I wanted to make a cookie box for a friend this year- a friend who, for some reason, seems to always have exactly what I forgot to buy, right before a big trip. For those of you in the big city- this isn’t a big deal. You walk down the street to New Seasons, REI, and Nordstrom Rack, get what you need, and be on your way. For us small-town folk, even Amazon takes a week. So here I am, trying to figure out how to make a delicious box of cookies, that won’t put her two-year-old (or mine) through the roof on a sugar high. Here’s what I found. A four-day process, with assembly on day 5, but it worked well for our family.

 

Day 1: Pour a glass of wine and mix up the doughs while your children are sleeping, and husband is not home. This preserves the lifespan of the dough and the sanity of mother. Make all doughs.

I started with a batch of a base butter cookie dough, modified from a recipe I found online.

I separated the dough into 5 different balls of dough to make 5 types of cookies. And I’ll be honest, by the time I was done making the balls, they all went in the fridge overnight.

Ball 1: Butter Cookie Dough Base. I do recommend making each ball a different shape, so that you can send over a cute note explaining what each one is. This one is the easy warm up.

Ball 2: Ginger Cookies

Ball 3: Chocolate Butter Cookies

Ball 4: Sugar Cookies

Ball 5: Linzer Cookies

These ones are the most complicated, but by far my absolute favorite.

Let them cool before stacking- in fact, I stacked mine day 4 when I did the frosting for the other cookies.

 

Day 2: Bake all 5 balls of cookies.

 

At this point, Day 3.

While the cookies from Day 3 were sitting in the fridge, ready to be decorated, I whipped up a batch of yummy oatmeal cookies, a batch of peppermint marble cookies, and some homemade peanut butter cups.

 

Peanut Butter Cups (which you can really use any nut butter with)

Peppermint Marble Cookies

Chocolate Oatmeal Cookies

Day 4: Here is where the fun begins. Or where you start to regret how much time you committed to making cookie boxes- not really sure.

I whipped up some peppermint whipped cream frosting and made sandwiches out of the marble cookies; Filled the Linzer cookies with a delicious strawberry jam and sprinkled a bit of powdered sugar on top for looks; left the gingerbread and the one ball of regular butter cookies just as they were; Dipped the sugar cookies in a Stevia Pumpkin Spice frosting; and then let everything else cool.

 

Stevia Frosting

Whipped Peppermint Filling

Linzer Filling

Day 5. Please don’t ask how much wine this took to get through.

Assemble the boxes the day you plan on delivering them or store them in the fridge.

I used an old tissue box and cut the lid off, and then some tissue paper to separate the frosted ones just in case they melt. I did half batches of everything listed above, and it made 5 big cookie boxes. So I imagine you can easily get 12 out of this if you make everything with the full recipes. Make sure to tell each recipient at least 3 times to put them in the fridge- otherwise the mess would be unimaginably gooey and not in a good way.

Deliver with a note that outlines your shapes.

We had: Chocolate Elephants, Marbled Peppermint sandwiches with frosting between in the shape of a heart, plus some small, marbled stars, Round Sugar Cookies half-dipped in pumpkin dip, traditionally shaped Peanut Butter Cups, Oatmeal Cookies, House-Shaped Gingerbread Cookies, smaller hearts for the Butter Cookies, and we used a mason jar lid and a kombucha bottle lid to make the Linzer cookies.

Enjoy!