Chocolate Cherry Surprise Cookies

One of my fondest childhood memories was helping Nana and Papa prepare for their annual Hanukkah soiree.  If I close my eyes just tight enough, I can picture myself in their kitchen; donning an oversized apron and covered in flour as we prepared dozens of scrumptious cookies.  After an afternoon of hard work, nothing was more rewarding than sampling the fruits of our labor.  While all of our baked goods were delicious in their own right, the Chocolate Cherry Surprise Cookies were by far my favorite.  Imagine a pillowy soft chocolate cookie topped with a layer of rich frosting, certainly a decadent enough treat on its own. . .but take a bite and you find a gooey marshmallow center and a maraschino cherry hiding inside. Truly the best cookie I have ever, ever had (let alone baked).

Unfortunately, my Papa passed away when I was just nine years old — he actually passed away during their Hanukkah party. Since I had such vivid memories of baking these together, I asked my Nana several years later for the recipe. She dug through all of her cookbooks and index cards, but came up empty handed. I scoured the internet as well, but nothing seemed to come close; it seemed as though these cookies would be but a distant memory.

If you read the introduction to this blog, you know that my Nana passed away in 2009 and that my mom and I were tasked with packing up all of her belongings. It was an emotionally taxing day, but on the kitchen counter in plain sight was a Pillsbury cookbook with a post it note marking a page. Lo and behold, there the recipe was with Nana’s handwriting calling out that it was my favorite cookie.

 Since then I have baked these cookies every holiday season, and I can feel both Nana and Papa in the kitchen alongside of me.

Cookie Ingredients

  • 3/4 cup sugar
  • 1/4 cup brown sugar
  • 1/2 cup of softened butter
  • 1/2 teaspoon of almond extract
  • 1 egg
  • 1 3/4 cups of all purpose flour
  • 1/2 cup unsweetened cocoa powder
  • 1/4 teaspoon salt
  • 1/2 cup of milk
  • 18 maraschino cherries, cut in half
  • 18 marshmallows, cut in half
  • *The original recipe called for chopped walnuts or pecans, but we always omitted them.
  • To make the cookies, preheat the oven to 375 degrees Fahrenheit.

    In a bowl, mix together the first 5 ingredients.

    In a separate bowl, mix the flour, cocoa, and salt. Gradually add the flour mixture to the sugar mixture, alternating between the milk and the flour.

    Drop cookies on ungreased baking sheet (though I line mine with foil) by rounded tablespoon.

    Press cherry half, cut side down, in each cookie. Bake for 6-8 minutes. Remove from oven and top with marshmallow half. Return to oven for 2 minutes more. Allow cookies to cool completely.

    Frosting Ingredients

    • 3 cups of powdered sugar
    • 3 tablespoons of melted butter
    • 1/2 teaspoon of vanilla extract
    • 3 ounces of semisweet chocolate, melted
    • 5 tablespoons of water
  • Mix frosting ingredients and spread over the marshmallows.
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