These Pumpkin Whoopie Pies are made with soft, cake-like pumpkin cookies sandwiched around a sweetened cream cheese filling.

They’re closer to a handheld cake than a cookie, with a filling thick enough to hold its shape between the two halves.

I make a batch of these for fall bake sales or just because the house needs to smell like pumpkin spice for an hour. They’re a little messy to eat, in the best way.

If you like soft, fall-spiced desserts like these, these are worth trying too:

Ingredients You’ll Need

Pure pumpkin puree keeps these cookies soft and cake-like instead of crisp, which is exactly the texture you want for whoopie pies.

Chilling the cream cheese filling briefly helps it hold together better once sandwiched.

Ingredients

2 cups all-purpose flour
1 tsp baking soda
1 tsp baking powder
2 tsp pumpkin pie spice
1/4 tsp salt
1/2 cup vegetable oil
1 cup packed brown sugar
1 cup canned pumpkin puree
1 large egg
1 tsp vanilla extract
8 oz cream cheese, softened
1/4 cup unsalted butter, softened
1 3/4 cups powdered sugar

Directions

Preheat your oven to 350°F and line two baking sheets with parchment paper.
In a medium bowl, whisk together the flour, baking soda, baking powder, pumpkin pie spice, and salt.
Set the dry mixture aside.
In a large bowl, whisk together the vegetable oil and brown sugar until combined.
Whisk in the pumpkin puree, egg, and vanilla until smooth.
Add the dry ingredients and stir just until no streaks of flour remain.
Drop rounded tablespoons of batter onto the prepared baking sheets, spacing them about 2 inches apart.
These spread a bit as they bake, so don’t crowd them too closely together.
Bake for 10 to 12 minutes, until the tops spring back when touched lightly.
Let the cookies cool on the pan for 5 minutes before transferring to a wire rack to cool completely.
This step matters more than it seems like it should – filling warm cookies melts the cream cheese filling right out of the sandwich.
Give them a full 20 to 30 minutes to cool before moving on.
While the cookies cool, beat the cream cheese and butter together until smooth.
Add the powdered sugar and beat until light and fluffy.
Chill the filling in the fridge for 10 minutes if it feels too soft to pipe or spread neatly.
Match the cooled cookies into pairs of similar size.
Spread or pipe a generous spoonful of filling onto the flat side of one cookie in each pair, then top with the second cookie, pressing gently until the filling reaches the edges.
Serve and enjoy!

Important Recipe Notes

Let the cookies cool completely before filling. Warm cookies melt the cream cheese filling instantly, leaving you with a soupy mess instead of a neat sandwich.
Match cookies by size before filling. Pairing similarly sized cookies gives you evenly shaped whoopie pies that sit flat instead of lopsided.

Don’t overbake these. They should look slightly underdone in the center when you pull them, since they continue cooking on the hot pan for a few minutes after.
Chill the filling if it’s too soft to work with. A softer filling spreads out the sides when pressed, so 10 minutes in the fridge firms it up for cleaner assembly.
Store assembled whoopie pies in an airtight container in the fridge for up to 4 days. They also freeze well for up to 2 months – thaw in the fridge before eating.
Freeze the cookies and filling separately if you want to make these ahead, and assemble fresh the day you plan to serve them.

How to Serve, Store & Customize This Recipe

Serving:

Serve these chilled or at room temperature as a fall treat with coffee or cider. They’re a little messy to eat by hand, so a napkin nearby is a good idea.

Storage:

Keep assembled whoopie pies in an airtight container in the fridge for up to 4 days. For longer storage, freeze for up to 2 months and thaw in the fridge before serving.

Customization:

Add a pinch of ground ginger to the filling for extra warmth, or roll the edges of the filled whoopie pies in chopped toasted pecans.

Swap the cream cheese filling for a marshmallow fluff filling if you want something sweeter and lighter.