Caramel-Filled Chocolate Sandwich Cookies

Dsc02297 Until I was about twelve years old, I lived in a fairly small town of about 2,500 people, where it was safe for me and my brother to walk pretty much anywhere by ourselves.   Our town had a Main Street straight out of central casting, complete with a barber shop, library, pizza parlor, and a Rexall Drugs.  Sometimes, after I received my allowance, I would walk up to Main Street armed with the 37 cents (35 cents plus 2 cents tax) that it would cost me to buy a candy bar from Rexall's vast selection. 

I remember how I used to study the candy aisle, contemplating my selection as if I was picking out a fine wine:  Should I go for the Charleston Chew because it is the largest in size, or should I select the Sugar Daddy because it lasts longer?  Maybe I'll pick the Starbursts or Rolos, because they have several pieces;  but then there's that bag of Big League Chew--no wait, I'm not allowed to chew gum. 

Inevitably, no matter how much time I spent poring over my options, most of the time I came home clutching a Twix bar.  To me, it provided all of the great qualities that a candy bar should possess:  a chocolaty exterior, a chewy caramel interior, and an element of crunch in the form of a vanilla cookie.  There were also two pieces underneath the gold wrapper, so I could eat one, and then I would usually freeze the other for later. 

These cookies remind me of a sophisticated Twix bar, but with a chocolate cookie providing the crunch instead.  The buttery caramel filling is what really channels my candy bar of choice--it tastes very similar to the real deal.  By using a bittersweet chocolate glaze, as opposed to the Twix milk chocolate, there is a little more depth in flavor, but it still pairs well with the caramel.  The cookies are even delicious frozen!  Here are my tips for this rich and decadent dessert:

  • The cookie dough can be prepared up to 2 days in advance and refrigerated, wrapped in Dsc02291 plastic wrap. 
  • The cookies can be baked 1 day in advance and stored at room temperature, tightly covered.  You can also bake the cookies and freeze them for up to 2 weeks; fill and glaze them just prior to serving.
  • The vanilla extract can be replaced by the seeds scraped from one vanilla bean pod or by 1 teaspoon vanilla bean paste.
  • If you prefer, the glaze can be prepared using milk chocolate, semi-sweet chocolate, or even a high quality white chocolate bar (white chocolate chips will not work well).
  • If you don't have round cutters in the designated sizes, try to find something in your kitchen, such as the top of a glass, that you can use as a substitute.

Caramel-Filled Chocolate Sandwich Cookies

Makes about 3 dozen


For cookie dough

12 tablespoons butter, softenedDsc02288

1 cup sugar

1 egg

1 ½ cups plus 2 tablespoons flour

½ cup unsweetened cocoa powder

Pinch salt

For caramel

2 ¼ cups sugar

1 ¾ cups heavy cream

⅓ cup honey

1 tablespoon light corn syrup

2 teaspoons vanilla extract

4 tablespoons butter, softened

For chocolate glaze

12 ounces bittersweet chocolate, chopped

3 tablespoons butter

Dsc02290 Make the cookie dough:  In the bowl of an electric mixer fitted with the paddle attachment, beat the butter and sugar at medium speed until fluffy.  Beat in the egg.  Sift the flour, cocoa powder, and salt into a medium bowl and add it to the butter mixture at low speed until the dough comes together, about 2 minutes.  Gather the dough, divide in half, and form into 2 flat disks.  Wrap the disks in plastic and chill until firm, about 30 minutes. 

Preheat the oven to 350F degrees.  Line 2 baking sheets with parchment paper.  On a lightly floured work surface, roll out a disk of dough to about ¼-inch thickness.  Using a floured round 1 ¾-inch cutter, stamp out as many rounds as possible, and transfer them to the baking sheets.  Gather the scraps, reroll, and stamp out as many cookies as possible.  Bake the cookies for about 18 minutes, until puffed and set.  Let cool on the baking sheets and then transfer to a rack.

Make the caramel:  Oil the bottom and sides of a 9-inch square cake pan and line the bottom with a sheet of waxed paper that reaches up 2-inches on 2 sides of the pan.  Oil or spray the waxed paper with nonstick spray.  In a medium saucepan, stir together the sugar, cream, honey, corn syrup, and vanilla and bring to a boil.  Set a candy thermometer in the saucepan and cook over medium-high heat, stirring occasionally, until the temperature reaches 250F degrees.  Remove from the heat and stir in the butter.  Pour the caramel into the prepared pan and let cool for about 45 minutes.Dsc02293

Lift the caramel out of the pan and transfer to a cutting board.  Using a 1 ¼-inch cookie cutter, stamp out caramel rounds and sandwich them between the cookies, pressing to flatten slightly.

Make the glaze:  Melt the chocolate with the butter in a saucepan over medium-low heat, stirring occasionally.  If the glaze appears to be too thick, add a few tablespoons whole milk or cream to thin it out.  Line a baking sheet with waxed paper.  Dip the cookies halfway in the glaze, allowing excess to drip off back into the pot.  Set the cookies on waxed paper and chill for 20 minutes, until just set.   

Similar Posts


  1. How enticing! I too, loved Twix bars growing up--and still do. This looks like one tasty cookie recipe!

  2. peanut butter, chocolate, caramel oh my! the world's three greatest ingredients crammed into a cookie. yumyum.

  3. What a gorgeous cookie! I'd love one right now. I love your site-so many gorgeous recipes and fun insights.

Leave a Reply

Your email address will not be published. Required fields are marked *