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+ servings
dark chocolate cookies with orange icing and pumpkins and gummy worms

pumpkin patch dirt cookies;

Soft and slightly chewy uber dark chocolate cookies topped with a delightful pudding icing and topped off with dirt cookie crumbles, gummy worms, and candy pumpkins for a delightful Halloween pumpkin patch
Prep Time: 1 hour 15 minutes
Wait Time: 1 hour
Total Time: 2 hours 15 minutes
Oven Temp: 365°F
Servings: 30
5 from 1 vote
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Ingredients

oreo cookies;

  • cups unsalted butter (softened to room temperature)
  • cups light brown sugar (packed)
  • 1 cup granulated sugar
  • 2 large eggs
  • 1 Tbsp vanilla extract
  • 3 cups + 2 Tbsp all-purpose flour
  • 1 cup black cocoa powder
  • 12.08 oz Oreo crumbs - divided (I used 1 package of gluten free oreos, regular not double stuff, reserving roughly ¼ cup of crumbs)
  • tsp baking soda
  • 1 tsp baking powder
  • 1 tsp salt

pudding frosting;

  • 3.9 oz instant pudding (chocolate or vanilla)
  • 2 cups heavy cream (cold)
  • cup milk (cold, I used 2%)
  • cup powdered sugar
  • 1 teaspoon vanilla extract
  • cup Dutch process cocoa powder (for chocolate frosting)
  • orange food coloring or red + yellow food coloring (for vanilla frosting)

toppings;

  • gummy worms
  • ¼ cup oreo crumbs (remaining from cookie base)

Instructions

oreo cookie base;

  • Preheat oven to 365°F. Line a baking sheet with parchment, set aside.
  • In a large bowl, cream together 1½ cups softened butter, 1½ cups brown sugar, and 1 cup sugar until evenly mixed. Add in 2 eggs and 1 Tbsp vanilla, scraping down the sides of the bowl to make sure everything is evenly incorporated.
  • Add in 3 cups + 2 Tbsp flour, 1 cup black cocoa powder, and oreo crumbs (reserving roughly ¼ cup for topping later. Add in 1½ tsp baking soda, 1 baking powder, and 1 tsp salt. Mix to combine.
  • Portion the dough into large 2 Tbsp cookies and roll into balls. Stagger the balls on the baking sheet, making sure to leave plenty of room between each cookie. Press down on each cookie dough ball slightly to flatten. Bake for 10 -12 minutes, the edges will appear set but the centers should appear soft.
  • (Optional) Clean up the edges of your cookies. Use a very large round biscuit cutter or cookie cutter, big enough to surround the cookie and still have some space left over. Gently move the cutter in a circular motion (think hula hoop) to help tuck the edges into a nice round shape.
  • Remove from the oven and let cool on pan for 5 minutes then transfer to parchment paper or a rack to cool completely.
  • Best served fresh, but cookies can be frozen in an airtight container (I've used ziplock bags doubled up with air pressed out of both) for up to a month, and thawed in the fridge overnight when ready to serve.

pudding frosting;

  • Chocolate pudding frosting (only): Combine 2 cups heavy cream, ⅓ cup cold milk, ⅔ cup powdered sugar, 1 tsp vanilla, ⅓ cup Dutch-processed cocoa powder, and one 3.9oz instant chocolate pudding mixture in a large bowl. Using a hand or stand mixer, beat until smooth and thickened.
  • Orange vanilla pudding frosting (only): Combine 2 cups heavy cream, ⅓ cup cold milk, ⅔ cup powdered sugar, 1 tsp vanilla, ⅓ cup Dutch-processed cocoa powder, and one 3.9oz instant vanilla pudding mixture in a large bowl. Using a hand or stand mixer, beat until smooth and thickened. Add in orange (or red + yellow) food coloring and mix until desired color is achieved, adding more color if needed.
  • Both chocolate and orange vanilla pudding frosting:
    Combine 2 cups heavy cream, ⅓ cup cold milk, ⅔ cup powdered sugar, 1 tsp vanilla in a large bowl. Using a large hand or stand mixer, beat until smooth. Remove half the mixture to a separate bowl.
    In one bowl add in ~2oz chocolate pudding mixture (half the box) and 2½ Tbsp cocoa powder and beat with mixer until smooth and thickened.
    In the second bowl add in ~2oz vanilla pudding mixture (half the box) and add orange (or red + yellow) food coloring and beat until smooth and thickened. Add more food coloring and re-mix if needed to achieve desired color.
  • Pudding frosting can be made in advance and stored in an airtight container or pastry bags in the fridge for up to 3 days.

dirt cookies;

  • Start assembly by frosting the cookies. For a rustic look, you can just spoon icing onto each cookie. For a more polished look, transfer frosting to a pastry bag with a tip of your choice and pipe icing onto each cookie in a spiral.
  • Assemble the toppings by sprinkling reserved crushed oreos on each frosted cookie as "dirt". Decorate with gummy worms and candy pumpkins as desired.
  • For best results (in my opinion) frost and serve cookies within 24 hours so the cookies retain a little bit of chew.
    If planning to assemble in advance, frost the cookies and sprinkle with oreo "dirt". You can store frosted cookies in the fridge for up to 3 days, but the cookies will soften as they sit. Wait to add gummy worms and pumpkins until just before serving or they may bleed colors on your icing.
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