I had the idea for these cupcakes over a year ago, and now I am wondering why it took me so long to make them. They were so very good! I normally try to keep my recipe names short, but this time there was really no way to shorten it without losing one of the things that makes these so great.

It all started on a drive to Asheville last year. It was the middle of fall and we were driving through the Smokies at just about the peak of fall color. The leaves were vivid shades of red, orange, and yellow and it was just gorgeous. So naturally, I was thinking of food. And not just any food – pumpkin treats. I had recently made pumpkin cookies with chocolate chips and had come to the same conclusion I often do with pumpkin/chocolate recipes: there was simply too much chocolate and it overpowered the pumpkin flavors. In fact, I make this great Harvest Cake that is chocolate with pumpkin cream cheese filling, covered in chocolate ganache. Yes, it is delicious, but I am always left wanting more pumpkin. So I started to think, what if I just made it pumpkin cake instead of chocolate? Would the ganache still be too much?

Then I had a brilliant flash. What if I made cupcakes, filled them with chocolate ganache, and used the pumpkin cream cheese filling as icing? I suspected this would be the perfect ratio of pumpkin and chocolate. Then I sat on the idea for a year. Last weekend, I finally decided it was now or never ,and I am so glad I finally made these! The ratio is perfect! Lots of great pumpkin flavor in both the cake and the icing, and just enough chocolate to make the perfect bite. Mmmm.

To create this perfect combo, I first made the The Brown Eyed Baker’s Pumpkin Cupcakes, which are simple and delicious. Once they were cool, I used a technique for filling cupcakes that I learned from a Baking Bites recipe for Vampire Cupcakes (which are also awesome for Halloween). You use a paring knife held at an angle to cut what is essentially a cone of cake out of the top of each cupcake, cut off the pointy end, fill the cupcake, and add the little cap back on top. The blog has a great tutorial and even a video if you need more guidance. Plus you get to eat the little extra bits of cake that you cut out to make room for filling! I then made the ganache and pumpkin cream cheese filling from my Harvest Cake and used the filling as icing. I am really bad at making icing look all fancy, so just pretend these are prettier. I guarantee that they taste good enough to make up for it!

Note that these do take some time, but not a ton. I made the cupcakes one evening and filled and frosted them the next night. But you could do this in one day if you made the cupcakes early enough. You just need time for them to cool. The filling step is really not that labor-intensive, as you can prep the cupcakes while waiting for the ganache to firm up a bit. These would be great for any fall party or a welcome addition to the Thanksgiving dessert line-up!