Tuesday, July 10, 2018

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. πŸ‚ 🍁

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

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. πŸŽƒ  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!

Other Halloween desserts:
Candy Corn Peppermint Patties
Skull and Crossbones Cookies
Black Magic Spellcakes


  1. such happy little Jack cupcakes. I couldn't stop myself from smiling when I found this post. thank you so much for sharing.

    1. Thank you so much Rhonda! I'm glad they made you smile! I loved making them. Happy HAlloween!

  2. These are fantastic!! Thanks for this... I too had amazing times with my cousins and aunts and love how those memories shaped my world.

    1. Thank you for sharing your thoughts Tracy. I like to think that our cousins are our first best friends. Happy Memories and Happy Halloween!

  3. Hey Lori! LOVED the cupcake recipe and FYI - found the Wilton Jack o' Lantern molds like the ones used in the post on Amazon: https://www.amazon.com/gp/product/B0083G7OBQ/ref=oh_aui_detailpage_o01_s00?ie=UTF8&psc=1 (in case you want to update your post) Can't WAIT to make these for Halloween! Thanks for the terrific share...

    1. Thank you so much LilTexasRancher! I'm glad you found the molds, I'll update the blog with your link. :) Happy Halloween!

  4. These are truly adorable, but when I saw the mold you were using for the topper, I thought "She should totally make the black cats!!" :D

    1. So happy that you liked them! Yes, I agree, it was a really hard decision between jacks or cats...but either one would work with this cake pop idea. I'm playing around with the idea of cats for next year's theme, so don't be surprised if Cat Cupcakes make their appearance. Thank you for commenting. :)

  5. Hi! Thank you for posting this they look fantastic!
    I have a question though, I bought the Wilton Jack O Lanterns, no cats just 6 Jack O Lanterns and after I filled one I set it aside for 5 or so minutes and popped it out, I cannot see the indentations so could fill. Does freezing help that or am I doing something wrong?

    1. Yes, I would make sure you press in the cake and frosting mixture into the mold well and then refrigerate for about 30 minutes or longer so the frosting in the cake mixture firms up. Then gently tap out your cake pops onto wax or parchment paper and fill the eye nose and mouth with your icing. I imagine you could freeze it to speed up cooling, but I'd be careful not to freeze completely as it might crack the mold when you try to tap them out. Let me know if you have success. :)

  6. These look so great! I have a quick question. Can the jack o lanterns be served on their own, or will they be to soft to pick up? I plan on making them for a company party.

    1. Yes, they can be served by themselves. They are pretty dense and stay together well. Let me know how they turn out! Happy Halloween.