Homemade Oreo Cookies

There’s a lot of great things about Boston – one of them being Flour Bakery.  Joanne Chang, the owner and brains behind the operation, decided that her degree in Applied Mathematics & Economics from Harvard and thriving consulting career wasn’t making her jump out of bed with excitement every morning, so she decided to pursue her love of cooking.  And after spending several years at several jobs as a pastry chef in Boston and NYC, Flour was born – and it’s now one of the best bakeries in Boston (in my opinion anyway!), with three locations throughout the city and it’s very own cookbook! Love inspirational stories of success such as that one!

My first Flour experience was a mixed box of treats – one of them resembling a whoopie pie, one of my all-time favorite desserts.  But when I bit into it, it wasn’t in fact a whoopie pie – it was actually an Oreo! Tasting very similar to everyone’s favorite cream filled cookie, but softer and MUCH bigger – bonus!

I’ve been meaning to try these for years now so Christmas was the perfect opportunity to give them a whirl.  They took a bit of time to make, primarily because of the chilling time required for the dough, but I’ve always been a firm believer that patience is a virtue 🙂

Homemade Oreo Cookies
*Adapted from Flour Bakery’s Recipe

INGREDIENTS
*yields about 16-18 large oreos

For the Cookie

1 cup (2 sticks) unsalted butter, melted

3/4 cup sugar

1 teaspoon vanilla extract

1 cup semisweet chocolate chips, melted

1 egg

1 & 1/2 cups flour

3/4 cup unsweetened cocoa powder

1/2 teaspoon baking soda

1 teaspoon salt

For the Filling
(this is actually doubled from the original recipe – I prefer Double Stuff if ya know what I mean)

1 cup (2 sticks) unsalted butter, at room temperature

2 teaspoons vanilla extract

3 & 1/3 cups confectioners’ sugar, sifted

2 tablespoons milk or cream

2 Pinches salt

1) In a medium bowl, whisk the butter and the sugar until combined. Whisk in the vanilla and melted chocolate. Add the egg and stir until well blended.

2) In another bowl, combine flour, cocoa powder, baking soda, and salt. Stir to blend them. Using a wooden spoon, stir the flour mixture into the chocolate mixture. The finished dough should feel like Play-Doh. Cover the dough with plastic, and chill for 1 hour.

3) Place the dough on a long sheet of wax or parchment paper. Use your hands to shape it into a rough log, about 10 inches long and 2 & 1/2 inches in diameter. Place the log at the wide edge of the paper and roll it around the log. With your hands on the paper, roll the dough into a tighter log, keeping the diameter the same.

4) Refrigerate the log for at least 2 hours  – after 2 hours it should be firm enough to slice without crumbling.

5) Set the oven at 325 degrees. Line 2 baking sheets with parchment paper or spray with non-stick cooking spray.

6) Remove the dough from the paper. Cut the log into 32 slices, each about 1/4″ – 1/2″ thick. Set them on the baking sheets 1 inch apart.

7) Bake the cookies for 20 to 25 minutes, checking them often after 15 minutes, or until they are firm when touched in the center. Let them cool completely on the sheets.

8) In the meantime, prepare the filling  – in the bowl of an electric mixer, beat the butter on low speed for half a minute. Add the vanilla and confectioners sugar and beat until smooth.

9) Beat in the milk and salt. The filling will be somewhat stiff and spackle’ish.

10) Place 2 tablespoons of filling on the flat side of 16 cookies. Press the remaining 16 cookies on the filling, flat sides against the cream, to evenly distribute the filling.  Be careful when pressing the top cookie down onto the filling.  I found that the stiff texture of the filling caused the top cookie to crack a little when I was pressing it down so just be gentle with it.

11) Store finished cookies in an airtight container for up to 5 days.

Safe to say you’ll never go back to store bought after having these puppies 🙂