Frankly, the inspiration for my first Christmas Cookie box started when I took Markus to Barnes & Noble on a snow day. He browsed the kid’s section for a new crime novel. I hit up the cookbook section, per usual. I picked up Cookies by Vaughn Vreeland because I’m a sucker for any recipe book tied to the NYTimes. The recipes looked delicious and I immediately thought…I should make these…like…all of these!
Keep scrolling and you’ll see what went into my first every Christmas cookie box, including links to every recipe. I’ve also got some tips for all you first-timers to make the entire process feel more manageable! If you want to make a cookie box for a holiday or special event, this is your guide!
What’s in My First Christmas Cookie Box – Quick Look
I baked over 400 cookies for my first cookie box. Honestly, I should have made more! As soon as friends and family caught wind that I was baking up a storm, the text messages started flying in. Moral of the story, people LOVE holiday cookies.
Since this was my first ever Christmas cookie box I went with a few guiding principles to keep things manageable. My goal was variety. I wanted a mix of flavors, textures, and bake styles so the box felt special, balanced, and doable for a first-timer.
Here’s how I approached it:
- A few elevated classics (because people love a familiar cookie done really well)
- Some bold, holiday-forward flavors like ginger, spice, and citrus
- Different textures: chewy, crisp, fudgy, buttery
- At least one bar cookie to break up the scooping and shaping
- A couple of make-ahead-friendly options that freeze well
- And a few non-cookie treats to add variety and bulk without extra baking stress
Here is the complete list of what I put in my first Christmas cookie box. I also included honest notes on what worked well, what I would change next time, and tips I wish I had known before.
The Cookie Recipes in My First Christmas Cookie Box
- Salted Butterscotch Chocolate Chip Cookies from Cookies by Vaughn Vreeland: This recipe made my Christmas cookie heart skip a beat! It’s a good idea to include an elevated classic in your cookie box. The browned butter and toffee chips make this a holiday worthy cookie.
- Chewy Ginger Molasses: A Christmas cookie box without something gingerbread-y is a straight up crime. These cookies are incredibly chewy and I’ve gotten rave reviews already! NOTE: When making these, form them into balls and then refrigerate again before baking. Once chilled, go straight from the fridge to the oven. This will ensure you get a really nice cracked, crinkled top.
- Classic Sugar Cookies with Icing: There are a million recipes for cut-out sugar cookies. This recipe is super easy to follow! The cookie bake up perfectly and keep their shape. My only tip is for the icing. I’d recommend adding a bit more powdered sugar to the icing to make it thicker. The thicker icing is nice for piping a border onto the cookies. Once you’ve got the borders piped, you can thin out the icing and use it to flood the inside of the piped border. I find that using a thin icing from the beginning just results in a mess that runs off the side of the cookie. NOTE: This dough freezes SO well. Go ahead and make the dough weeks in advance to get a head start on baking season.
- Sweet Almond Swirled Christmas Cookies: These cookies have a sweet almond flavor and crunchy texture. They are absolutely delicious but the recipe doesn’t quite advertise the prominence of the almond flavor. NOTE: Do NOT overbake these or else you’ll have a pile of crackers on your hands.
- Lemon Crinkle Cookies: With all the warm, deep flavors of winter it’s nice to include something bright and citrusy. These Lemon Crinkle cookies do the trick and I wouldn’t change a thing about the recipe! They’re perfect.
- Chocolate Brownie Cookies from Cookies by Vaughn Vreeland:. 10/10. Wouldn’t change a thing. The ONLY thing to keep in mind: this recipe doesn’t multiply well. Once you’ve made the batter, you basically need to scoop them immediately and get them in the oven. This ensures a perfectly glossy finish with beautiful cracks and crinkles. If you have more than one oven and lots of baking sheets, you can double the recipe without any problem. Otherwise, you’ll need to make these one batch at a time to avoid having excess batter sitting around waiting to be baked.
- Maple Apple Blondies from Sweet Tooth by Sarah Fennel: THIS. IS. UNREAL. Make it now and forever, Amen. The most delicious blondie that your autumn loving heart could every want for. The best part? I subbed in Bob’s Red Mill Gluten Free Flour and they were STILL incredible. I give this recipe a 100 out of 10. How’s that for a resounding review.
- Raspberry Thumbprints: These are a classic but I’m not sure I’ll make them again next year as written. The icing drizzle makes them SUPER sweet. My husband LOVES them but I’m not a huge fan of a sugar overload. That said, these are another great cookie to make well in advance. The dough freezes really well, just make sure to shape the dough with the thumbprint before freezing. Also, make sure to go straight from chilled to the oven to help them keep their shape and avoid over spreading.
- Millionaire Shortbread Cookies by Vaughn Vreeland: These are decadent and amazing! The only downside: you have to make your own caramel layer using sweetened condensed milk. This means you’ll be whisking a pot continuously for about 20 minutes. The flavor is totally worth it but you’ll get a decent shoulder workout in the process. NOTE: Make sure you use the recommended pan size. This will ensure that each layer of the shortbread is the right thickness. I deviated and ended up with a top chocolate layer that is a bit too thick for my liking. Also, when the shortbread layer is done baking, use a flat spatula to gently press down the edges. This will help make the shortbread even in thickness. This way, the layers of caramel and chocolate will also be flat and even.
- Homemade Granola from Queen Ina Garten: Sooo, apparently not everyone is a cookie lover…crazy, I know. I’m a big fan of adding some non-cookie elements to your box. This is a great way to add bulk without too much additional effort. Ina’s granola recipe is the only recipe I’ll ever use! NOTE: Instead of cutting into bars, I break it into large chunks that are perfect for snacking or topping yogurt.
- Christmas Candy Salad: Okay, okay. This is totally not even close to a cookie but it’s a great add in! People LOVE a fun mix of candies! This is another good way to bulk up your candy box without more baking time.
How I packaged my first Christmas Cookie Box
Gift packaging is kind of my superpower! I love making a gift look as good as it tastes. When I packed my first Christmas cookie box, I had one big rule: the box had to be useful and keep the cookies fresh!
A lot of people go with paper bakery boxes, and those are perfect if you’re delivering cookies the same day. In my case, I was making deliveries over several days, so I needed the cookies to stay just as tasty when they arrived as when they came out of the oven.
Here’s what worked best for me:
Seal for freshness: make sure your container is airtight. For extra security, you can wrap each cookie into a cello bag and seal with a heat sealer.
Be Allergy Conscious! Nut and gluten allergies are common. It’s always smart to ask about allergies. If you’re not sure, wrap any items with allergens in separate packaging.
Use a classic cookie tin or a food storage container: choose something that isn’t overly holiday-themed so your recipient can reuse it all year.
Layer with parchment, wax paper or paper shred: this keeps cookies from sticking together and adds a neat, finished look.
Separate delicate cookies : use small paper liners, mini cupcake cups, or extra parchment layers for cookies that might crumble or have icing.
Stack wisely: heavier, sturdier cookies go on the bottom; lighter or decorated cookies on top.
How many to include? Aim for 3–4 of each variety, or 2 if the cookie or brownie is particularly large. This keeps the box balanced and lets recipients sample everything.
Include a Menu! This is an amazing way to elevate your cookie box and encourage your friends to taste each treat. Rather than guessing, they can get curious about each offering.
Storage, Freezing & Make-Ahead Tips I Wish I Knew Sooner
If there’s one thing I learned while making my first Christmas cookie box, it’s this: planning ahead saves your sanity. If I’m honest, I could have done a better job of this! Baking hundreds of cookies and coordinating deliveries is no small task. Also, knowing how to store and freeze them is a game-changer.
Here’s what I learned:
- Freeze dough in advance. Many cookie dough freezes beautifully, especially sugar cookies, thumbprints, and brownie cookie batter. Shape or portion it first, then freeze in an airtight container. When ready, bake straight from the freezer or thaw in the fridge. Make sure to check the baking times since this can change if you bake straight from the freezer.
- Keep baked cookies fresh. Store cookies in airtight containers at room temperature for up to a week. For longer storage, wrap them individually in plastic wrap before placing them in a tin.
- Freeze fully baked cookies . Many cookies, like chewy ginger molasses or chocolate brownie cookies, freeze well once baked. Layer with parchment, seal tightly, and pop in the freezer. Defrost overnight in the fridge or on the counter before gifting. This means you can make some cookies weeks in advance and then thaw them for gifting.
- Label everything . Especially if you’re making multiple batches. Write the cookie type and bake date on the container. This is especially important for any gluten free varieties you’re making! You definitely need to know which batch is gluten free and which is not. Do not trust your memory!
- Make ahead for less stress . Big batches like the almond swirls or chocolate chip cookies can be baked a week or two early and stored in the freezer. Then it’s just a matter of assembling your box when it’s time to gift.
What I’ll do differently next time
Even with all the planning, my first Christmas cookie box taught me a few things I’d tweak for next year. Here’s what I’d do differently:
- Bake even more cookies! Sounds crazy, but it’s true. 400 felt like a lot…until everyone started texting me begging for more. Next year, I’ll scale up so no one misses out.
- Prep more dough in advance. Freezing portions of dough ahead of time will save me from last-minute chaos and give me more flexibility with timing. I’ll probably start prepping in early November.
- Organize by delivery date. Label boxes by who’s getting them first. It makes transport and storage so much simpler.
- Include a few extra non-cookie treats. Candy salad and granola were hits. I might add a few more small, no-bake goodies to round out the box next year.
- Experiment with packaging. While tins worked perfectly, I want to try layering with mini compartments or dividers to make delicate cookies even safer and the unboxing a bit more “wow.” I’m also going to stay on the lookout for cute packaging throughout the year. Since I want something “non-holiday”, I’m thinking I may stumble on something at anytime!
All in all, the first cookie box was a huge success, and these tweaks will just make next year even sweeter…literally.
