Stuffed Chocolate Chip Pumpkin Molasses Cookies

I love when things show up in my inbox that I would really like to do.

Like… “Would you make us some cookies, using pumpkin and molasses, and we will pay you for it?”

Umm, yes.

Turns out this very thing happened a week or so ago, when I was asked by Grandma’s Molasses to create a molasses cookie recipe for them this holiday season. I jumped on it, of course, as you see, I already had a recipe in mind, and this little email was just the thing to push me over the edge to make it transpire.


I love whoopie pies. I especially love pumpkin whoopie pies, filled with a spicy cinnamon cream cheese. In fact, I showed up on Daytime Blue Ridge not too long ago making a version of these very cookies. Soft and sweet, spicy and rich – one bite and you’ll know why I get asked for them time and again.

They’re pretty incredible.

The addition of dark chocolate chips only intensifies the taste bud experience. Sure, you could leave them out, but why? Anything with chocolate is always better. Besides, chocolate and pumpkin are soul mates. They deserve to play together, and who are we to break up a match like that?

Give them a shot…I think you’ll love them.

Stuffed Chocolate Chip Pumpkin Molasses Cookies

makes 2 dozen


  • 3 cups plus 2 Tablespoons all-purpose flour
  • 1 teaspoon salt
  • 1 teaspoon baking soda
  • 1 teaspoon baking powder
  • 1 cup granulated sugar
  • 1/4 cup light brown sugar
  • 1/4 cup Grandma’s Molasses
  • 1 1/2 teaspoon ground ginger
  • 2 Tablespoons cinnamon
  • ½ teaspoon ground nutmeg
  • 1/2 cup light brown sugar, packed
  • 1/2 cup melted butter
  • 1/2 cup vegetable oil
  • 3 cups pumpkin puree
  • 2 large eggs
  • 2 teaspoons vanilla extract
  • 1 1/2 cups dark chocolate chips


  1. In a large bowl, whisk together the flour, salt, baking soda, baking powder, and spices. Set aside.
  2. In a Mixer Bowl, whisk the sugars, molasses, oil, and melted butter together. Add the pumpkin puree and combine thoroughly. Add the eggs and vanilla and whisk until combined. Pour the flour mixture over the wet ingredients and slowly whisk to combine. Do not overmix. Slowly stir in chocolate chips.
  3. Preheat oven to 350F. Prepare to baking sheets lined with parchment paper or a SilPat.
  4. Place entire mixer bowl in the refrigerator to chill for 20 minutes while oven preheats, then use a cookie scoop to make round cookies in about 2 inch circles onto prepared sheets. Bake for 13-15 minutes, or until cookies look done. Once cool, fill centers with cream cheese icing.

Cinnamon Cream Cheese Frosting

  • 1 stick butter, Room Temperature
  • 8 oz. Cream Cheese, Room Temperature
  • 3 1/2 cups Confectioners Sugar, maybe more
  • 1/2 tsp. Cinnamon
  • 1 tsp. Vanilla
  • Dash of Salt

Beat Cream Cheese, Butter, Salt & Cinnamon until lump-free and smooth. Gradually add sugar until well combined. Add vanilla until just incorporated. Pipe onto cookies and sandwich them together.


Grandma’s Molasses

Starting on Dec. 3rd, Grandma’s will launch a special application on Facebook that will showcase 12 featured recipes (mine is one!), will celebrate recipe sharing in general, and will kick-off a recipe submission contest for the public. Have a great molasses cookie recipe? You should enter! Stay tuned! Follow Grandma’s on Facebook for more details!

Disclaimer: This post was sponsored by Grandma’s Molasses. All thoughts and opinions are my own.

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