This post may contain affiliate links, please see our privacy policy for details.

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!

You May Also Like

Add a Comment

This site uses Akismet to reduce spam. Learn how your comment data is processed.

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

  3. Hi Tieghan!

    I am starting to plan my first holiday cookie box. What dimensions do you usually use? Also I know you usually use sturdy cardboard boxes but have you had experience with using metal tins and if so is one better than the other?
    And last question, I would love to do something chocolate dipped like you have here but have you ever had melt in the mail problems?
    Thanks so much!
    Maddie

  4. I love your cookie boxes!! They are a beautiful inspiration. I started selling mine because friends and family kept asking me if they were for sale. I used to send out to just a few friends each year but it looks like everybody wanted a taste 🙂 Check out my shop at http://sodessert.etsy.com/ and let me know what you think!

    1. Thank you so much Sonia! That is so awesome that you could make a business out of it! And the cookies look delicious! xTieghan

  5. Hi! I’m planning on doing a HBH inspired cookie box for our family gift exchange this year. We don’t do traditional gifts, and instead everyone brings a basket and enough of whatever they’ve made to fill everyone else’s basket. Since we’re up to 14 baskets (one per household) this year, it’s way easier than trying to get gifts for everyone! I’m planning on doing my baking and packaging on Wednesday, since Thursday and Friday will be spent helping get set up for Family Christmas. Since I’m not actually shipping them, do you have any suggestions on how to keep everything super fresh from Wednesday until Saturday when we do the basket exchange?

    1. HI! I would recommend keeping each cookie in separate sealed containers until you are ready to put the box together. I think that should keep them pretty fresh. Please let me know if you have any other questions. I hope you love all the cookies!! Sounds fun what you guys do! Thank you and happy holidays! xTieghan

  6. I love your ideas!!! Just a quick note— you do know that in rural areas, the UPS trucks dump off their packages at a central post office… and the US postal rural carriers take them onto the bad back roads…Amazon also dumps off package
    S at rural post offices. So, please don’t malign the US postal service’s delivery! How do I know all this? My husband is a Rural Carrier in Ohio. And the UPS drivers really do ‘ dump and drive off’ the packages. So, if you had crumbled cookies, it may not be the PO’s fault?

    1. Hi Cynthia! I did not know this, but in my neighborhood, that is not the case! USPS does not deliver to the house, only UPS… and it is super hard to deal with USPS in our area! That is why I do not suggest it, from personal experience! I hope you understand! xTieghan

  7. I love your holiday cookie box posts, they’re always beautiful! I’d like to make some this year myself, but I’m not sure how many of each cookie type per person?

  8. This looks absolutely stunning! Thank you for all the very helpful info too Congratulations on the huge success of your new book – I am about to order one for my daughter ?. A very Happy Christmas to you and your family!

  9. Those cookie boxes always look so amazing! I wouldn’t know who to send them to, but I might make some as hostess gifts this year. They just look so terribly cosy!

  10. I made the slice and bake chocolate drizzled butter pecan cookies today for the first time for my first cookie box. Omg, SO good! Thanks for inspiring me!

  11. I think that is the loveliest box of cookies I have ever seen! They all look delicious too!
    I totally love your blog; it is one I am sure to read every post. Thanks for sharing these recipes and tips for mailing.
    Happy Holidays to you and yours!

  12. Your box is gorgeous! I sent my cookie boxes last week and this year I included: ginger molasses cookies, chocolate covered caramels, peppermint bark, and a salty snack mix. I usually bake everything, but with a toddler I baked the cookies and then did store bought for the other treats. I usually like to throw in a savory food (this year was Trader Joe’s Step up to the Snack Bar mix) and typically do homemade chex mix. Since I used peppermint, I couldn’t mix everything together, so I packed everything up in (biodegradable!) wax paper bags, taped with fun washi tape, and packed in a cute Christmas tin.
    If people are short on time, I recommend freezing cookie dough balls or baked cookies. That way, you may just need to pull out everything and bake! I froze my baked cookies a few weeks ago and they still tasted perfect when I took them out!

  13. I LOVE this post! I have organized a cookie exchange at my school (I am a teacher) for the past few years and people love it as a way to try new ideas! It is next week, so I am still deciding what to make, so this gives me lots of inspiration. My mom hosted or attended these exchanges every year when I was growing up, so I love the tradition of cookies. And I love to share with neighbors who do not bake (most of them!) at our annual luminary night.
    Thank you for all of your inspiration!

  14. This box is beautiful. I love baking and gifting holiday cookies…the perfect excuse to go sprinkle crazy. I usually package cookies in fancy cellophane bags and place those bags in festive handled paper bags with tissue. I have found a great place to purchase all of my packaging needs. The site has a large variety of cellophane bags in different sizes and designs. The only downside is you have to purchase boxes of 100 bags. That is not a problem for me as I bake lots of cookies all throughout the year to gift to friends and I also share bags with other baker friends. The site is PaperMart.com. In addition, the ribbon selection is amazing and the prices are very reasonable.

  15. December 8th

    Hello,
    Where did you purchase most of your Christmas or Hanuka cookie cutters?
    Thank you.

    Rita

  16. So gorgeous!

    I’m in Scotland, and cookie boxes are not usual here. What I do do though is make Bags of cookies (cellophane and ribbon ties) or cute decorated Christmas decorated cupcakes in boxes of 4 or 6, to give when delivering presents.

    I also love the no bake of Nigella’s Christmas Rocky Road (on her website) decorated with a bit of edible glitter or sprinkles they are super cute. Or shortbread love that too.

    Looking forward to seeing your new cookies this week. ? xx

  17. Big HBH fan here! I have made many of your recipes now and love them all. You have such a good combination of quality, healthy ingredients, easy to follow directions, and delicious results.

    I think nothing is as special and personal as a homemade gift. And cookies? Doesn’t get any better than that! Growing up my mom had us bring cookie boxes to our neighbors. Now my daughter and I bring them to our neighbors and leave one for our postal worker and UPS drivers. I look forward to incorporating your recipes into our tradition! Thank you for sharing!

  18. Good morning Tieghan! Loved this post! Your cookies are all so pretty. I really need to start my XMAS baking here shortly. I don’t ship any though. And I always make too many, freeze them, and most times, we are still eating them in the spring! One thing I always have to make for everyone are confetti squares. Then I just pick a few other things (cookies or squares). Normally, I only make a couple of “the usuals”, and then try a few different ones. Another thing I do sometimes, is half the recipes so I can get way more variety and not take up so much space in the freezer with full batches. , You have given me a nice selection to choose from. I also had to tell you that I ordered (and received) your new cookbook last week! Can’t wait to dig into it!