2021 Holiday Cookie Box.

Our 2021 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. Some new…and some of our old favorites. There’s everything from classics…like snickerdoodles and gingery brown sugar molasses cookies. To Christmas monster cookies and the cutest little tree light cookies, plus a handful more. We’re packing up only the very BEST cookies and sweets this holiday season. There’s no better gift than a box full of homemade cookies, they are always enjoyed!

After a lot of requests, this year’s 2021 Holiday Cookie Box is finally here! I can’t believe the amount of people who’ve messaged me regarding this year’s box. I’m a little late (what’s new, we seem to always be late on things over here). But it’s so nice to see the excitement around these boxes. I always have a lot fun putting these together. It’s by far my favorite “tradition” I get to share with you guys every December. But man they do take some time to create. I think I spent two full days baking and photographing this box, I really wanted it to be just right! You guys make it worth though, and as I said above, they really do make the best gifts!

I’ve loved all my previous holiday cookie boxes (see my boxes from 2017, 2018, 2019, and 2020), but I wanted to make this one even more special.

What’s exciting is that this year we are back to celebrating with family and friends. Which means that many of us are traveling this season. Thankfully, cookie boxes are the perfect gift to bring along, whether you have a long or short journey. Showing up empty handed to any gathering is never ideal, but showing up with a cookie box?

Well, there’s really not a better gift.

And of course, if you still aren’t able to see friends and family this holiday season, ship them a cookie box. Or drop a box off at their doorstep. It’s the sweetest way to let them know you’re thinking of them.

This year’s box is in keeping with my “easy cookies” theme of the month. At the end of November, I said that I wouldn’t be sharing any tricky or overly decorated cookies. Because when it comes to holiday baking – easy and fun is 100% the way to go!

So, this year I made all my favorite, easy, but oh so delicious cookies. I’ve learned a few tips and tricks over the years, so I’m sharing all the details below!

How to 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. Normally I’ll bake anywhere from four to eight different cookies and then divide them between boxes. This year I did eight different cookies and made a nice size box.

With that said, my box is large. Many of you will most likely be using smaller boxes. If that’s the case, just go with four to six of your favorite cookies.

All the cookies used in my 2021 Holiday Cookie Box:

Holly Jolly Santa Cookies

Brown Sugar Maple Ginger Cookies (i let the glaze dry, then add to the box, but you can leave the glaze off too)

Easy Vanilla Bean Christmas Lights Cookies (tip, add 2 teaspoons meringue powder to the icing to help it harden and be better for packaging)

Christmas Monster Cookies

Salted Caramel Pretzel Snickerdoodles

Milk Chocolate and Peanut Butter Blondies (oldie but goodie HBH recipe)

Hot Chocolate Lace Cookies

Samoas Pretzel Presents

Other cookies that would be great too!

Slice n’ Bake Salted Chocolate Butter Pecan Cookies

Vanilla Ginger Wreath Cookies

Chocolate Peanut Butter Crinkle Cookies

Chewy Brown Sugar Maple Cookies

Step one: get a sturdy box

The box you use to package your cookies is very important, especially if you’re 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 using 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 have a wooden box and are just gifting to someone close to home, that is great too!

If you’re looking to order a box, I found this cute Christmas box set which comes with cute paper, ribbon, and tags. There’s also this box with an ornament design. Or if you’re looking for a simpler design, these are nice too, but a little smaller.

Lastly, these cookie boxes with a gingerbread house design are adorable too. I recommend smaller treats for this box though!

Either of these boxes are the perfect size for 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. Be sure to use bubble wrap or packing paper to secure the box. This will ensure that none of your cookies get banged around during shipping.

Another alternative is to use cookie tins. I love these festive square tins or these more classic round tins.

Or, if you want to ship just one cookie, give this 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.

Step two: 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. Or use small holiday cookie tins or boxes, or food containers that will fit inside your box.

Step three: 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 four: 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. 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 five: 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.

question: What are all of you baking up this holiday season? What are your BEST tips in creating cookie boxes? Share all your tips in comments!

Lastly, if you make any of the cookies from our 2021 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!