As great as they are, chocolate chip cookies and snickerdoodles sometimes feel tired. They’re reliable standards, but the cookie world can be so much more. Therefore, in 2019, Shiri and Jamie will embark on the Great Cookie Challenge – a shared exploit during which we try to make 50 new-to-us cookies. Grab a glass of milk and your spirit of cookie adventure.

If I had time to make every cookie in America’s Test Kitchen The Perfect Cookie (2017), I probably would. Although my coworkers would probably kill me. Or make me buy them new pants. I will, in all likelihood, be purchasing a copy of this book once my library loan runs out (and I’m trying very hard to keep that to a minimum).

Thus, it isn’t shocking that all three of these cookies are from the aforementioned, and all turned out wonderfully.

Pumpkin Whoopie Pies

So here’s the thing: I actually like pumpkin. Not just the fake, Thanksgiving season syrup stuff (and I’m a basic enough bitch to admit I like that too), but actual pumpkin. When we lived in Portland, as with the mushrooms I mentioned in 100 New Recipes Week #4, I loved going to the farmer’s market to check out the varietals and talking to the growers about the best ways to use each of them. Kabocha, technically a squash but sweeter than butternut or acorn, ended up being my favorite and can be used in almost everything from Thai curry to pie. But they’re tragically difficult to find on the East coast.

All that to say, I’ll grab any chance I can find to try recipes that utilize this much maligned, oft-abused gourd in ways that show off its true potential. By true potential, I mean in a manner in which you can actually taste it, something this lovely, little sandwich cookie does. Not too sweet, utilizing cinnamon, allspice, and cloves, which enhance the earthiness and richness of pumpkin rather than covering it, and adding the perfect accompaniment of cream cheese frosting. I ate several of these after they were done, which, as I’ve mentioned, isn’t something I usually do.

And you can skip the pastry bag; I used a 2 tablespoon cookie scoop to measure these out onto the pan, and it worked just fine.

Chocolate Sugar Cookies

Sugar cookies are usually a production. You make the dough. You put them in the fridge. You wait. You roll and cut or slice. You put them back in the fridge. You bake. You decorate. Even I get impatient, and the kids? Forget it.

So when I let Zora pick cookies for us to make and she flipped through the book and said, “Chocolate Sugar Cookies,” I almost said no.

Good news, cookies lovers: these are the easiest sugar cookies ever and they’re chocolate. I had never made chocolate sugar cookies before. I hadn’t even considered it. Why? No idea. But they go right from mixer bowl to pan to oven with no fridge time and they come out perfectly. Additionally: rolling things in sugar only makes them better. Natural law.

Confession: I left the butter out to soften and whipped it very well but didn’t melt it because I didn’t feel like washing another bowl. It didn’t seem to matter.

Chocolate Chunk Oatmeal Cookies with Pecans and Dried Cherries

Jamie and I have taken to asking many of the folks we speak to on The Great Big Beautiful Podcast if they have a favorite cookie in order to spark our own baking inspiration. When we spoke to author Ronald Smith, he cited a well-made oatmeal raisin as his top choice, so I searched The Perfect Cookie for a recipe. The only one I could find is gluten-free, to which I’m not opposed but for which I didn’t have the proper ingredients. Gluten-free baking requires the proper ingredients (I discovered this the one time I tried it and ended up with, after three hours in the oven, a pool of oil with apples and burned bits of flour substitute floating in it rather than an apple cake). What I did find, however, was the aforementioned.

I didn’t have pecans or dried cherries, but I did have almonds and a raisin mix that included dried cherries, which wouldn’t affect consistency or baking time and, quite frankly, I like my fruit cookies with some chocolate in them anyway.

The product tastes like granola and can be either dessert or breakfast.

Not that I’ve had them for breakfast.

I’ve totally had them for breakfast.

Not sure where this journey is going to take me next, but I’m sure it will be delicious.