Upside-Down Pumpkin Filled Chocolate Cupcakes
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If you’re looking for a festive Halloween treat that’s equal parts spooky and scrumptious, these Upside-Down Pumpkin-Filled Chocolate Cupcakes are just the ticket! With rich dark chocolate cake, a creamy orange-hued pumpkin filling, and a glossy ganache topping, they’re a showstopper for any fall gathering. The best part? They start with a cake mix, so they come together quickly—perfect for busy bakers who still want to impress.
The filling is smooth and lightly spiced, giving just a hint of pumpkin flavor without overpowering the chocolate. And that ganache? It’s the finishing touch that takes these cupcakes from fun to fabulous—I’m a total ganache lover, so I may have gone a little extra with it. This recipe is adapted from a Paula Deen classic featured in the Sept/Oct 2009 issue of Cooking with Paula Deen, and I couldn’t agree more: pumpkin and chocolate are a match made in autumn dessert heaven.
Ingredients for Upside-Down Pumpkin Filled Chocolate Cupcakes
- DARK CHOCOLATE CAKE MIX (I USED DUCAN HINES DARK CHOCOLATE FUDGE, BUT I THINK A DEVIL’S FOOD VERSION WOULD ALSO WORK)
- LIGHT CREAM CHEESE
- CANNED PUMPKIN PUREE
- POWDERED SUGAR
- SEMI SWEET CHOCOLATE CHIPS
- HEAVY WHIPPING CREAM
Instructions for Upside-Down Pumpkin Filled Chocolate Cupcakes
Preheat & Prep – Preheat your oven to 350°F. Spray two 12-cup muffin pans with nonstick baking spray that includes flour. Skip the cupcake liners—these cupcakes are flipped upside down for serving! I just used my silicone muffin pans.
Bake the Cupcakes – In a large bowl, prepare a dark chocolate cake mix according to package directions for cupcakes. Divide the batter evenly between the muffin cups and bake as directed. Let cupcakes cool in the pans for 10 minutes, then carefully remove and place rounded side down on wire racks to cool completely.
Make the Pumpkin Filling – In a medium bowl, beat together the softened cream cheese, canned pumpkin, and confectioners’ sugar. Use an electric mixer on medium speed until the mixture is smooth and creamy.
Assemble the Cupcakes – Once cooled, slice each cupcake horizontally to create two layers. Spread about 2 tablespoons of pumpkin filling onto the rounded half of each cupcake. Top with the flat half, pressing gently to sandwich the filling.
Make the Ganache Topping – In a microwave-safe bowl, combine the chopped semisweet chocolate and heavy cream. Microwave on High in 30-second intervals, stirring between each, until the chocolate is melted and the mixture is smooth. Let cool slightly.
Finish & Serve – Spoon the ganache over the flat side of each cupcake, letting it drip slightly down the sides. Chill until set, or serve immediately for a gooey finish.
Frequently Asked Questions
Why are these cupcakes served upside-down?
Serving them upside-down lets the rounded cupcake top become the base, creating a flat surface for the ganache and a fun twist on presentation. It also makes the pumpkin filling peek out beautifully!
Can I use a different cake mix flavor?
Yes! While dark chocolate pairs wonderfully with pumpkin, you can try devil’s food, spice cake, or even yellow cake for a different flavor profile.
Do I need to use food coloring in the filling?
Not at all. The pumpkin naturally gives the filling a soft orange hue, but you can add a drop of orange food coloring for a more vibrant Halloween look.
Can I make these ahead of time?
Definitely! Assemble and chill the cupcakes up to 2 days in advance. Store them covered in the fridge until ready to serve.
Can I freeze these cupcakes?
It’s best to place them in the freezer unfilled and unfrosted. Once thawed, add the pumpkin filling and ganache fresh for best texture and flavor.
How do I cut the cupcakes in half without crumbling them?
Use a serrated knife and let the cupcakes cool completely before slicing. A gentle sawing motion helps keep the layers intact.
Is the ganache hard or soft once chilled?
The ganache firms up slightly in the fridge but stays soft enough to bite through easily. Let cupcakes sit at room temp for 10–15 minutes before serving for the best texture.
FOR MORE RECIPES LIKE THIS, TRY:
- Whipped Chocolate Ganache Frosting
- Chocolate Pumpkin Muffins
- Classic Pumpkin Chocolate Chip Muffins
- Pumpkin Cupcakes with Chocolate Frosting
Upside-Down Pumpkin Filled Chocolate Cupcakes
Real Mom Kitchen
Equipment
Ingredients
- 1 box dark chocolate cake mix I used Ducan Hines Dark Chocolate Fudge, but I think a devils food version would also work
- 6 ounces light cream cheese softened
- ¾ cup canned pumpkin puree
- 1 ½ cup powdered sugar
- 1 ½ cup semi sweet chocolate chips
- ¾ cup heavy whipping cream
Instructions
- Preheat oven to 350 degrees F. Spray 2 (12-cup) muffin pans with nonstick baking spray with flour. (Do not use paper liners. I used my Demarle pan)
- Prepare cake mix according to package directions for cupcakes. Let cool in pans for 10 minutes. Remove cupcakes from pans, and place, rounded side down, on wire racks to cool completely.
- In a medium bowl, beat cream cheese at medium speed with an electric mixer until creamy. Add pumpkin and confectioners’ sugar, beating until smooth.
- Cut each cupcake in half horizontally. Spread about 2 tablespoons pumpkin mixture evenly over cut side of rounded cupcake halves. Top with cut side of flat cupcake halves.
- In a medium bowl, combine chocolate and cream. Microwave on High, in 30-second intervals, stirring between each, until chocolate is melted and cooled. Spoon desired amount of chocolate over flat side of each cupcake. Cover, and chill, or serve immediately.
