Caramel-Stuffed Chocolate Molasses Crinkle Cookies

Servings: 20 cookies serving(s)

Prep time: 80 minutes

Total time: 2 hours

Cooking time: 25 minutes

Take me to the recipe

Caramel stuffed molasses crinkle cookies are festive and delicious. For variety on your cookie plate try topping some with caramels too.  

Caramel-Stuffed Chocolate Molasses Crinkle Cookies

These crinkle cookies were intended to be special Valentine’s Day cookies for my kids, only they didn’t last until Valentine’s Day. In fact, they barely lasted one day.

The recipe is a variation on my favourite chocolate molasses crinkle cookie made a little more decadent with the addition of a Rolo candy, which happens to be one of my kids’ favourite treats. (Both of my children inherited the caramel-lovers gene from me, handed down from my mom.)

I stumbled across the recipe in the December 2015 issue of Canadian House & Home Magazine. I didn’t quite get to them over Christmas so I tucked the recipe in my Valentine’s Day folder.

Caramel-Stuffed Chocolate Molasses Crinkle Cookies

You can bake the cookies with the Rolos stuffed inside, or placed on top, or do a bit of both. Tucked inside the caramels are like a hidden treat, a throwback to the days when we used to have wax paper wrapped coins in our birthday cakes.

With the Rolos placed on top, the cookies look irresistible. The only drawback is that the cookies are then vulnerable to having the Rolos plucked off the top.

Caramel-Stuffed Chocolate Molasses Crinkle Cookies


Caramel-Stuffed Chocolate Molasses Crinkle Cookie Recipe

Makes about 20 cookies


  • 1 ½ cups flour
  • 1 ½ tsp. ginger
  • 1 tsp. cinnamon
  • ¼ tsp. nutmeg
  • 1 Tbsp. cocoa powder
  • 1 tsp. baking soda
  • ½ cup butter, room temperature
  • 1 Tbsp. grated fresh ginger
  • 1/3 cup golden brown sugar
  • ½ cup Crosby’s Fancy Molasses
  • ½ cup dark chocolate chips or chopped dark chocolate
  • 20 Rolo candies
  • ¼ cup sugar (for rolling cookies in)


  1. Combine flour, spices, cocoa and baking soda in a bowl.
  2. In another bowl beat the butter and fresh ginger. Add the brown sugar and beat until well combined. Add the molasses and mix well.
  3. Stir the flour mixture into the butter mixture and combine well. Stir in the chocolate chips.
  4. Put the dough in the fridge for an hour (or overnight)

When you’re ready to bake your cookies, pre-heat the oven the 350 F…

Rolo in the middle method:

  1. Roll dough into 1 ½ inch balls, create a dent in the middle and push a Rolo into the dough. Reform the cookie around the Rolo and seal well and reshape the ball.
  2. Dip or roll in sugar and place on a parchment-lined cookie sheet, 2” apart.
  3. Bake 12-14 minutes, until the surface cracks. Let cool. 

Rolo on top method:

  1. Roll dough into 1 ½ inch balls, dip or roll in sugar and place on a parchment-lined cookie sheet, 2” apart.
  2. Bake 10 minutes, remove from the oven and make a dent in the middle of each cookie with a melon baller or teaspoon-sized measuring spoon. Sit a Rolo in the dent and return pan to oven for another 2-4 minutes to finish baking.

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Caramel-Stuffed Chocolate Molasses Crinkle Cookies

4 thoughts on “Caramel-Stuffed Chocolate Molasses Crinkle Cookies

  1. lynda says:

    This recipe makes me SMILE!! Maybe I just want chocolate :)
    I will be making these cookies for my Valentine.
    Thank you for the recipe. Yum!

  2. Alisha says:

    Hi there, wondering if this would work with margarine or coconut oil instead of butter?

    1. Hi Alisha, These cookies would definitely work with margarine. I have never tried the recipe with coconut oil so am not sure.

  3. Teresa says:

    I’m going to try with coconut oil!!

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