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Chocolate Dipped Pumpkin Whoopie Pies

​Chocolate Dipped Pumpkin Whoopie Pies are an out of the ordinary holiday treat! Can be served as a casual cookie or a dessert for your next holiday gathering. 

Course Dessert
Cuisine American
Keyword chocolate, pumpkin cookie, whoopie pie
Prep Time 20 minutes
Cook Time 10 minutes
cooling 15 minutes
Total Time 30 minutes
Servings 12
Author A Bountiful Kitchen


for cookie:

  • 2 eggs
  • 1 cup brown sugar
  • 1/2 cup canola oil
  • 1 cup canned pumpkin
  • 1 teaspoon vanilla extract
  • 2 1/2 cups flour
  • 1 teaspoon baking powder
  • 1 teaspoon soda
  • 1/2 teaspoon salt
  • 1 teaspoon ground cinnamon
  • 1/2 teaspoon pumpkin pie spice

for dipping:

  • 2 cups semi sweet chocolate chips melted

for filling:

  • 6 tablespoons butter softened
  • 3 cups powdered sugar
  • dash of salt
  • 3/4 teaspoon pumpkin pie spice
  • 1 teaspoon vanilla
  • 2-3 tablespoons cream milk or half and half


  1. Preheat oven to 375 degrees.

  2. In a large bowl, beat eggs and brown sugar until smooth. On low speed, mix in rest of wet ingredients. Scrape down sides of bowl.

  3. Add the dry ingredients to the bowl and mix all at once. Mix just until wet and dry ingredients are incorporated. Do not over mix.

  4. Spoon or scoop the batter out onto a parchment lined or lightly greased cookie sheet, about 9 cookies per sheet, taking care to form the cookies as uniform as possible*

  5. Bake until the tops feel firm about 10 minutes. Remove cookies from baking sheet and place all cookies in a single layer on a cool baking sheet. Place in fridge until cooled completely, about 10 minutes. 

  6. Meanwhile, melt chocolate in microwave for about 30 seconds, stir, repeat until chocolate chips are melted. Do not over heat, the chocolate will burn easily. Stir until smooth.

  7. When cookie are cool, spread about a teaspoon and a half onto the bottom of the cookie. Place back in fridge when all cookies are coated. Refrigerate for another 5-10 minutes or until chocolate is hardened. 

  8. While chocolate is setting up, make filling by beating all ingredients together until smooth, scraping down sides of bowl to incorporate all ingredients at least once. Beat for another minute until light and fluffy. 

  9. When chocolate is set, Spread filling onto the chocolate coated side of one cookie. Place another cookie on top to form a whoopee pie. Alternately, you may frost the top of the cookie and serve the cookie as a single piece with the chocolate dipped bottom and frosted top (see photo on post). 

  10. Refrigerate or store in cool place on counter, covered. 

Recipe Notes

  • I used a #30 scoop or a scoop that holds approx 2 tablespoons of dough. You may use a smaller scoop if desired, reduce the baking time accordingly. 
  • When covering, use parchment paper to cover the cookies so they won't stick to the top of the lid or cover. The cookies are very moist and will stick easily. 
  • This cookie needs to be cooked completely, no wet dough in the center. Do not under bake this cookie!