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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 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.
Love! I really want to make cookie boxes for people, what a beautiful and yummy gift.
Thanks so much Mariah!
Ahhhhhh I’ve been waiting all year!!!!!
Thanks for following along Sarah!!
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!
Hey Christina,
How exciting! I hope you love the recipes, please let me know if you have any other questions. Happy Holidays! xTieghan
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!
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
BEAUTIFUL!!! I am thinking we all need a HBH Holidays Cookbook! Picture: boards, boxes, brunch!!! Your site is the best! Happy holidays!
Hey Natalie,
Thanks so much for your kind message and following along! Happy Holidays! xTieghan
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!
Hey Amy,
Yum!! These all sound so great! I hope you love making your cookie box! LOL everything in moderation:) Happy Holidays! xTieghan
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!
Hey Sheila,
Wow! This sounds like an incredible box of cookies, I am sure your recipients with just love them! Happy Holidays! xTieghan
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
Hey Kelly,
The rocky roads sound awesome!! Thanks for sharing:) xTieghan
OMG!! Your recipes are incredible and your styling and photos are STUNNING! Drooling!!!!
Hey Christine,
Wow, thank you so very much:) Happy Holidays! xTieghan
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!!!!
Hey Sarah,
LOL thanks so much for following along:) Happy Holidays! xTieghan
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!
Hey Bekah,
That is so awesome! I hope you enjoy making your box. Happy Holidays! xTieghan
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
Hey Hilary,
Yum!! These sound like such great choices for your cookie box. Thanks for sharing!! xTieghan
So so pretty!!! I always love seeing your cookie box every year!
Thanks so much, Becca!!
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 🙂
Hey Syrine,
Wow!! These all sounds so phenomenal, I am sure your coworkers are just going to love them! Happy Holidays! xTieghan