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Back to School Traditions Your Kids Will Love

Monday, August 21, 2017

back to school traditions

‘Tis the season, folks! Back to school! 

Being a teacher, back to school looks a little different in this house than most. While most parents are silently (some not so silently) celebrating the return of a clean house, a routine, and a little peace and quiet–the Pennington house is the definition of hot flipping mess! Papers, planners, lamination, scissors, markers, and tiny scraps of paper are EVERYWHERE! It can be overwhelming for everyone in this house,  to say the least.

Going back to school is a time of mass chaos for my kiddos, and it is a big deal for all kids! Starting a new grade, seeing old friends, meeting new people, getting back into a routine after the lazy days of summer–it’s all so exciting and even a tad nerve wracking for our small people. That’s why I like to take a little time out of my busy back to school prep to focus on my little guys each year.

Back to School Date Days

Every year since the boys have started school, we’ve had a tradition that we all love. Each of my sons has his own one on one “date” day with Mom. This also means brother is getting in some great bonding time with Dad! My boys are polar opposites so, naturally, they’re not into the same things at all. Giving them one on one time allows them a full day focused around things they love without compromising for the sake of a sibling!


We have some traditions that we commit to every year on date day! For starters, we head to our favorite outdoor mall and take the obligatory posed photo to show how much they’ve grown. Y’all–these boys did some serious growing this past year! No wonder my grocery bill was astronomical!

Back to school traditions

Boys Love to EAT

Obviously. Just look at those two! If I’m being honest here, most of our date days revolve around food. We start our day with lunch each year. This year we finally took the advice of one of my good friends and hit up an adorable little diner. Thing One loved Cindy’s Diner so much that his brother begged to go there on his date day! I let them order anything they wish on date day–which includes root beer floats!

back to school              

We also make an annual stop at a local gourmet popcorn shop, as well as DeBrand for some yummy gourmet chocolate! (Then we brush our teeth REALLY well to avoid an astronomical dental bill!)

back to school traditions           

New Clothes

I remember going clothes shopping with my mom at the start of each school year. It was always so fun and exciting–until October when nothing fit. For this reason, I don’t usually buy the boys a heaping pile of new clothing all at once. I do take them to pick out a first day of school outfit, though. I love seeing their unique styles come through.

The Book Store

Being the nerdy reading teacher that I am, we never go to the mall without hitting up a book store. On date day, the boys each get to pick out some new reading material. I love that this year they both picked a ton of information texts! Max sat down with this How to do Everything book and read it in two days! Charlie, meanwhile, is learning about Pearl Harbor and The Superbowl!

back to school books

The Big Surprise

After we hit up all our favorite traditional date day stops, I surprise the boys with an activity I think they’ll enjoy. We’ve done things like SkyZone, Chuck E. Cheese, and Putt-Putt Golf in the past. This year I had big plans of taking Max to the Fort Wayne Art Museum, but it was closed that day. Instead, seeing The Nut Job 2 in 3D made him pretty happy! Going at 2pm meant we had the whole enormous theater to ourselves, which was pretty awesome!

back to school movie

Charlie’s big surprise was a visit to Painting Fun Spot! He picked out a pretty cool ceramic car that he decked out with a custom paint job!

Here’sback to school art

All’s Well That Ends Well

At the end of each of their date days, both boys are always full of smiles, hugs, and gratitude. Mama goes to bed with a full and happy heart those nights. And the classroom prep mess is looked over until the next day when chaos ensues again!

Here’s to a Happy Back to School Season!



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  1. Luisa says:

    Aww I miss all those back to school rituals. It’s such an exciting time. Have a great start to the year!

  2. Familyearthtrek says:

    They do grow up!
    You dont notice it as parents but that is a fun way to mesure them!😊 To be honest, I have been 24/24hours with my daughter ever aince she was born so I am just will be happy the day she is out of the house to school!😂 (But at the same time I cant let her go my baby girl)

  3. Mary says:

    This is so fun! I love the root beer floats. So many sweet memories for your kids. You are a good Mama!! 🙂

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