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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