Tips to Start Your Own Cookie Day

Note from Casey: I hope everyone had a wonderful Thanksgiving weekend. Now, it’s full steam ahead for the holidays around here. Today, the “Queen of Christmas”, my mom, Jan, is taking over the blog to share more about our annual Cookie Day tradition. It’s a very special part of our family history and I hope you can create your own version of Cookie Day!

What Is Cookie Day?

Tips to start your own cookie day

Cookie Day is probably my favorite yearly tradition. It’s a tradition that was started by my own grandmother when my oldest son, Harry, was little. Since then, almost 40 years ago, we have refined the tradition and made it work for our family and friends. That’s the thing with traditions – they can grow and change and develop into whatever suits your family and your situation. In case you missed it, I wrote a blog post all about starting your own family traditions right here.

Essentially, Cookie Day is a time to gather to bake and decorate cookies with our favorite people. Today’s post is all about the O’Halloran Cookie Day tradition, but I hope this will give you permission to start or refine your own tradition. Let’s make some memories!

How Cookie Day Began

When my oldest, Harry, was about two years old and we visited my family for Christmas, my Grama spent one afternoon making sugar cookies with Harry right by her side. I might have helped a little bit that year, but really, it was an afternoon of fun for Grama and Harry, with the rolling, cutting, baking, and decorating of the cookies. When the sugar cookies were made, my Grama added many other kinds of Christmas cookies that she had previously baked and frozen, and we made plates and plates of cookies to take to neighbors and friends.

My Grama grew up and raised her family in western Kansas, with very little money. Plates of cookies, beautifully displayed and wrapped with foil and a pretty bow, were the gifts that she could afford to give to the meaningful people in her life.

Over the next couple of years, we continued to do the same thing as my other children were born and started participating with my Grama. And by then, I was paying more attention and helping out with all of the baking and decorating.

Cookie Day – As The Kids Grew Up

When Casey was almost two years old, my Grama died and this Cookie Day tradition could have been lost without her. That’s the year that I decided that I would keep the tradition going and refine it to make it work for my family.

Cookie Day in the 1990s
My kids and my mom, Meme

It started slowly, with each of my children inviting a friend over for the day to help make and decorate a few kinds of cookies. They were all young then, so it was messy but exciting, and everyone got to take home a plate of cookies for their family – our Christmas gift to them.

Delicious chocolate chip cowboy cookies
Our Famous Cowboy Cookies

We would bake just two or three types of cookies on the actual Cookie Day and they were the “fun ones” (like sugar cookies and peanut butter cookies) that the kids enjoyed decorating. But in order to have a nice, big variety for everyone to take home, I would make five or six different recipes earlier and keep them in my freezer. At the end of the day, I would get all the cookies out of the freezer and encourage everyone to load their plates with some of each kind. Also, I have always liked to include a cookie Christmas ornament for the guests to take home and remember our day.

cookie day 2017
Cookie Day – 2017

As time went on and the kids got older – in college and in their twenties – they had more friends to invite. During those years, Cookie Day turned into a day-long pre-Christmas party, complete with sandwiches for lunch, pizza for dinner, and a bar full of beverages.

Many of the participants, including some of my own children, participated much more in the merriment and much less in the actual cookie-making. Luckily for me, there were always some guests who were interested in baking. I would grab onto those guests and keep them busy all day long!

Cookie Day 2019
Cookie Day – 2019

These were years of cookie-making with young adults who didn’t yet have children, and the size of the group started getting a bit out of control. I think we had over 60 people at our largest gathering!

Gradually, my children and their friends started getting married and having children of their own and our Cookie Day changed again. Once again, the young children were sitting at the table, decorating sugar cookies, and their parents were helping with the mixing and the rolling.

Cookie Day – Now

How to prepare now for the holidays

When the pandemic hit, Cookie Day was pared back even more and it became exactly what it had been in the beginning – a day of cookie-making fun for Grama, parents, and grandkids. We went from a giant party of friends back to a family celebration, but it was nice because the craziness was gone, and we were able to enjoy our time together as a family.

Creating our own cookie day celebration

This year, Casey and Finn will be hosting Cookie Day (this weekend) and we have decided that each family will invite another family for the day. That means the grandkids will have a few friends and cousins helping with the baking and decorating, but the group will be very manageable.

My Best Tips to Create Your Own Cookie Day Tradition

my best tips to start your own cookie day

As you can tell, our tradition of Cookie Day has changed over the years, but it has never been lost. We keep adapting and making it work for our family and friends. If you would like to start a similar Cookie Day tradition in your family, here are some of my best tips.

  • Put the date on the calendar many months ahead of time so everyone is available.
  • Gather your ingredients early and start baking and freezing cookies a month or so in advance.
jan and her baggie of dry ingredients
  • Some years, I gather everything I need and then measure all of the dry ingredients (flour, sugar, oatmeal, nuts, etc.) and put them together in baggies for each recipe. That way, when I am ready to mix, my measuring is already done and all I have to do is dump each ingredient in the bowl and start mixing.
  • Find inexpensive Christmas platters at the grocery store right after Halloween.
  • Pick only two or three types of “fun” cookies to make on Cookie Day.
  • Order ornaments early to attach to the platters of cookies. Here are the ornaments I chose for this year.
  • Expect a giant mess, with frosting and sprinkles all over, but memories to last a lifetime!

Our Family’s Favorite Cookie Recipes

Our Cookie day tradition

Casey has shared many of our family cookie recipes here on the blog. I hope you’ll find a few new ones to add to your own holiday baking this year.

You can find our family sugar cookie recipe in Casey’s holiday gift guide right here!

Do You Have a Similar Tradition?

My mom shares her favorite tips to start your own cookie day

Do you have a similar Cookie Day tradition in your family? Or maybe a Cookie Exchange? If so, I would love to hear about your traditions…


The Year of Casey

Hey there!

I’m Casey Finn, the voice behind The DIY Playbook. I’m a Chicago gal teaching you how to design, DIY, and maintain your home…by yourself! Learn more about me right here.