband passed away suddenly when my son was 15. 2) A photo of my son in front of the school, against the bricks. It’s so powerful to see the growth, brick by brick.”

Start (and End) with a Treat

Our family’s Cowboy Chocolate Chip Cookies

Cinnamon sugar crescent rolls for breakfast
Chocolate chip muffins to start the day
Rainbow cake for post-school
Ice cream for breakfast on the first and last day of school
Waffles with any toppings they want
Pizza dinner after the first day
Make cookies together after school
Brownies waiting after school
Sundaes or root beer floats to celebrate the first day
Sugar cookies with school-color sprinkles on top!

"My mom always made us chocolate chip cookies and was home to greet us at the bus. Now I do the same for my kids."

Little Touches that Make a Big Impact

Sharpie heart drawn on your child’s palm for comfort during the day
A breakfast-to-go buffet on the front lawn for neighbors and friends
Parents meet for breakfast after drop-off
A “starting school” dinner party for all the kids going into kindergarten and their siblings

Our Family’s Traditions

So far, we’ve kept it simple:
✔️ First and last day photos with a letter board
✔️ Thumbs-up pose (just like my parents used to do with me)
✔️ A yearly video interview with questions about school and life right now

This year, I want to try something new. Maybe an end-of-summer “yes day” or ice cream the night before school starts. I love the idea of starting a tradition that grows with our kids.

Oh, and for the parents, tonight we are having our second annual back-to-school bar crawl. We rented a trolley for 24 of us and we’re having an end-of-summer hurrah!