Rolo Stuffed Chocolate Chip Cookies

Rolo Stuffed Chocolate Chip Cookies: The Briarwood Baker

It’s been exactly a week since leaving the University of Cambridge where two months of traveling, new experiences, fantastic professors, and wonderful friends made it the summer of a lifetime. As I wrote before, I was fortunate to have a kitchen available which subsequently turned into the place where we all congregated every evening to talk, cook, eat, play beer pong, etc. etc. Because my friends and I took full advantage of the fact that we could cook or bake, that’s what we did…whether it was a giant ostrich egg, Derby pie (side note: the recipe won the Kentucky State Fair’s Derby pie contest), scones, cookies, and A LOT more, food proved to be something that brought us together on a daily basis.

Rolo Stuffed Chocolate Chip Cookies: The Briarwood Baker

These cookies were one of those concoctions made in the tiny kitchen of Cambridge’s Bishop Bateman Court and they were fabulous. Even though they look like plain chocolate chip cookies, little do you know there is melt-y caramel and chocolate goodness hiding in the center of each cookie. After a day of classes and essay writing, plain chocolate chip cookies would not suffice, which resulted in my decision to stuff the centers of the cookies with Rolos and to brown the butter in the cookie batter to give it an extra nutty/caramel-y flavor. My friends and I bonded even more while making these cookies multiple times, which just goes to show that all you really need in life are good friends and good food.

Rolo Stuffed Chocolate Chip Cookies: The Briarwood Baker


Rolo Stuffed Chocolate Chip Cookies

12 tablespoons unsalted butter

2 cups plus 2 tablespoons all-purpose flour

1/2 teaspoon baking soda

1/2 teaspoon salt

1 cup light or dark brown sugar, packed

1/2 cup granulated sugar

1 large egg plus 1 egg yolk

2 teaspoons vanilla extract

1/2 cup chocolate chips

About 20 Rolos

Preheat oven to 325 F. Line a baking sheet with parchment.

Melt the butter in a small saucepan over medium heat, whisking constantly. After a couple of minutes, the butter will begin to foam; continue whisking until the butter is brown and gives off a nutty aroma. Make sure to continually whisk during this process to prevent burning. Immediately remove the butter from the heat and pour into a separate bowl to cool slightly before using.

Whisk flour, baking soda, and salt together in a bowl, set aside.

In a stand mixer with a paddle attachment, mix the butter and sugars together until blended. Beat in the egg, yolk, and vanilla. Add the dry ingredients and beat at low speed, just until combined. Stir in the chocolate chips.

Roll roughly 2 tablespoons of dough into a ball. Flatten the ball thinly into a disc in the palm of your hand. Place one Rolo in the center of the disc. Bring the sides of the disc up around the Rolo, making sure to completely encase the center with the dough. Roll into a ball. If desired, press a couple of chocolate chips on the outer surface of the ball (this is purely for aesthetic reasons, but hey, a little more chocolate never hurt anyone).

Bake 10 – 15 minutes in the preheated oven.

Makes: approximately 18 – 20 cookies


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