Chocolate Chip Cookie Sandwiches

Chocolate Chip Cookie Sandwiches

Filled with OREO® and Milano® Butter Cream

Dipped in Semisweet Chocolate

Or, as I like to call it,

 The Sweet Dream™


It is holiday time and we are stressing out trying to find time to make all the varieties of cookies that we normally don’t even think about the rest of the year.  I know, I know - these once a year cookies are part of our family holiday tradition, but are we just wasting our holiday dessert binge calories?

The Chocolate Goddess thinks it’s time to come up with a new cookie that we could love every day of the year. I am constantly thinking of new and delicious flavor combinations, permutations, and variations of ingredients for desserts.  But coming up with a new cookie is one of the biggest challenges; people are tough cookie customers.  The general public’s palettes need to be wowed in order to fall in love and stay in love with a cookie.  It should be obvious since it has been a while since we have been spellbound by the cookie industry.   

The 1900’s were an impressive time for a trilogy of captivating new cookie inventions that are still the favorites today.  First and foremost, the Oreo cookie that was invented in 1912 by Nabisco.  It was a transformed version of the, less sweet, Hydrox cookie that originated in 1908 and was manufactured by Sunshine Biscuits.  The popularity of the oreo really has staying power!

The next long standing preference of the cookie world was given to us through the baking genius of Ruth Graves Wakefield, owner of the Toll House Inn located in Whitman, Massachusetts.  Ruth and her assistant Sue Brides came up with a variation on a cookie they had been serving to guests at the Inn by adding chocolate bits. It became known as the Toll House Cookie and later, our familiar Chocolate Chip.  A staple in my household, there must be Chocolate Chips available 365 days a year.  I keep them stocked in my freezer and defrost them regularly.

 The third object of desire came to us by the talented baker Margaret Rudkin, who started The Pepperidge Farm Bakery.  She duplicated a cookie she had in Italy, which was a single layer biscuit topped with dark chocolate and called it the Naples.  Margaret became aware the cookies were sticking together when packaged and shipped, so she redeveloped the concept and sandwiched the chocolate between two cookies and premiered the delectable, Dark Chocolate Milano.

There are other biscotto of the industry that people enjoy, of course, but these three cookies have been the clear darlings and have been venerated with the undying love and devotion of a captive audience, some for over a century.

The OREO, Chocolate Chip and Dark Chocolate Milano remain the stars of the cookie world.  But what if I combined all their spectacular flavors in one cookie, would there be a magnificent melding of flavors? Well, I did and there was.

The flavors unlocked my childhood dreamland of flavor favorites.

Besides being scrumptious, these cookies are visually delicious.

Here is hoping they have staying power all year long!


Happy Baking!

And Remember

Always Stay in Touch with Your Inner Goddess!


Remember to always gently fold in chips.


A two tablespoon scoop facilitates making the cookies all the same size making it easier to pair up the sandwiches.


Perfect, don’t over bake chocolate chips.  Remove them from the oven just as the edges are a little golden and the interior just loses its wet sheen.


Gently roll or tap cookies.  I like some bigger chunks of cookies in the frosting.


Go ahead, eat one while you’re preparing the frosting.


Fold crumbs in by hand so they do not become pulverized.


A 2 tablespoon scoop of frosting is perfect.  Just press it down a bit.


Use good chocolate.  I like the Ghirardelli baking bars.

Tilt cookie and dip it in the chocolate.

Ingredients for The Sweet Dream™

Chocolate Chip Cookies (Recipe may be doubled)

2 ¼ cups all-purpose flour

1 teaspoon baking soda

1 teaspoon salt

8 ounces (2 sticks) unsalted butter

¾ cup granulated sugar

¾ cup light brown sugar

1 teaspoon pure vanilla extract

2 lightly whisked large eggs

1 cup finely ground walnuts

2 ½ cups semisweet chocolate chips

Makes approximately 30 cookies, 15 sandwiches

 Milano and Oreo Cookies n Cream Buttercream

1 pound (4 sticks) Butter

2 teaspoons Pure Vanilla Extract

2 pounds (2 boxes) Powdered Sugar

Heavy Cream for thinning, 1 tablespoon at a time

1 cup Chopped Oreo Cookies

1 cup Chopped Dark Chocolate Milano Cookies (10 cookies)

Chocolate Glaze for Dipping

16 ounces Ghirardelli Semisweet Chocolate

2 teaspoons Canola Oil

Baking Instructions

Preheat oven to 375 degrees. 

Line cookie trays with parchment paper.

Combine dry ingredients.  Set aside.

Cream butter and add sugars. Beat until creamy.

Add whisked eggs and combine.

Slowly add dry ingredients. 

Add walnuts.

           Gently incorporate chocolate chips

Drop by scoopful (I use a size 40 scoop, that holds 2 tablespoons of liquid).

Bake for 9 ½ minutes to edges are just golden brown.

Let cool on cookie sheets completely before removing.

Instructions for OREO and Milano Buttercream

Bring butter to room temperature.

Beat until creamy.

Add vanilla and incorporate.

Slowly add powdered sugar starting on low to avoid dusting yourself with powdered sugar. Then beat until perfectly creamy.

Place Milano’s in a bag and gently crush leaving some larger pieces.  Set aside.

Place OREOS in a bag and gently crush leaving some larger pieces. 

Fold into buttercream by hand.  It is worth the effort in order to have some larger bits in the filling.

Instructions for Dipping

I like real chocolate.  That is why I used Ghirardelli semi sweet bars.

Break chocolate into pieces in heat proof bowl.  Reserve a few small pieces to temper chocolate.

Melt on low, 30 percent power and stir after every 30 seconds.  Don’t become inpatient and crank it up, the chocolate will burn.

Just as chocolate is almost all melted, remove from microwave and stir in remaining bits.  Stir vigorously until all melted.  Stir in the canola oil completely to make it pliable.  Don’t use more or the chocolate won’t dry. 

Tilt sandwiches and dip.  I coated the bottom too.  Let dry on waxed paper for easy removal.  Place on rack when they look dry and let them sit overnight.