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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!
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!
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.
Here are the cookies used in my 2020 Holiday Cookie Box:
Salted Caramel Pretzel Snickerdoodles
Milk Chocolate and Peanut Butter Blondies (oldie but goodie HBH recipe)
Crinkly Caramel Stuffed Brownie Cookies
Chocolate Covered Brown Butter Millionaire’s Bars
Slice n’ Bake Salted Chocolate Butter Pecan Cookies
Milk Chocolate Peanut Butter Truffle Brownies
Creamy Lemon Bars (leave the raspberries off)
Chocolate Peanut Butter Crinkle Cookies
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.
(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.
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.
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!
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…
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.
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!
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!
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 !!!
Thank you so much Clare, I love your enthusiasm! Happy Holidays! xTieghan
Absolutely Gorgeous ?
Thanks so much Pamela!
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!
Hey there,
Here is the link for those cookies: https://www.halfbakedharvest.com/the-santa-clause-cookies/
I hope you love the recipes, please let me know if you have any other questions! Happy Holidays! xTieghan
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?
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
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.
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
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!
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
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.
Hey Marcie,
This is such great idea, thanks for sharing! Happy Holidays! xTieghan
Yummy! My boxes were small, but had peppermint meringues, mocha truffles, and salted caramel shortbread.
Hey Bethany,
These all sound so good, thanks for sharing with me! Happy Holidays! xTieghan
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!
Thank you so very much Linda! Happy Holidays!!
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!
Hey Heather,
Thanks so much for following along! I hope you loved the recipes and thanks for giving them a try! Happy Holidays! xTieghan
It would be nice to have pictures of how you packed your cookies for shipping to go along with your pointers.
Hey Rachel,
Thanks for your feedback! xTieghan
Reading this with a tissue in one hand….otherwise, gotta keep licking my lips..
Thanks so much Lavinia!
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.
Hey Penny,
This is such a great idea, thanks for sharing! Happy Holidays! xTieghan
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!!!
Hey Jamie,
Wow!! This all sounds so phenomenal! I hope you love all of the recipes, have fun making your box! Happy Holidays:) xTieghan
The cookie box every yr is my girls FAVORITE!!! Thank you!
Thanks so much Amy!!