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Pumpkin Pie Cookies

These Pumpkin Pie Cookies are so festive and delicoius. This twist on a pumpkin thumbprint cookie will be a hit with the entire family.
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Course: Dessert
Cuisine: American
Prep Time: 30 minutes
Cook Time: 15 minutes
Cooling Time: 1 hour
Total Time: 1 hour 45 minutes
Servings: 36 Cookies
Calories: 242kcal
Author: Wendy


  • large disposable piping bag
  • Medium piping bag with a star tip
  • Mini leaf cookie cutters
  • two cookie sheets
  • silicone baking mats or parchment paper
  • mixing bowls
  • silicone brush
  • whisk
  • mixer



  • ½ Cup sweet cream butter room temp ½ C canola oil
  • ½ Cup pure pumpkin puree
  • 1 Cup white sugar
  • ½ Cup powdered sugar
  • ½ teaspoon pure vanilla extract
  • 2 eggs large
  • 4 Cup all-purpose flour
  • 1 teaspoon pumpkin pie spice
  • 1 teaspoon ground cinnamon
  • ¼ teaspoon baking soda
  • ¼ teaspoon cream of tartar
  • ¼ teaspoon salt

Pumpkin Pie Filling

  • ¾ Cup white sugar
  • 1 teaspoon ground cinnamon
  • ½ teaspoon salt
  • ½ teaspoon ground ginger
  • ¼ teaspoon ground cloves
  • 2 eggs large
  • 15 ounces Pure Pumpkin
  • 12 ounces evaporated milk


  • 1 Cup powdered sugar
  • 3 tablespoon whole milk
  • ¼ teaspoon pumpkin pie spice

Whipped Cream

  • 2 Cups heavy whipping cream
  • ½ Cup powdered sugar
  • 1 teaspoon pure vanilla extract


  • 1 small frozen pie shell
  • ¼ Cup white sugar
  • 1 teaspoon ground cinnamon
  • 1 egg
  • 2 tablespoon water



  • Preheat oven to 350 degrees and line two cookie sheets with a silicone mat or parchment paper
  • Using a large bowl, beat the butter, oil, pumpkin, sugar, powdered sugar, vanilla and eggs until combined
  • In a medium bowl, whisk the flour, pumpkin pie spice, cinnamon, baking soda, cream of tartar and salt
  • Gradually beat in the dry ingredients into the wet until combined and a dough forms
  • Using a small ice cream scooper, or tablespoon, scoop out about 2 tablespoon of dough onto the cookie sheet
  • Using the back of the tablespoon or your thumb, make a indent into the center of the cookie

Pumpkin Filling

  • Using a medium bowl, whisk together all ingredients of the pumpkin pie filling until smooth and combined
  • Scoop into the piping bag and cut the tip off
  • Pipe the filling into the indents of the cookies
  • Bake in the oven for 14-16 minutes or until the cookies are baked
  • Allow cooling completely


  • Unroll the pie crust onto a cutting board and cut out mini leaves and place onto the cookie sheet
  • Make an egg wash and brush the leaves with the egg wash
  • Mix the sugar and cinnamon together and sprinkle over the leaves
  • Bake in the oven for 8-10 minutes or until a golden brown
  • Allow to cool


  • Using a small bowl, whisk the ingredients for the glaze until combined and smooth Drizzle over the cookies

Whipped Cream

  • Using a medium bowl, beat all whipping cream ingredients together until stiff peaks start to form Scoop into the piping bag
  • Pipe dollops onto the center of the cookies and place a leaf onto the whipped cream Enjoy!


Don't overcrowd your baking pan, you don't want your cookies to touch when baking.
For best results make sure that your ingredients are room temperature before you start making cookies.
If you are using leftover pumpkin pie filling to make these cookies, skip the ingredients and steps to make pumpkin pie filling.


Serving: 1Cookie | Calories: 242kcal | Carbohydrates: 34g | Protein: 4g | Fat: 10g | Saturated Fat: 6g | Polyunsaturated Fat: 1g | Monounsaturated Fat: 3g | Trans Fat: 1g | Cholesterol: 50mg | Sodium: 127mg | Potassium: 107mg | Fiber: 1g | Sugar: 19g | Vitamin A: 2699IU | Vitamin C: 1mg | Calcium: 48mg | Iron: 1mg