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I’m excited to share my 2019 Holiday Cookie Box…along with some tips and tricks to help you create the perfect cookie box at home! This year’s box is filled to the top with all our most favorite Christmas cookies and bars. There’s everything from caramel snickerdoodles, to old school pecan cookies, to milk chocolate brownies, and more. We’re packing up only the very BEST cookies and sweets this holiday season. Anyone you gift this box to is going to love you just that much more. Trust me, there is no better gift than a box full of homemade cookies.

overhead photo of 2019 Holiday Cookie Box

Pausing our usual Favorites post…just this week, to share my holiday cookie box. I know many of you really look forward to the Favorites post so, but I promise, today’s post is worth it…because it’s the sweetest day of the year here on HBH! I could not be more excited to share this year’s cookie box. Without a doubt, this is my favorite box yet (see year one and year two), as I have filled it to the brim with my favorite cookies.

The last two weeks have been nothing but cooking and baking in prep for my trip to NYC this week. I turned out a whole lot of sweets this weekend to get this year’s box ready for you all. Many of you have been asking for me to share my box earlier this year, so I wanted to get this post up as soon as possible.

I am so happy you are all excited to gift friends and family cookies this holiday season!! One of my favorite Christmas traditions is shipping out Christmas cookie boxes to friends and family. I know things are BUSY this time of year, but I try to make an effort every year to set aside one day for Christmas cookie baking. We’ve been doing this for a few years now and it’s become one of my favorite December activities.

So with that, let’s jump right in and talk about all the steps you’ll need to take to create the perfect box. ‘

overhead photo of 2019 Holiday Cookies all together on table before adding to box

Step One: Choose Your Cookies

When choosing your cookies, be sure to pick cookies, and or other desserts, that will hold up well in shipping. I like to choose cookies that are different shapes and sizes. I find it’s nice to have a little variety in the box, so I’ll normally bake anywhere from four to six different cookies and then divide them between boxes.

Here are the cookies used in my 2019 cookie Box:

Salted Caramel Pretzel Snickerdoodles | halfbakedharvest.com #cookies #snickerdoodles #christmas

Salted Caramel Pretzel Snickerdoodles

Slice n Bake Salted Chocolate Butter Pecan Cookies | halfbakedharvest.com #cookies #christmas #thanksgiving #chocolate

Slice n’ Bake Salted Chocolate Butter Pecan Cookies

Salted Milk Chocolate and Peanut Butter Blondies | halfbakedharvest.com @hbharvest

Milk Chocolate and Peanut Butter Blondies (oldie but goodie HBH recipe

Chewy Chocolate Ginger Molasses Cookies | halfbakedharvest.com @hbharvest

Chewy Ginger Molasses Cookies

Holly Jolly Santa Cookies | halfbakedharvest.com #santacookies #sugarcookies

Holly Jolly Santa Cookies

Homemade Holidays- Coconut Caramel Stuffed Chocolate Covered Pretzel Presents | halfbakedharvest.com @hbharvest

Coconut Caramel Stuffed Chocolate Covered Pretzel Presents (throwing it way back to the early days with this recipe)

Vanilla Wreath Cookies | halfbakedharvest.com #cookies #Christmas #easyrecipes

Vanilla Ginger Shortbread Wreaths

milk chocolate brownies

Milk Chocolate Peanut Truffle Brownies (another oldie but goodie)

Step Two: Get a Sturdy Box

The box you use to package your cookies is very important. You’ll want to choose a sturdy box that can handle shipping. I love using a heavy-duty cardboard box, think something like a nice hatbox. Then I like to add cardboard ornament dividers. Or simply make your own out of cardboard from old Amazon packages. Dividers keep each cookie separate from one other. If you’re looking to buy a box, I’d recommend something like this and either adding dividers or using tissue paper between each cookie.

Alternately, you can use cookie tins as well. I love these festive square tins or these more classic round tins.

Tip: place bubble wrap in the bottom of your box, then line the box with a very large piece of plastic wrap (use multiple layers if needed) that will be large enough to wrap overtop of the cookies when the box is full. This keeps the cookies safe and fresh.

close up photo of holly jolly santa cookie

Step Three: Gather Cute Packaging and Ribbon

I try to find festive plastic wrapping, food-safe tissue paper, and or ribbon, to wrap around my cookies. This gives your box that extra special touch.

Tip: I always wrap cookies that I want to stay extra fresh in holiday ziplock storage bags and then add them to the box. If you want to use something a little cuter than storage bags or plastic wrap, try using holiday cellophane bags that can be sealed with ribbon, small holiday cookie tins or boxes or food containers that will fit inside your box.

close up photo of cookie box

Step Four: Bake The Cookies

I like to bake and decorate the cookies in the morning, then let them chill and package them up late afternoon or at night so that they are ready to ship in the morning. Have fun and make a day of this with your girlfriends, kids, siblings, really anyone who loves to bake and listen to Christmas music!

overhead photo of 2019 Holiday Cookie Box

Step Five: Package Everything Up

Packing up your boxes is probably one of the trickiest steps of sending out holiday cookie boxes. You’ll want to make sure that all the time you spent making cookies wasn’t wasted. First, you should know that these photos are a bit misleading. They do not represent how I would actually ship my box. My goal is to show off the cookies, but here are my best tips for actually packaging up the cookies and shipping out your boxes…

…start out by wrapping any cookies that are more fragile in plastic wrap or plastic food bags

…be sure to package the heaviest cookies on the bottom and the lightest cookies on top

…arrange a layer of shredded paper, bubble wrap, or tissue paper between each new layer of cookies.

…pack your cookies snug in your box to keep them from moving during shipping.

…for the final layer of your box, I like to use shredded paper, bubble wrap, or tissue paper. This will further help the cookies to stay snug and in their place.

…pack the box inside a large cardboard box with about two inches of space all around and fill in the empty space with bubble wrap, as this provides just another layer of protection for your cookies.

…seal the box well with tape and then write fragile all over it.

Step Six: Ship Your Box

I ship via UPS or Fed-Ex, I’ve found them to be pretty reliable. Ship your cookies via two-day air because it’s important to get your cookies to their recipient as soon as possible. My biggest tip? If possible, avoid the post office, in my experience, that does not end well.

side angled photo of 2019 Holiday Cookie Box

And that’s all I got! These are my best tips and tricks that I’ve learned throughout my past years of creating cookies boxes. Hoping this year’s box inspires you all to make your own. It’s truly the best gift you can give…who doesn’t love cookies?!

Question: what are all of you baking up this holiday season? What are your BEST tips in creating cookie boxes? I’d love to hear how you guys do it!

horizontal photo of 2019 Holiday Cookie Box

If you make your own 2019 holiday cookie box, be sure to leave a comment and/or give this recipe a rating! Above all, I love to hear from you guys and always do my best to respond to each and every comment. And of course, if you do make this recipe, don’t forget to tag me on Instagram! Looking through the photos of recipes you all have made is my favorite!

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Comments

  1. Really excited to start my cookie boxes! I will be making them for the first time this year! I have one question. You say that more fragile cookies should be separately wrapped in plastic wrap/baggies. I am wondering from your recipes above, which ones you decided to wrap and what you consider to be a “fragile cookie”.
    Thanks for sharing this!

    1. Hey Camila,
      I just made that as a suggestion, the box I made I was sure to share all cookies that are great for boxing. I hope you love the recipe, please let me know if you have any other questions. Happy Holidays! xTieghan

  2. Can I freeze either the dough or the already baked cookies ahead of time ? Which would be easier and how far advance would you suggest doing this ?

    1. Hey Serena,
      So sorry I am not sure for which cookies you are referring to? Please let me know how I can help! xTieghan

    1. Hey Emily,
      I would say about 1 week. I hope you love the recipe, please let me know if you have any other questions! xTieghan

    1. Hey,
      I used cardboard boxes and then ornament dividers inside of them. Please let me know if you have any other questions! xTieghan

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