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A delicious and festive cookie dessert box with gingerbread men, stockings, and sweaters decorated with chocolate, Chewy maple cinnamon cookies with white chocolate, Brown butter and maple chewy pumpkin cookies, Chocolate covered Oreos, Chewy Oreo Brownies, and Gingerbread Crinkle Cookies

Delicious Christmas Cookie Box Ideas

I hope these festive and delicious Christmas Cookie box ideas inspire you to make your own dessert box this year! It isn’t as intimidating as it seems. With steps such as freezing some of your cookies ahead of time, pre-selecting the size of your box, and making a sketch of your design, you can take loads of pressure off while saving time!

This holiday cookie box features:

  • Soft gingerbread men, stockings, and sweaters decorated with chocolate
  • Chewy maple cinnamon cookies with white chocolate
  • Brown butter and maple chewy pumpkin cookies
  • Chocolate covered Oreos
  • Chewy Peppermint Oreo Brownies
  • Gingerbread Crinkle Cookies

On this page, you fill find links to my favorite holiday cookie and dessert recipes shown in the photos, tips and tricks for how to design and structure your box, as well as cookie decorating inspiration! You’ll also find tips on making these cookies into gift boxes at the bottom of the post, if you’re giving the treats away on a smaller scale.

A delicious and festive cookie dessert box with gingerbread men, stockings, and sweaters decorated with chocolate, Chewy maple cinnamon cookies with white chocolate, Brown butter and maple chewy pumpkin cookies, Chocolate covered Oreos, Chewy Oreo Brownies, and Gingerbread Crinkle Cookies

How to plan your Christmas Cookie Box:

A lot of brainstorming goes into creating a cookie box, whether large or small. Taking some of the preliminary steps below will help ease the stress of trying to bake and assemble the box at once.

  1. First, select your cookie box.
    1. Deciding on your box first will greatly help determine how many cookies and treats you will need to make, as well as how many can fit. 
    2. If you can find a box that has a bit of depth and some built-in dividers, that is best case scenario! 
    3. The cookie box pictured is from Michaels. They had a few designs over the holiday season to choose from. You could always buy one and repaint it to fit the season’s colors.
  2. Select how many cookies and desserts you want to include and test them ahead of time.
    1. As I was brainstorming ideas, I did trial runs of recipes I hadn’t made before to ensure they would turn out, and decide if they needed tweaking or shouldn’t be included at all.
  3. Freeze some of your desserts ahead of time. 
    1. If you know a certain cookie or dessert freezes well, make it ahead of time to save yourself from baking like crazy right before you want to serve the cookie box. 
A partially full holiday cookie box filled with brown shredded filler paper, some gingerbread men, gingerbread stockings, and Oreo brownies

How to design and organize your cookie box:

  1. Vary the dessert sizes, textures, and colors.
    1. This adds visual interest and provides flavor variety for the recipients. 
    2. Hang candy canes over the edge of the box, and sprinkle festive candy throughout for pops of color! 
  2. Make a sketch of your cookie board layout.
    1. I found it extremely helpful to make a drawing of my cookie box and plan which items should go where before actually placing them in the box.
    2. Making a sketch saves time, minimizes cookie breakage from moving them over and over, and allows you to strategically vary the sizes and colors of which treats will be next to each other.

What can I use as dividers and filler for my holiday cookie box?

This is where you can get creative! 

  • Parchment paper is your best friend.
    • Use white and brown parchment paper to protect the cookies, add texture, and even act as a wall between goodies.
  • Use shredded paper to help fill the box and give the cookies a “lift.”
    • Adding shredded paper helps give volume to the box and pushes the cookies up higher, so you don’t need to stack as many to make the box appear full.
    • It also comes in a variety of colors! 
  • The best hack of all – use cardboard mini loaf pans as separators!
    • These mini loaf pans were the most convenient find! I saw them at Target and had no clue they would end up being the perfect box dividers.
    • Keep them whole, or cut some of the sides off to create thin, streamline cookie separators.
    • The pans aren’t currently on Target’s site since they are seasonal, but they were called –  4” x 2” 6pk Paper Oven Safe Mini Loaf Pans – Welcome Home Brands.
    • These pans are very similar on Amazon.

Details for the desserts included in the Christmas cookie box:

overhead shot of peppermint oreo brownies decorated with festive red creme filled oreos on top, with a brown backdrop and red string and candy canes surrounding them

The festive Oreo brownies:

Recipe by Baker by Nature

This is my ultimate, holy grail brownie recipe. It is easy to make, chewy, fudgy, and has a crunch from the Oreos and chocolate chips. I cannot speak highly enough of these. They are even terrific straight from the freezer – they stay chewy and the chocolate chips add even more crunch and texture.

How to make a peppermint version:

  • Substitute 1/2 tsp peppermint extract for vanilla extract and use only 1 1/2 tsp vanilla.
  • Use green mint baking chips (linked here are the ones I used by Guittard) along with semi-sweet chips. I used equal amounts of each to make the full 3/4 cup required.

Check out my detailed post here for a Halloween version of the brownies! 

The gingerbread men, stockings, and sweaters decorated with chocolate:

Full post on how to make these linked here

If you like standard gingerbread men cookies, you will absolutely LOVE the combination of the soft, chewy, and spicy cookie with sweet and creamy white and dark chocolate. The way the chocolate melds with the perfectly soft and spiced cookie is a delicious flavor and texture experience, especially if you add sprinkles or the crushed candy canes! 


A delicious and festive cookie dessert box with gingerbread men, stockings, and sweaters decorated with chocolate, Chewy maple cinnamon cookies with white chocolate, Brown butter and maple chewy pumpkin cookies, Chocolate covered Oreos, Chewy Oreo Brownies, and Gingerbread Crinkle Cookies

The gingerbread crinkle cookies: 

Recipe by Two Sisters Crafting.

These crinkle cookies are soft, fudgy, and have the perfect amount of spice. While I absolutely adored them, I had no idea they would become a top-ranking favorite of my friends and family! Even people that said they disliked gingerbread loved them – that is always the true sign of a successful cookie and recipe!


Maple cinnamon cookies half dipped in white chocolate, drizzled with white chocolate, and decorated with holly berry sprinkles on a parchment lined baking sheet

The chewy maple cinnamon cookies dipped in white chocolate:

Full post with details linked here.

These are cookies that make you feel cozy as soon as you take a bite. With maple extract and syrup, they have a warm flavor unlike any other cookie I have made. They are also super soft and chewy. By dipping and drizzling them with white chocolate, and adding holly berry sprinkles, you now have a cookie that is equally as beautiful as it is delicious!


Brown Butter and maple chewy pumpkin cookies topped with flaky sea salt surrounded by cinnamon sticks, pinecones and a small pumpkin

The brown butter and maple chewy pumpkin cookies:

Recipe linked here by Butternut Bakery. 

These cookies completely embody the essence of this cozy season. Even better, they’re chewy (chewy cookies > cake cookies) and predominantly taste like spices and maple, so they’ll go over well even for those that don’t get on the pumpkin train! They also freeze well and are a good option to make ahead of time. 


Overhead image of festive chocolate covered oreos in the design of snowmen with mini carrot noses and M&M ear muffs, white chocolate polar bears with a brown snout, chocolate ornaments, and half dipped oreos with a green tree design on top.

The chocolate covered Oreos:

These cookies are delicious, fun to make, and no oven is required – what could be better! Check out my full post linked here for more details of how to make them.


Not making a dessert board? Package the cookies up in pretty gift boxes!

A delicious and thoughtful cookie box is always such a fantastic gift to give, and receive! I found these festive tins at Michaels and absolutely loved that they came with a clear window that shows a sneak peek of the contents.

If all of your cookies don’t fit in one tin, add another box on top and secure them with a ribbon and gift tag!

Add a personal touch to the cookie gift box:

  • I added a fun blown glass ornament to each box that reflected part of the recipient’s interests. Some included glass ornaments in the shape of taco trucks for Mexican food lovers, kayaks for water activity enthusiasts, a 6-pack of beer for the boozy beverage fans, and pizza for…well…just about anyone! A part of the gift that will stand the test of time once the cookies are all eaten up.
  • Stores that have unique and fun glass ornaments like this are Target, Michaels, World Market, and Hobby Lobby to name a few!

Pin for later!

If you make this dessert or have any questions, please leave a comment below! I absolutely love hearing when others are inspired to step into their kitchen and try out something new.

Happy Baking!

XOXO,

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