Holiday Baking & Cookie Boxes

December is in full swing, and you know what that means? Holiday baking!

It’s been a while since I’ve done a more personal post. I hope everyone is able to safely celebrate the upcoming holidays, or at least take some time off to rest, do something you love doing, or indulge in some sweet treats (take a peek here if you want some ideas).

The December holiday season is the best, especially for baking. Chocolate, gingerbread, peppermint… Christmas flavors are some of my favorites! I’ve seen so many adorable baking creations on Instagram — from creative cakes, brownies, and chocolates. I’m more of a cookie fan, so you’ll always find me baking a batch of classic chocolate chip cookies every year. I mean, they’re the best! You can’t go wrong with a classic. And besides, I’m almost positive that Santa loves them too. 😉

However, to have some extra fun this year (and to have something to do on the weekend), I decided to go a little overboard this year and bake large batches of 3 different kinds of cookies and make boxes to gift to my family and friends. Trust me when I say this is a weekend endeavor. Thought I’d share my experience and some of the things I learned along the way!

I enjoy trying new flavors and playing around with recipes but I didn’t want to mess around with the boxes. I wanted to stick to classic recipes that wouldn’t fail, but are also creative and festive. Do you know who came to mind? HalfBakedHarvest. If by some crazy chance you are not familiar with HalfBakedHarvest, I seriously recommend you check out her blog and Instagram — it’s drool-worthy! She is incredibly talented at putting festive twists on classic recipes — especially in baked goods. I knew I had to try her recipes! Here’s what I ended up baking:

I’m no pro when it comes to baking, and I am a TOTAL amateur at decorating. If you take a look at the HalfBakedHarvest recipe links above, you’ll see how they are beautifully decorated. Nope, I am not on that level, so my cookies did not look like that (sorry to disappoint). I went with the basics: chocolate dips, drizzles, and sprinkles. Chocolate and sprinkles make everything better.

Here’s How I Made the Cookie Boxes

Anyway, I spent most of Saturday baking all 3 cookies in large batches and letting them cool overnight. The recipes weren’t difficult at all, but I did have 1 slip up. I HIGHLY recommend refrigerating the M&M dough for at least an hour (preferably longer) before baking it. The first batch I made I didn’t chill them long enough, and the cookies expanded and turned thin, super gooey. Trust me, they tasted AMAZING and there’s nothing wrong with some thin, super chewy, buttery cookies. I just wanted them to be a little thicker and chunkier so that they can be packaged easier and can withstand the transit. I chilled the next batch for about 2 hours and they turned out exactly how I wanted them to. 🙂

Other than that, everything else went smoothly. I was most worried about the sugar cookies since I never baked them before, but they were so easy to make! Like I said before, I’m not the biggest fan of sugar cookies. They seem kind of… bland? I’m a huge cinnamon gal, and it’s honestly more festive, so I figured I’d give this kind of sugar cookie a shot. It’s seriously so good — a little soft to bit into, but buttery enough to melt in your mouth. 10/10 recipe.

Last but not least, the chocolate espresso cookie. I originally wanted to add a hershey kiss to each “thumbprint” but decided against that because I was scared to mess it up. I decided to not make any indent and just decorate on top (it would be easier to pack up too). These were really quick to whip up — they required no chilling. The best part? It’s chewy, slightly gooey and cakey. They’re basically brownie cookies. What’s not to love?

Sunday was dedicated to packaging. I did a lot of research on how to best package cookies. I put in all the hard work and didn’t want them to go to waste. I had to pack them right. I got some treat boxes from Michaels, tissue paper, parchment paper, treat bags, and an assortment of candies (chocolate covered pretzels, kisses, marshmallows, chocolate caramels) and was ready to box.

Unfortunately, I got too carried away with the boxing (I was in the zone) and I forgot to take photos of the final product, so I’ll try my best to explain how I put it all together. I first lined the bottom with parchment paper, then some slightly crumpled tissue paper as a bottom cushion. I stacked several M&M cookies into cello bags (the ones that you can twist and tie on top) and put them in the box. For cookies that aren’t as stackable, such as the espresso ones, since they’re so round, I placed 2 of them flat side back to back and wrapped them in saran wrap. I then placed them into cupcake liners, which is a great way to create divides in the box. I added a couple of those. Lastly, I added the sugar cookies flat into parchment cookie bags and laid them flat in the box. In doing so, there will be some extra space, but not enough for more cookies.

Here’s a hack: fill up the rest of the space with candy.

The best ones? Marshmallows (I found some cute Christmas tree shaped ones), Hershey kisses, candy canes, and chocolate covered pretzel sticks. Marshmallows and kisses act as cushions that can be easily placed anywhere in the box that has some wiggle room, while candy canes and pretzel sticks add more volume and height if you need to fill up some extra space at the top, without adding a ton of weight that could break your cookies.

Basically, fill up the box so that when you close it, you can give it a little shake and nothing should move.

Another tip: make sure each and every cookie is wrapped to ensure freshness! And before closing your box, cover the contents with a layer of saran wrap to give it a final seal. I honestly felt so wasteful doing this, but this is to keep the cookies fresh in transit!! Now, back to the fun part: decorating the box. I already used decorative boxes, so I just added some extra ribbon or a bow on top for added fun.

Lastly, place each box inside a larger box and make sure it is padded with some kind of packaging filler. I happened to have some extra bubble wrap on hand from packages I’ve received to reuse, so I stuffed them in the empry space. Ta – da! They are ready to be mailed!

I hope you enjoyed! I seriously wish I took photos of the actual box so you can all see exactly how I packaged them, but I got carried away! I’m sure if you’re baking and mailing cookies, you’ll find your own creative ways to keep your cookies safe and fresh.

What are you all baking this season? Are you giving any baked goods away? Would love to hear your favorite recipes and tips on creating cookies boxes!