These Soft Baked Pumpkin Molasses Chocolate Chip Cookies are the rustic, delicious dessert you were hoping for this season. Rolled in cinnamon-sugar before baking and full of chocolate, they are going to stand out at all your gatherings.

Pumpkin Chocolate Chip Cookies
Pumpkin added to baked goods should not be left to just the Fall season. Pumpkin adds this magical quality to desserts unlike other vegetable additions we often throw into our baking creations. It’s just so good.
One of my favorite baking tricks is adding pumpkin to brownies, because pumpkin and chocolate are just the best pairing on the planet. Pumpkin also turns your coffee cake into perfection and has the best impact on breakfast muffins too. I won’t even mention how good pumpkin is in a smoothie. I need to use it more throughout the year.
For those of you who have been around this blog for a while, you know I am obsessed with making the best looking and tasting cookies, which is why I bake my cookies in whoopie pie pans. They turn out perfect every time; round, pretty, tasty and soft.
I weigh every single one of my cookie balls with a baking scale so they all cook evenly and fill each well of the pan. Perfect rounds! I also press on extra chocolate chips to the surface of each raw cookie ball as these chips do not sink inside while baking. Presentation is everything right?
These cookies are delicious enough to be served throughout the season (even Christmas) and will make the perfect addition to the holiday, dessert buffet table. They are also rustic enough to make an appearance at all your tailgating festivities this Fall.
All three dozen of these cookies disappeared at a little teenage study party that was happening over here the other night. I just can’t seem to keep them in stock once they emerge from the oven.
Soft Baked Pumpkin Molasses Chocolate Chip Cookies
Ingredients
Cookie:
- 2-1/2 cups all-purpose flour
- 2 teaspoons baking soda
- 1/2 teaspoon table salt
- 2 teaspoons pumpkin pie spice
- 1/4 teaspoon ground cinnamon
- 1/4 teaspoon ground ginger
- 1/2 cup packed light brown sugar
- 1/2 cup granulated sugar
- 1 stick (4 oz) butter
- 2/3 cup (4 oz) shortening (butter or regular flavored)
- 1 large egg
- 1/2 cup pumpkin puree
- 1/4 cup molasses
- 1-1/2 teaspoons vanilla extract
- 2 cups, plus more semi-sweet chocolate chips
Cinnamon Sugar:
- 2/3 cup granulated sugar
- 1 Tablespoon ground cinnamon
Directions
- Preheat oven to 350 degrees F. Prepare whoopie pie pans with cooking spray.
- In a medium bowl, combine flour, baking soda, salt, pumpkin pie spice, ginger and cinnamon. Set aside.
- In the bowl of a stand mixer, cream together both sugars, butter and shortening until light and airy; about 4 minutes. Add egg, pumpkin puree, molasses and vanilla and mix until fully combined. Stop mixer and scrape down the edges of the bowl. Slowly add in flour mixture and mix well. Stir in chocolate chips on low speed.
- In a small coll make cinnamon sugar mixture. Set aside.
- Roll dough into balls (36 grams or 2" in size). (This cookie dough is very wet/sticky..I prefer to use gloves while working with it.) Roll each ball in the cinnamon-sugar mixture and place one dough ball into each well of the whoopie pie pan. Press on about 8-10 extra chocolate chips into each dough ball (this is strictly for looks). Repeat until all the dough is used.
- Bake for 12 minutes and remove from the oven. It's okay if cookies are not completely finished, they will continue cooking out of the oven. Leave in the pan for 10 minutes before removing to a wire rack.
- Notes: You can use all butter in these cookies (8 oz) and omit the shortening. However, your cookies will be crispier in texture and not as lofty. If you decide not to bake these in a whoopie pie pan you will need to chill your dough for several hours before baking. I would suggest sticking with the shortening if you go this route. An all butter cookie melts very fast in the oven and will be very flat.
Other Pumpkin Cookies You Might Enjoy:
- Pumpkin Cheesecake Cookies
- Pumpkin Snickerdoodles
- Pumpkin Sugar Cookies
- Gooey Butter Pumpkin Cookies
- Pumpkin Maple Cookies
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- Four Years Ago: Quick and Easy Pickled Sandwich Onions
- Six Years Ago: Peanut Butter, Celery and Raisin Sandwich