Thanksgiving Cookies With Pumpkin Pie Filling And Fall Shortbread

If you love pumpkin pie but want an easier, hand-held version that’s perfect for sharing, these Pumpkin Pie Cookies are your new fall obsession. Soft, buttery cookies are topped with a creamy pumpkin pie filling made with pumpkin purée, warm spices, and sweet vanilla — then baked until perfectly set and finished with a swirl of whipped cream. They taste just like a miniature pumpkin pie wrapped inside a chewy cookie. These cookies are cozy, festive, and incredibly simple to make, making them the perfect treat for fall gatherings, Thanksgiving dessert boards, bake sales, or anytime your pumpkin cravings hit.

Why You’ll Love Pumpkin Pie Cookies

These cookies capture the essence of pumpkin pie in a fun, portable form.

  • Soft, thick cookie base that stays tender for days.
  • Creamy pumpkin pie filling baked right on top.
  • Warm spices like cinnamon, nutmeg, and cloves in every bite.
  • Easy to make, no chilling or rolling out needed.
  • Perfect for parties, gifting, and holiday dessert tables.
  • Kid-friendly, freezer-friendly, and guaranteed crowd-pleasers.

Why You Should Try This Recipe

These cookies combine two fall favorites into one irresistible dessert — soft sugar cookies and creamy pumpkin pie filling. You get all the cozy flavors of classic pumpkin pie with half the effort and zero slicing. Plus, the visual appeal is stunning: golden cookies topped with a glossy pumpkin center and a whipped cream swirl. Whether you’re baking ahead or serving fresh from the oven, these cookies stay soft, flavorful, and delicious.

Ingredients You’ll Need

For the Cookie Base

  • ½ cup unsalted butter, softened
  • ½ cup sugar
  • ½ cup brown sugar
  • 1 egg
  • 1 tsp vanilla extract
  • 1 ¾ cups all-purpose flour
  • ½ tsp baking soda
  • ½ tsp baking powder
  • ¼ tsp salt
  • ½ tsp cinnamon

For the Pumpkin Pie Filling

  • ¾ cup pumpkin purée
  • ½ cup brown sugar
  • 1 egg yolk
  • ½ tsp vanilla extract
  • ½ tsp cinnamon
  • ¼ tsp nutmeg
  • ¼ tsp ginger
  • Pinch of cloves (optional)
  • 2 tbsp heavy cream

For Topping

  • Whipped cream or whipped topping
  • Cinnamon or nutmeg for dusting

How to Make Pumpkin Pie Cookies

  1. Preheat Oven: Set oven to 350°F (175°C) and line two baking sheets with parchment.
  2. Make Cookie Dough: Cream butter with sugars until fluffy. Mix in egg and vanilla. Add flour, baking soda, baking powder, salt, and cinnamon. Mix until a soft dough forms.
  3. Roll & Shape: Scoop dough into balls. Place on baking sheets and flatten slightly. Use a spoon or thumb to create a shallow well in the center of each cookie.
  4. Make Pumpkin Filling: Whisk pumpkin purée, brown sugar, egg yolk, spices, vanilla, and cream until smooth.
  5. Fill Cookies: Spoon a small amount of pumpkin filling into the center of each cookie well.
  6. Bake: Bake 12–14 minutes until edges are lightly golden and centers are set.
  7. Cool & Decorate: Let cookies cool completely, then top with whipped cream and a sprinkle of cinnamon.

Nutritional Information (Estimated per cookie)

  • Calories: 155
  • Protein: 2g
  • Carbs: 20g
  • Fat: 7g
  • Sugar: 12g
  • Fiber: 1g

Tips for the Best Pumpkin Pie Cookies

  • Create deep enough wells so the filling stays centered.
  • Avoid overfilling — filling expands slightly in the oven.
  • Use pumpkin purée, not pumpkin pie filling.
  • Allow cookies to cool before decorating to prevent melting.
  • Add a small swirl of whipped cream just before serving.
  • For extra flavor, add a pinch of pumpkin spice to the cookie dough.

Variations & Substitutions

  • Maple Pumpkin Cookies: Add 1 tbsp maple syrup to the filling.
  • Graham Cracker Twist: Roll the cookie dough balls in crushed graham crackers.
  • Cream Cheese Frosted Version: Top with cream cheese icing instead of whipped cream.
  • Extra Spicy: Increase cinnamon or add pumpkin pie spice.
  • Chocolate Drizzle: Add a thin drizzle of white or dark chocolate.

What to Serve with Pumpkin Pie Cookies

  • Hot apple cider
  • Pumpkin spice latte
  • Chai tea
  • Vanilla ice cream
  • Coffee or espresso
  • Fall dessert charcuterie boards

Common Mistakes to Avoid

  • Using too much filling: It may spill over during baking.
  • Overbaking: Cookies should remain soft — remove when edges are golden.
  • Watery pumpkin: If purée is too wet, blot with a paper towel.
  • Adding whipped cream too early: Add right before serving.

Storing Tips

  • Store undecorated cookies for 3–4 days in an airtight container.
  • Refrigerate decorated cookies for up to 2 days.
  • Freeze cookie bases (without filling) for up to 2 months.
  • Freeze fully baked cookies (without whipped cream) for up to 1 month.

Conclusion

These Pumpkin Pie Cookies bring together the warm spices of fall, the creamy richness of pumpkin pie, and the soft, buttery joy of a perfectly baked cookie. With their gorgeous presentation and melt-in-your-mouth texture, they’re a festive and delicious treat that’s perfect for any autumn occasion. Simple, cozy, and incredibly satisfying — these cookies are guaranteed to become a seasonal favorite.

Recipe FAQ’s

Can I use pumpkin pie filling instead of pumpkin purée?
No — it’s too sweet and will alter consistency.

Can I make the dough ahead?
Yes — chill up to 48 hours.

Can I freeze the cookies?
Yes — freeze baked cookies without whipped cream.

Can I use store-bought sugar cookie dough?
Yes — create wells and fill as directed.

Can I make these gluten-free?
Use a gluten-free 1:1 baking flour blend.

Do I need to refrigerate leftovers?
If topped with whipped cream, yes.

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