Headless Horseman Cupcakes for The Legend of Sleepy Hollow

“You can’t reason with a headless man.”

Happy Halloween! It’s 1989 and your 3rd grade teacher Mrs. Merritt is wiping clean the transparency filled with math equations and pushes the overhead projector out of the way. That creaking noise coming down the hall can only mean one thing. It’s video day! The TV cart is being wheeled into your classroom with the trusty VCR on the rack below. Best. Day. Ever. And since it’s October 31st there is only one movie to be played – The Legend of Sleepy Hollow. Bing Crosby’s sweet baritone voice will soon be filling your ears. That unlikely ladies’ man, Ichabod Crane, will be dancing (and mostly eating) before your eyes. Happy Halloween indeed.

We watched this classic Disney cartoon practically every October in elementary school. I had not watched the short movie in (I don’t want to do the math) some years. Upon my most recent viewing I was a little taken a back by all the alcohol consumption. I shouldn’t have been surprised though. Remember Dumbo? Or Gaston? Old Disney movies are filled with substance abuse. Thanks to mancouch.com I was able to find statistics like “out of 24 G-rated Disney films” there were 275 alcohol related instances. Not sure what that means, but that’s your information to live with now. The cartoon is actually more funny than scary, so at least Disney got that right. Despite the ominous ending, you’re laughing the whole time the Headless Horseman is after poor, lankly Ichabod Crane. I cannot say the same for Tim Burton’s version. While Johnny Depp is often humorous there were many moments of that film I watched through my fingers. Not sure why? Please refer to this post.

After living in New York City for several years, I felt silly to discover on an Amtrak train ride to Albany that I lived so close to the real life Sleepy Hollow. It’s a quiet, secluded location just outside Manhattan. There once existed a real man named Ichabod Crane. Except he wasn’t a superstitious school teacher, but a military Colonel. The history is actually pretty fascinating and is documented well here.

If you’d like to reminisce to a time when the sound of approaching horse hooves sent chills up your spine then look no further.

Let’s bake a movie…

Headless Horseman Pumpkin-Spiced Latte Cupcakes with Caramel Butter Cream

These cupcakes probably look more delicious than menacing, which I guess is never a bad thing when it comes to desserts. Thanks to my husband who ground up our fall flavored coffee beans the cake has a wonderfully abundant flavor of sweet pumpkin spices and a hint of acidic coffee. A happy marriage will be in your mouth. The luxuriously smooth caramel flavored butter cream on top makes you think you’re actually biting into that famous seasonal latte. That is, of course, if you can get past the ghoulish (yet tangy) eyes of the Headless Horseman.


For the cupcakes:
2 2/3 cups flour
3 tbsp. espresso powder (I used Pumpkin-spiced but any flavor will do)
2 tsp. baking soda
2 tsp. baking powder
1 tsp. cinnamon
1/8 tsp. ground nutmeg
¼ tsp. ground cloves
1 tsp. Salt
15 oz. can of pumpkin puree
1 cup brown sugar
1 cup granulated sugar
1 cup vegetable oil
4 large eggs, room temperature
Special tool: silicon mini bunt cups or pan

For the frosting:
3 sticks unsalted butter, room temperature

4 large egg whites
1 tsp. vanilla extract
Caramel sauce, smooth and from a squeeze bottle


1 yellow Starburst


Preheat oven to 350˚ F.

1) For the cake, using a whisk sift together flour, espresso powder, baking soda, baking powder, cinnamon, nutmeg, cloves and salt in a bowl. Set aside. In the bowl of an electric mixer, add pumpkin, brown sugar, granulated sugar and oil. Blend together on medium. Add eggs one at a time, beating until each are incorporated. Switch blender to low and add dry ingredients in two additions, mixing until just incorporated. Be sure to scrape down the sides, if necessary. Spray bunt cups liberally with non-stick cooking spray. Fill bunt cups no more than 2/3 of the way with batter. Bake in the over for 20-22 minutes, or until a tooth pick inserted in the center comes out clean. Let cupcakes cool in bunt cups for 10 minutes on wire rack. Then remove cupcakes to cool completely on rack.

2) For the frosting, cream butter with mixer until light and fluffy (about 2 mins). Set aside. Place a heatproof bowl over a pot of simmering water. Make sure the bowl is not touching the water. Whisk the egg whites and sugar in the bowl frequently, until the mixture reaches 160° F and the sugar has dissolved.  You should feel no grains of sugar when you rub mixture between your thumb and finger. In a standing mixer fitted with the whisk attachment, beat the egg mixture on medium-high speed until stiff peaks form. Allow the bowl to become cool to the touch (about 10 mins). Reduce speed to medium-low and begin to add creamed butter 2 tbsp at a time, mixing well after each addition. Mix in the vanilla. Switch to the paddle attachment. With the mixer on low, slowly add the caramel sauce in a long and steady stream. Add enough caramel to your level of taste. Careful not to add too much, it will flavor the butter cream quickly. Separate the frosting evenly into two small bowls. In one bowl add several drops of yellow food coloring till the desired yellow is achieved. In the second bowl add 5 drops of yellow for every 1 drop of red until desired orange is achieved. Transfer frosting to two different piping bags fitted with different sized star tips.

3) To assemble, slice the bottoms of two cupcakes to make a flat surface to balance one on top of the other. Place one cupcake top side down and place the other cupcake on top so that both smooth sides are touching. Pipe yellow and orange “flames” on top of the assembled cupcake. Heat unwrapped yellow Starburst in the oven for 5 seconds till softened. Flatten Starburst with fingers and cut out eyes, nose and teeth with a small pairing knife. Apply the eyes, nose and teeth to the side of the cupcake using a tiny bit of frosting as glue.

Source: Cupcakes from Annie’s Eats; frosting from Martha Stewart