Cupcakes · Recipes · Treat Day!

Chocolate Cherry Pie Cupcakes

So if you are a baker, I bet you also have that ONE recipe that you can always fall back on to be a crowd favorite. Well, this chocolate cherry pie cupcake has never ever failed me. This is the cupcake I take most to parties and potlucks, give as a gift, and get requested the most often. I love it because it has so many components and seems complicated, but it is super easy and quick! I mean, we are talking about baking a mini pie and placing it inside a mini cake. Duh, that is going to be heaven. I have done a few variations over the years like apple pie inside a vanilla cupcake, pear pie inside a spice cupcake, and a pecan pie inside a yellow cupcake, but the cherry pie/chocolate combination is hands down, the one people fawn over. Oh wow, I just remembered something. I baked 100 of these for my own wedding over 3 years ago…

Ryan just celebrated his 27th birthday and I told him he could have whatever he wanted and this cupcake was an easy choice for him. Best of all worlds. Cinnamon whipped buttercream. Moist chocolate cake. Cherry pie, crust and all. I made 24 and he ate at least 12 so far. In 3 days. I should probably make him stop. It is a really good thing I gave 5 away. I limited myself to 4, 2 of them without the frosting. I basically ate whatever I wanted for 7 days straight due to Mexico so as of today, no more cupcakes!!! I am trying to be okay with it.

The chocolate cake is super easy to throw together and has a really light, delicate crumb. The batter is pretty runny which makes it super easy to pour over the mini cherry pie. I use this chocolate cake recipe all the time. I found it in a Taste of Home recipe book a long time ago and although it isn’t as intensely chocolately as the other recipe I use, it is perfect for when the chocolate needs to share the spotlight with pie. Don’t let the simplicity fool you, it is completely ideal and has great flavor and texture.

As for the cherry pie, I say simple does it. You buy a package of refridgerated pie crust and a can of cherry pie filling. If you are fancier than me, please feel free to make your own! I am all about baking from scratch, but sometimes you need canned filling/frosting or boxed brownies/cake. It satisfies a completely different part of your brain and stomach.

The frosting is made using my #1 go-to buttercream recipe with a little cinnamon added. This is the only recipe I use for classic buttercream. It is quite annoying that it requires a few tablespoons of heavy whipping cream so I try to make sure I have another use for the cream as well. The heavy whipping cream is what makes the texture lighter than any other buttercream though. This recipe comes from America’s Test Kitchen and if you make it, you will just know that it is professionally tested. Not sickly sweet and not like eating a stick of butter on a cupcake. Only thing I can think of that would be better is fresh whipped cream! I will have to try that the next time someone requests these!

Chocolate Cherry Pie Cupcakes

Makes 24 cupcakes

Mini Cherry Pies

  • 1 package of refrigerated pie crust (the kind that you just unroll)
  • 1 small can of cherry pie filling
  1. Preheat the oven to 425 degrees.
  2. Roll out your pie crust on a flat, clean surface and cut out 24 medium round circles. I use a 1/3 measuring cup but you can use anything that cuts out circles that will fit nicely into a mini cupcake pan. Lightly press the crust into the mini cupcake cavity. No need to oil or butter the pan!
  3. Place 3 cherries inside each mini cupcake crust. Save the remaining cherry pie filling for decoration.
  4. Cut out 24 small circles of pie crust that will just cover the mini pies. I use a 1/8 measuring cup, but a shot glass works too! Using a little bit of water on the edges of the small crust, stick the top crust to the rest of the pie and lightly press to seal edges.
  5. Using a sharp knife, cut a slit into the top crust to let hot steam escape while baking.
  6. Bake the mini pies for about 18 minutes. They should be slightly golden brown. They might not be pretty but that is okay as they are going to placed inside cake batter. They should pop out very easily. Let them cool. Image (1)

Chocolate Cupcake

  • 1 cups all-purpose flour
  • 1 cups sugar
  • 1/3 cup baking cocoa
  • 1 teaspoons baking soda
  • 1/2 teaspoon baking powder
  • 1/4 teaspoon salt
  • 1 egg
  • 1/2 cup milk
  • 1/3 cup canola oil
  • 1 teaspoon vanilla extract
  • 1/2 cup brewed coffee
  1. Stir together flour, sugar, cocoa, baking powder, and baking soda in a large bowl. Add the egg, milk, oil, vanilla in and whisk until all combined. Add the coffee and stir well. Preheat oven to 350 degrees.
  2. Line 2 cupcake pans with 24 liners. Put just enough cake batter in each liner to cover the bottom. Place a cherry pie inside each. Pour the chocolate batter over the mini pies just until the cherry pie is barely covered (sell photos below). This fills the cupcake liner to a little over 3/4. This is okay because the cherry pie part does not rise. Getting the perfect amount of cake batter in might take some finesse, but gets easier. If you are worried about overfilling, use a spoon to put the cake batter in the cupcake liners. These cupcakes do not puff up like crazy, but if you over fill, they will spread out and be harder to take out of the pan. You may have a tiny bit of leftover batter (enough for like 1 full chocolate cupcake). Don’t try to add it to the 24 pie cupcakes!
  3. Bake for 15 minutes. Let cool on a rack.


Cinnamon Whipped Buttercream

  • 3 sticks of unsalted butter, at room temp
  • 1/4 tsp of salt
  • 2 tsps of vanilla extract
  • 3 tablespoons of heavy whipping cream
  • 3 cups of powdered sugar
  • 1/2 tsp cinnamon (less if you want the cinnamon very subtle!)
  1. Using a stand mixer and the whisk attachment (very important!), whisk the butter, salt, and vanilla on medium speed for 30 seconds or until incorporated well.
  2. Add the 3 TB of heavy whipping cream and whip on medium-high for 2 minutes.
  3. Slowly add the powdered sugar until just mixed. Don’t overbeat at this point. Stir in cinnamon.
  4. Pipe onto cupcakes. If you are not going to pipe, and are just going to spread on the frosting, you can cut this recipe down to 2/3. Getting a pretty rose takes more frosting. Use your leftover cherry filling to decorate.

And obviously, we are back from Cancun! I wish I could describe what an amazing vacation this was, but then I would get really depressed that I wasn’t still there. So I am going to put up some photos and hope you have or will experience the wonderment that an all-inclusive resort in Mexico can provide.

I am so so so glad I slimmed down a bit for this trip. It was a great way to mark a successful 3 months of healthy living. Although I still don’t love how I look in a bathing suit, I am really proud of myself when I look at some of the photos we took because I can truly see the difference in my body from “before”.


As you can tell by the photos though, the non-stop access to alcoholic beverages was just nuts. I mean we are talking strawberry margaritas, banana skydives, mojitos, and pina colados when-freaking-ever. That plus all-you-can-eat and room service. So yeah… I weighed in at 168 before we left and 170 since we got home! 2 lbs of bloated excess and fun. Considering how much we ate and drank while laying by the pool, I am lucky I didn’t gain more. It was really hard to stop that mentality once we got home too so I just didn’t.

But that’s okay! I am going to be okay! Today, I went back to work and got back on my healthier schedule. Had my Shakeology for lunch and I think for this week at least, I need to go back to intermittent fasting. I am making lettuce wrapped tacos for dinner and have shopped and planned out healthy eating for the rest of the week. Next step: I need to make sure that the next thing I post is not a recipe for cupcakes… It needs to be like protein or a salad. Time to start working on my next goal!


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