Caramel Filled Chocolate Cookies

I know, you are thinking "Man, these sure are some plain and boring looking chocolate cookies." I thought so too. I mean, I've complained about this before but it's hard (for me) to photograph anything chocolate because it's just brown! But fear not, they may be plain Janes on the outside, but inside is a different story...


Oh yeah, that's right. Molten, stretchy caramel, baby. Still think it's plain?? And what kind of fussy method do we use to put caramel in the cookies?

Haha. Actually, these are super easy to put together; it's just a crinkle cookie wrapped around a Rolo (for those of you unfamiliar with them, they are chocolate covered caramel candies). The only fiddly bit is unwrapping all them darned Rolos and resisting the urge to eat too many of them. The good news is, you need 48, and your average bag of Rolos has about 55. Yes, I counted. But what did I make these for? Here's a clue:


Can you guess? I'll just say it was a nerd-tastic weekend involving all kinds of yummy food, Mountain Dew, and lots of laughing. And, of course, cookies.

Caramel Filled Cookies, adapted from Culinary in the Desert
1 1/2 cups all purpose flour
1 cup whole wheat flour (preferably white whole wheat)
3/4 cup unsweetened cocoa (my favorite is King Arthur's Double Dutch)
1 tsp baking soda
1/2 tsp salt
2 sticks butter, softened
1 cup white sugar
1 cup light brown sugar, packed
2 large eggs, room temperature
2 tsp vanilla
48 Rolos (or substitute peanut butter cups or plain caramels)

Sift together the flours, cocoa, baking soda, and salt in a small bow. Set aside.

Combine the butter and sugars, beat until smooth and creamy, about 2 minutes. Add the eggs one at a time, incorporating the first before adding the second. Stir in the vanilla. Add the flour mixture and stir just until incorporated (I recommend doing this by hand with a big wooden spoon; the dough is pretty soft so it shouldn't be too hard on your arms). Scrape dough into a plastic bag and chill for at least 2 hours.

When you are ready to bake, preheat the oven to 350 F. Divide the dough into quarters, and work with one section at a time. Divide a quarter into 12 equal pieces of dough and roll into balls. Make sure you have unwrapped all the foil from your Rolos! Seriously!! Poke a hole in the center of each dough ball and insert a Rolo; shape the dough around the candy so that it is completely covered, and then roll between your palms back into a ball. Dip the top of each cookie in additional granulated sugar, if desired, and place on a parchment lined baking sheet, sugared side up. Repeat with remaining dough. Bake until the tops are firm and cookies are set, approximately 12 minutes. If you feel like the cookies are a bit too puffy looking you can press them down a bit right after they come out of the oven, but don't push too hard! You don't want to squish the caramel out. Let sit on the pan for a few minutes, and then transfer to a rack to cool completely.

Makes 48 delicious cookies that will keep you powered up on your next quest. Serve with milk. Or coffee. Or tea. Or Mountain Dew...I won't judge.