When the air gets crisp and leaves start crunching underfoot, it’s time to whip up a batch of pumpkin whoopie pies. These pillowy soft pumpkin cookie sandwiches are packed with cozy spice and filled with a decadent maple cream cheese filling that melts in your mouth. Whether you’re after a festive pumpkin dessert recipe or simply craving homemade whoopie pies, this treat delivers all the autumn vibes in one sweet, nostalgic bite.

Why You’ll Love This Pumpkin Whoopie Pie Recipe

This isn’t your average cookie. Think soft, cake-like cookies spiced with pumpkin pie seasoning and sandwiched around the creamiest maple frosting you’ve ever tasted. The filling is smooth and tangy with just the right touch of sweetness, making these fall cookie sandwiches impossible to resist. They’re perfect for Halloween parties, Thanksgiving dessert tables, or just a cozy baking day at home.

Ingredients You’ll Need

Pumpkin Cookies:

3 cups all-purpose flour (375 g)
1 tsp salt
1 tsp baking soda
1 tsp baking powder
2½ tbsp pumpkin pie spice
1 cup granulated sugar (200 g)
1 cup packed dark brown sugar (220 g)
1 cup vegetable oil (240 ml)
3 cups chilled canned pumpkin puree (675 g)
2 large eggs
1 tsp vanilla extract

Maple Cream Cheese Filling:

3 cups confectioners’ sugar (360 g)
½ cup unsalted butter, room temperature (113 g)
8 oz cream cheese, room temperature (226 g)
3 tbsp maple syrup (45 ml)
1 tsp vanilla extract
Sprinkles or jimmies (optional)

How to Make Pumpkin Whoopie Pies

Preheat and Prep: Preheat oven to 350°F (175°C). Line two baking sheets with parchment or silicone mats.
Mix the Dry Ingredients: In a medium bowl, whisk together flour, salt, baking soda, baking powder, and pumpkin pie spice.
Mix the Wet Ingredients: In a large bowl, whisk together granulated sugar, brown sugar, and oil. Add pumpkin puree, eggs, and vanilla. Mix until smooth.
Combine: Add dry mixture to the wet ingredients and stir until fully incorporated with no flour streaks.
Scoop and Bake: Using a 1.5–2 tablespoon scoop, portion the batter onto prepared baking sheets about 1 inch apart. Bake one tray at a time for 10–12 minutes or until a toothpick comes out clean. Let cool 10 minutes on the tray, then transfer to wire racks.
Make the Filling: In a mixer, beat butter until creamy. Add cream cheese and beat until smooth. Add powdered sugar, maple syrup, and vanilla, and beat until fluffy. If the filling is too soft, chill for 30 minutes before assembling.
Assemble the Whoopie Pies: Pipe or spoon filling onto the flat side of half the cookies. Top with the remaining cookies and press gently to create sandwiches. Add sprinkles if desired.
Chill Before Serving: Refrigerate the assembled whoopie pies for at least 1 hour to set.

Tips for the Best Homemade Whoopie Pies

Chilled pumpkin puree helps give the cookies a thicker texture and better shape.
Don’t overbake—the cookies should be soft and tender.
For neat assembly, use a piping bag or zip-top bag with the corner snipped.
Store chilled in an airtight container and let sit at room temp for 10–15 minutes before serving.

A Slice of Pumpkin-Spiced Nostalgia

Pumpkin whoopie pies are more than just a pumpkin dessert recipe—they’re a celebration of fall flavors and homemade joy. I first made these on a rainy October afternoon with my kids, and they’ve been a seasonal must-have ever since. Whether you’re sharing them with friends or sneaking one with your morning coffee, they bring a smile with every bite.

What to Serve with Your Fall Cookie Sandwiches

These treats pair beautifully with hot apple cider, pumpkin spice lattes, or a cup of chai tea. Serve them on a platter with other fall favorites like maple pecan bars or caramel apple slices for a festive dessert spread.

How to Store Pumpkin Whoopie Pies

Keep assembled pies in an airtight container in the refrigerator for up to 5 days. For best texture, allow them to soften slightly at room temperature before serving. You can also freeze unassembled cookies and thaw before filling.

FAQs

Can I freeze pumpkin whoopie pies?

Yes! Freeze the cookies and filling separately, then assemble after thawing.

Can I make them smaller?

Absolutely—just reduce the baking time slightly and use a smaller scoop.

Can I use homemade pumpkin puree?

Yes, but make sure it’s well-drained to avoid soggy cookies.

What if I don’t have maple syrup?

You can substitute with honey or a splash of vanilla, but maple adds that distinct fall flavour.

The Sweetest Taste of Fall

These pumpkin whoopie pies are the kind of dessert that makes you want to cozy up in a sweater and watch the leaves fall. With spiced cookies and maple cream cheese filling, they’re festive, fun, and full of flavour—just the thing to sweeten up your season.

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