Jack-o-lantern Cupcakes

These Jack-o-lantern cupcakes are inspired by a childhood memory of my Auntie Judy and my cousin Brad one fall day in Northern California when I was about seven years old. My sister, brother and I were staying over the weekend at our cousin's house, like we often did when we lived near by. We were looking for something to do and decided to rake up all the leaves from Brad's front yard. We might have been told to do it by my aunt, but either way we were quick to get to work. Brad had three, maybe four huge trees in his yard that would drop piles and piles of orange, red and brown leaves each autumn. The entire lawn was a sea of beautiful fallen leaves. All of us kids, including the neighborhood kids quickly raked them up into big piles and jumped and played in them. We fell backwards in them, hoping the pile was deep enough to not hurt our butts when we landed. We threw them at each other and stuffed them down the back of our coats;It actually gets cold enough for coats in Northern California. We threw them in the air and let them fall like confetti all around us as we laid on a soft crunchy bed of leaves. It was so much fun. After we cleaned up all the leaves we headed inside where my Aunt Judy was in the kitchen making cupcakes for Brad's classroom Halloween party. I remember those cupcakes like it was yesterday. She made these jack-o-lantern cupcakes with bright orange frosting and she cut up Hershey® bars into triangles that made up the eyes, nose and mouth with a small green frosting stem. I wanted to make some for my classroom too, they were so cute. I'm 48 years old and still think of that day and realize that it formed my love of the fall season and all things Halloween. Despite the fact that I now live in Southern California where it doesn't get cold in October and I don't have big trees that drop leaves on my front lawn, I take the warmth of that memory with me and let it feed my soul every Autumn. 🍂 🍁

Here's my slightly darker version of my Auntie Judy's Jack-o-lantern Cupcakes.
🎃🎃🎃 113 days until Halloween 🎃🎃🎃

Jack-o-lantern Cupcakes

Makes 12

1 box chocolate cake mix
1 prepared chocolate frosting* or homemade buttercream
black gel food coloring

Flooding Icing
1/2 cup powdered sugar
1/2 T milk (or more if needed)
orange gel food coloring

Prepare cake according to package directions. Add about 1/2 tsp black gel food coloring and mix until well combined.

Prepare a cupcake pan with 12 cupcake liners. Using a large scoop, fill cupcake liners about 3/4 full with batter. Next, spray a round cake pan with baking spray and fill with remaining batter. Cook both according to package directions. Remove from oven and let cool completely.

Frosting Prep
To prepared frosting, add a small amount of black gel food coloring and stir until well combined. Transfer frosting into a piping bag and refrigerate for about 30 minutes or longer to firm it up before frosting cupcakes.

*Note: I had some trouble with the frosting being too soft at room temperature which caused my jack-o-lantern toppers to slide off the cupcakes. It probably had to do with the temperature that day, it's summer🌞 afterall. So to avoid this, refrigerate the frosting as noted above or I recommend using a homemade buttercream frosting for a firmer frosting that'll hold up better.
Chocolate Buttercream Frosting
1/2 cup butter, room temperature
1 cup powdered sugar
2 T cocoa powder
1-2 T whipping cream
Cream butter, sugar and cocoa with a hand mixer. Add whipping cream and whip until smooth.

Cake pop Prep
Crumble the cooled cake from the round pan into a medium bowl. Add ~2 or 3 Tbsp of prepared frosting and mix well until it holds together when pinched between your fingers. Set aside.

I got these Wilton® jack-o-lantern molds ages ago, but you can get something similar like these from Wilton®. Press cake-pop mixture into molds, smoothing out the bottom. Refrigerate for 60 minutes until firm. Repeat to make 12 cake pops.

Gently press the back of the mold until the cake pop drops out of the mold. Place on wax paper. At this point you can either light up the jack-o-lanterns with orange icing and serve or refrigerate between wax paper until ready to assemble cupcakes.

Mix flooding frosting and put into a squeeze bottle with a small tip. Very carefully drop small amounts of flooding icing into eyes, nose and mouth of jack-o-lanterns. Careful not to overfill. Use a toothpick to gently spread icing into small corners of eyes, nose and mouth.

Let icing set about 25 minutes. The icing will never fully harden and after about a day the icing will fade into the cake pop. Kinda like the candle that burns out in real jack-o-lanterns, so make sure to serve these within a day of lighting them up. 🎃 Now we're ready to assemble...pipe a circle of frosting on cooled cupcakes...and then add a jack-o-lantern cake pop to the top. Happy Halloween!