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It’s finally here! Our 2020 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 of our most favorite Christmas cookies and bars. There’s everything from caramel snickerdoodles, chewy gingery molasses 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 will love you just that much more. Trust me, there’s no better gift than a box full of homemade cookies, especially this year!

overhead photo of 2020 Holiday Cookie Box

Today is the day! I am finally sharing my 2020 Holiday Cookie Box with you guys. And while some of the cookies are tried and true favorites, there are also some new ones too! And you know? I’ve loved all my previous cookie boxes (see my boxes from 2017, 2018, and 2019). But this year’s box might just be my favorite. For the last three years I’ve done a square cookie, but this year I switched it up with a slightly larger rectangular box and I could not love this box more!

Why the switch up? Well, I’ve actually always wanted to do a large rectangular box but just never found the right one. This year I had the perfect box and figured if there was ever a year to make “my ultimate dream” cookie box, it’s this year. 2020 has been an interesting one, to say the least. So I feel like ending the year on an extra sweet note is the only way to do it up right!

And to that point, this year especially, a cookie box feels like the perfect gift. I know many of you are celebrating the holidays a little differently, hosting smaller crowds, and staying home instead of traveling. If you aren’t able to see friends and family this holiday season, shipping them a cookie box, or dropping a box off at their doorstep, is the sweetest way to let them know you’re thinking of them this season.

Trust me! This is one of my favorite Christmas traditions that I do every single year. I love setting aside a day just for baking cookies. The last couple of years I’ve gotten Asher involved as well. Together we bake away all day, it’s the best. We’ll usually spend one day in the kitchen baking, then another day packaging them up at night to be delivered or shipped the following day. It definitely takes some time and effort, but we really love putting these boxes together. It’s always so much fun!

With that, let’s jump right in and talk about all the steps you’ll need to take to create the perfect box. I’ve learned a few tips and tricks over the years!

overhead prep photo of all the cookies on a trey

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 of 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. For this year’s box, I expanded a bit and baked up eight different cookies. Again, I figured it’s 2020…anything goes…and when it comes to Christmas sweets, the more the merrier!

With that said, my box is large and you all will most likely be using smaller boxes, like the boxes we created with Etsy. If that is the case, just stick to four to six of your favorite cookies.

overhead prep photo of all the cookies on the counter

Here are the cookies used in my 2020 Holiday Cookie Box:

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

Salted Caramel Pretzel Snickerdoodles

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

Crinkly Caramel Stuffed Brownie Cookies...for your Tuesday night pre-holiday cookie baking. Homemade crinkly brownie cookies, made with sweet milk chocolate, a touch of coffee, stuffed with gooey chocolate-covered caramels, then baked to perfection. Each cookie is finished with flaky sea salt for a cookie that's salty, sweet, and dangerously delicious. Each bite is crisp and crinkly on the top, but soft and gooey in the center. There’s nothing not to love about these sweet crinkly caramel stuffed brownie cookies.

Crinkly Caramel Stuffed Brownie Cookies

The Santa Clause Cookies | halfbakedharvest.com

The Santa Clause Cookies

Easy Hot Chocolate Lace Cookies | halfbakedharvest.com

Hot Chocolate Lace Cookies

Chocolate Covered Brown Butter Millionaire’s Bars | halfbakedharvet.com

Chocolate Covered Brown Butter Millionaire’s Bars

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

Slice n’ Bake Salted Chocolate Butter Pecan Cookies

Milk Chocolate Peanut Butter Truffle Brownies | halfbakedharvest.com

Milk Chocolate Peanut Butter Truffle Brownies

Other Cookies That would be Great too!

Holly Jolly Santa Cookies

Creamy Lemon Bars (leave the raspberries off)

Vanilla Ginger Wreath Cookies

Chocolate Peanut Butter Crinkle Cookies

Chai Gingerbread Cookies

Step two: Get a sturdy box

The box you use to package your cookies is very important, especially if you are shipping cookies overnight. 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, which is what I did for this year’s box. Dividers keep each cookie separate from one other.

If you’re looking to order a box, I LOVE the cookie boxes we created with Etsy. They’re just the perfect size gifting and will fit four to six different cookies. These boxes are great for dropping off to neighbors and gifting to family and friends in town. If you plan to ship your box, I’d recommend putting the cookie box inside a sturdier box with bubble wrap or packing paper to secure the box and ensure none of your cookies get banged around during shipping.

2020 Holiday Cookie Box | halfbakedharvest.com

(above is our Etsy collab box all filled up!)

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

Or, if you want to just ship just one cookie, give this Scalloped Treasure Cookie Box a try. It would be perfect for a batch of Hot Chocolate Lace Cookies.

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). Be sure to use a piece that is large enough to wrap overtop of the cookies when the box is full. This keeps the cookies safe and fresh.

overhead close up photo of 2020 Holiday Cookie Box

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.

overhead close up photo of 2020 Holiday Cookie Box

Step four: when to bake your cookies

As I mentioned above, I like to bake and decorate the cookies in the morning. Then I let them chill and package them up later that afternoon or at night. This way they are all 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!

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…

  1. Start out by wrapping any cookies that are more fragile in plastic wrap or plastic food bags.
  2. Be sure to package the heaviest cookies on the bottom and the lightest cookies on top.
  3. Arrange a layer of shredded paper, bubble wrap, or tissue paper between each new layer of cookies.
  4. Pack your cookies snug in your box to keep them from moving during shipping.
  5. 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.
  6. 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.
  7. Seal the box well with packaging 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.

overhead photo of 2020 Holiday Cookie Box

And that’s all I have for you!! These are my best tips and tricks that I’ve learned throughout my past years of creating cookie boxes. Hoping this year’s 2020 Holiday Cookie 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!

overhead horizontal photo of 2020 Holiday Cookie Box

If you make your own 2020 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. Where did you get your christmas tree cookie cutter? The Christmas tree cookie
    cutter that has the white icing with the mimi M&M’s on them?
    thank you

    1. Hi Doreen,
      Sorry, I don’t have a link for that, I drew the stencil for the tree. Please let me know if you have any other questions! xTieghan

  2. How many of each cookie do you recommend putting in each box? Making some up for people this year and I’m just working out how many of each type to make 🙂

    1. Hi Naomi,
      It really depends on the size of your box and which cookies you choose to make. There’s really no right or wrong way to assemble your boxes. xTieghan

  3. the link to the cookie boxes on Etsy didn’t work. Do you have a different link or product to suggest? Thanks.

    1. Hey Stephany,
      Sorry those are from last year and sold out. You can just use an old box you have and purchase ornament dividers for a similar result. Please let me know if you have any other questions! xTieghan

        1. Hey Stephany,
          I’ve used boxes of all shapes and sizes, I like to use an 8 inch square box or a rectangular box. Whatever you have will work! xTieghan

    1. Hey Phyllis,
      I drew that one by hand:) I hope you love the recipe, please let me know if you have any other questions! xTieghan

  4. This looks SOOOOOOO beautiful!!! Every year I make Pecan Sandies and Pecan Squares, now I want to add a few of yours to the mix and create a lovely box.
    Next year, I would so appreciate seeing a video of how you prep your box for shipping. I appreciate the details you provide, but a visual would be incredibly helpful.

    Lastly, your box on Etsy is really beautiful.

  5. Do you ever freeze already baked cookies while you are in the process of baking the remaining batches fir your cookie boxes?

    1. Hey Pamela,
      I prefer to make all of my cookies in one day, but you can certainly do this. I hope you love the recipes! Happy Holidays! xTieghan

  6. I will be making most of these and mailing them to my son who lives in Silverthorne. Such a beautiful place to live Thanks so much for sharing your amazing recipes. We appreciate them so so much

  7. My first attempt at cookie boxes this year! Going to use a few of your recipes – I can’t wait! Making them for the firefighters that live next door to me! Happy holidays!! Xx

  8. I wish you would have pictured your cookies in a box that you would actually ship. The cookies are beautiful as pictured but doesn’t show the reality of how you would box to ship. I would
    Love to see that.

    1. Hey Nannette,
      Besides the cookies on the top, this is exactly how I would ship them:) If you read through all of the tips in the blog post, I share the best way to do this. I hope this helps! Happy Holidays! xTieghan

  9. I LOVE LOVE LOVE LOVE LOVE LOVE LOVE LOVE LOVE LOVE this years cookie box!!!! SO AMAZING!! I think my top 5 favorite cookies that you have listed for this year are:Hot Chocolate Lace Cookies, Milk Chocolate Peanut Butter Truffle Brownies, Crinkly Caramel Stuffed Brownie Cookies, The Santa Clause Cookies, and ,Salted Caramel Pretzel Snickerdoodles !!!

  10. Everything you do is just beyond magnificent, Tieghan, but this cookie assortment is jaw-dropping. Who wouldn’t love getting a box of these beauties!!?! If I may ask, what are the pretty white cut-out trees and snowflakes? I love the decorations on them!

  11. Hi there! I am wondering how long these cookies will last? If I make them a week before Christmas, will they still be good to gift? How long will the people I give them to have to eat them all before they go bad?

    1. Hey Natasha,
      It depends on the cookie, but if you are planning to make a week in advance I would freeze all of the cookies. You really want to give these while the cookies are fresh. I hope you love the recipes, please let me know if you have any other questions! Happy Holidays! xTieghan

  12. I look forward to this post every year! Love it! Where did you get this exact box? Is it the Etsy box? I tried a few pastry box sizes but nothing works with the look I want.

    Also does the Santa cookies freeze well with buttercream/icing? I plan to make and deliver my boxes this weekend but have a few that won’t be delivered until next week. Hoping I don’t have to make buttercream twice.

    1. Hey Jackie,
      I have the Etsy boxes linked, otherwise I order my boxes from Amazon and insert ornament dividers. Yes, you can freeze the Santa cookies. Have fun making your box! Happy Holidays! xTieghan

  13. Absolutely gorgeous box! Since I’m
    Not doing a Cookie Baking Day with my girlfriends this year, my kids and I will be baking and delivering boxes this weekend (except I got Gladware because I’m plain like that…). Including:
    Chai Spiced Maple Sugar Cut-Outs
    Cranberry Orange Shortbread
    Gingerbread cookies
    Espresso Chocolate Shortbread
    Peppermint Chip Cookies
    And Cinnamon Sugar Pecans
    Can’t wait to bake and deliver!

    1. Hey Alissa,
      OMG, these all sound so so good! I am sure your friends and family will love these boxes. Thanks for sharing! Happy Holidays! xTieghan

  14. I buy square, plastic accessories boxes from The Container store and line them with waxed tissue paper. I then mike to use either red & white string or beautiful ribbon with a handmade gift tag. One year I hot glued acorns and pinecones to my gift tags. Each year is a bit different but I always strive to make my boxes look like a special gift. To be fair, I don’t have to ship any as we hand deliver just as I did with my Dad when I was a child.

  15. You have written a truly wonderful tutorial! I love your idea of the cookie box and your recipes look amazing. Thank you for sharing these things with us. Merry Christmas!

  16. Wow!! I’ve been waiting for this and your 2020 box does not disappoint!! I love it! You’ve inspired me to do cookie boxes this year and I used a couple of your recipes!
    -millionaire shortbread bars (these are so amazing- my favorite new cookie)
    – lace cookies
    – vanilla Ginger cutout cookies (I didn’t have any red candy for decoration so I chopped up some crystallized ginger to put with my sugared rosemary and I LOVE these)

    I also made a few other types and I’m prepping to send ASAP! I love that you do this. Thx so much for the inspiration!

    1. Hey Heather,
      Thanks so much for following along! I hope you loved the recipes and thanks for giving them a try! Happy Holidays! xTieghan

  17. Right after Thanksgiving, I bake a batch of cookies 2-3 times a week before Christmas, Each batch is cooled and then frozen. Once I have enough varieties, I package them the week before Christmas. This year I plan to drive them to nearby family & friends to do a quick hello and leave a little cheer.

  18. Planning to spend the day on Monday making cookies with my husband and besties! This is my first year doing cookie boxes and I’m so excited! I will be handing mine out (no shipping for me). The boxes will include:
    The Santa Clause cookie
    Peanut butter blossoms
    Shortbread
    Chocolate crinkle (the best cookie)
    and your Apple blondie bars
    I’ll also be adding some spiced pecans to mix it up a little!
    Can’t wait to have a full baking day!!!

    1. Hey Jamie,
      Wow!! This all sounds so phenomenal! I hope you love all of the recipes, have fun making your box! Happy Holidays:) xTieghan

  19. I wish I had read this last week =( I shipped my cookies USPS last Tuesday. Two of them are nowhere to be found (one includes other presents!) and the others arrived yesterday. Some of the cookies were ok, some were stale. I’m so disappointed.

  20. I’m so excited! I have taken the day off work on Friday to make my cookies. On the list are your wreath cookies from last year and the ginger molasses cookies. Thanks for putting the list together!

    1. Hey Christina,
      How exciting! I hope you love the recipes, please let me know if you have any other questions. Happy Holidays! xTieghan

  21. Love these!!!! Can’t wait to make a box. Would any of these cookies specifically be ok to make ahead and chill the dough? Not sure I will have a whole day to devote to these, may have to break it up over a few days! Thanks!

    1. Hey Val,
      Sure you could that, you could also just freeze the cookies after you bake them! I hope you love the recipes, please let me know if you have any other questions. Happy Holidays! xTieghan

  22. BEAUTIFUL!!! I am thinking we all need a HBH Holidays Cookbook! Picture: boards, boxes, brunch!!! Your site is the best! Happy holidays!

  23. Hi! I’m late in the planning, but your beautiful post gives me so many ideas! My cookie box will include: peppernuts (my grandma’s recipe), springerle (my other Grandma’s recipe), cherry mash bars, frosted sugar cookies, ginger cookies, and I’m not sure what else…by the way, how do you stay so slim? Thanks for creating such a beautiful blog!

    1. Hey Amy,
      Yum!! These all sound so great! I hope you love making your cookie box! LOL everything in moderation:) Happy Holidays! xTieghan

  24. Those all look amazing! I am a little behind the mark this year but my cookie box will include:
    – Millionaire Squares
    – Shortbread Cookies
    – Chocolate Lace Cookies (your recipe)
    – Nana’s Brown Sugar Fudge (best fudge ever!)
    – Ginger Spice Cookies
    – Sugar Cookies (gluten free)
    and maybe
    – Brown Butter Chocolate Chip Cookies (my husband asked that I NEVER make them again…they’re that good haha)
    Merry Christmas All!

    1. Hey Sheila,
      Wow! This sounds like an incredible box of cookies, I am sure your recipients with just love them! Happy Holidays! xTieghan

  25. Beautiful!

    I’m just bagging up some rocky roads to give out with gift deliveries. One year I’m doing a full on proper box!

    You should do a book chapter on this, it’s such a happy thing to do for others 🙂 xx

  26. Ummmmm, I thought you were going to make this beautiful box for me! Do you need my address? 😉 As usual, everything looks amazing, I did make the milk chocolate peanut butter brownies but they will not be making their ways into any boxes!!!!

  27. I made a little version of a cookie box for friends and family this year! Everyone LOVED it! After seeing this years box, I will be stepping up my game next year. Such a great idea! Thank you for sharing!

  28. I always look forward to seeing your cookie box each year! We were extra excited to do ours since we haven’t seen many friends or family this year. A tip that we use: take advantage of the freezer. We’ll either freeze the dough and bake off when needed, or freeze the baked cookies. They still taste perfect and that allows us to spread our baking out over a few weeks! We also like to add a savory or salty element to our box.

    This year’s box:
    – Ginger molasses cookies
    – Fudge
    – Parmesan sourdough crackers
    – Peppermint bark
    – Lindor truffles sprinkled in the box for a little something extra

  29. Amazing ! Mine will have :
    – Easy hot chocolate lace cookies (your recipe),
    – lemon bars,
    – chocolate orange shortbreads,
    – ginger brownies (your crinkle top brownie recipe but with candied ginger added),
    – coconut ice (a kind of fudge),
    – cream chesse sugar cookies,
    – and lastly honey caramel popcorn.

    I always gift my boxes to my coworkers and they are a huge success every year ! You definitively inspired me with this tradition 🙂

    1. Hey Syrine,
      Wow!! These all sounds so phenomenal, I am sure your coworkers are just going to love them! Happy Holidays! xTieghan