Old Fashioned Cupcakes

When I say these are old-fashioned cupcakes, I don’t mean old-fashioned like Grandma used to make. Unless Grandma was a whiskey-shooting wild child who liked taking her crazy ideas to the stand mixer so she could have her cake and drink it, too. In which case, yeah, they’re that kind of old fashioned. It’s the kind of grandma I’d want to be.

You might want to order another round.

You can bet your booty there’s bourbon in here— or, in this case, Gentleman Jack whiskey (I’ll explain this choice in a moment). And the frosting? Also boozy, with a generous splash of blood orange bitters and a shot of caramel flavor. Garnished with a candied orange wedge and a cocktail cherry, of course.

For best results, add the cherries just before serving.

I started thinking about these when I baked this year’s batch of mint julep cupcakes for Kentucky Derby, and I will admit that the result of these old fashioned cupcakes exceeds even what my taste buds imagined. They really do taste like the cocktail! The best thing about them is that, despite the complex flavor arrangement, they are surprisingly easy to make. 

What goes into an Old Fashioned cupcake?

For these grownup-only treats, I followed the formula template of my mint julep cupcakes, but with different flavor enhancers. Butter, brown and white sugars, eggs. And then the old fashioned flavors, in the form of orange zest, cocktail cherry syrup and (obviously) the whiskey. Alternate the addition of dry and wet ingredients, a bit at a time, to ensure even mixing; too much of either at once and you’ll end up overmixing the batter.


As an aside, do you see what my KitchenAid did with the zest? I guess it’s best to stir that in by hand at the end! Divide the batter evenly among the cupcake liners and bake, then cool for a bit before transferring them to a wire rack.


Why whiskey rather than bourbon?

We’ve enjoyed many a cocktail with Gentleman Jack, and I got curious what kept it from being labeled as bourbon. It is, after all, 80% corn and aged in oak barrels, and obviously produced in the U.S., so it certainly qualifies to be called “bourbon,” but the folks at Jack Daniel’s like to point out that their whiskey is charcoal-mellowed, and they consider it to be superior in every way to bourbon.

I don’t necessarily agree, but Gentleman Jack is very easy on the palate, and lower proof (80) than most of the bourbons we usually drink, which makes it lovely with the sweetness of dessert. Boozy, but no harsh bite. Now, let’s talk about the caramel notes in this buttercream!

The icing on the (cup)cake

Buttercream is not as difficult as I once feared—at least, not the kind I make. The butter should be softened at room temperature for about half an hour, so that you can press a fork or finger into it and leave an indent without the butter losing its shape. I use salted butter to accent all the other flavors.

For an “old fashioned” vibe, I spiked the butter with dulce de leche to accentuate the warm caramel flavors of the whiskey. Whip those together with an electric mixer until it is soft and fluffy before adding the sugar. If you go too far with powdered sugar, you can smooth it out again with a few drops of cold heavy cream. You want it swirly, but stable.


The finishing touch for my old fashioned cupcakes was a drizzle of Gentleman Jack and a spoonful of Stirring’s blood orange bitters. These are sold in a larger bottle than typical bitters, and they’re non-alcoholic, which makes them less intense. This is what really gives a “cocktail” flavor to the cupcakes, perhaps even more so than the star ingredient of whiskey. If you can only get regular, alcohol-based bitters, use half as much.


Decorating the cooled cupcakes is easy as well, and if you don’t have a piping bag with a star tip, don’t sweat it. Load up a zip-top bag and snip the corner. Or go old school and swirl a massive amount on with the back of a spoon. Just keep a stack of extra spoons on standby because, no matter how restrained you think you are, you’ll be licking them. Add the candied oranges and cherries when you’re ready to serve. Cheers!

Old Fashioned Cupcakes

  • Servings: One dozen
  • Difficulty: Average
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Whiskey, orange zest and cocktail cherries give these easy cupcakes a distinctive, 'old fashioned' flair, complete with orange bitters-accented buttercream and a cherry on top!


Ingredients

  • 1 1/2 cups all-purpose flour
  • 2 tsp. baking powder
  • 2 pinches kosher salt
  • 1/2 cup (1 stick) unsalted butter, softened
  • 1/2 cup sugar
  • 1/2 cup brown sugar
  • 2 eggs, room temperature
  • 1/4 cup Gentleman Jack Tennessee whiskey (or lower proof smooth bourbon)
  • 1 tsp. real vanilla extract
  • 1 Tbsp. Luxardo cocktail cherry syrup (see notes)
  • 1/4 cup whole milk, room temperature
  • 1 Tbsp. finely grated orange zest
  • 1 recipe orange bitters buttercream (below)
  • 4 candied orange slices, quartered (I found these at Trader Joe’s)
  • 12 cocktail cherries, blotted on paper towel

Notes: The cocktail cherry syrup I used is very thick, like pancake syrup. If using thin syrup, reduce amount of whiskey or milk.

Directions

  1. Preheat oven to 350° F, with oven rack in center position. Line 12-muffin tin with double cupcake papers.
  2. Combine flour, baking powder and salt in a medium bowl and whisk to combine. Set aside.
  3. In a stand mixer, or a bowl with hand mixer, cream butter until softened. Add brown and white sugars gradually, beating continually. Stop to scrape down bowl twice. Add eggs, beating after each. Stream in whiskey and cocktail cherry syrup. Scrape down bowl.
  4. Add 1/3 of the flour mixture and beat on low just until incorporated. Beat in half of the milk, then repeat with half of remaining flour, more milk, last of flour. Stop mixer and scrape down bowl, folding in the orange zest at the end.
  5. Divide batter into lined muffin cups. They will be roughly 3/4 full. Bake 18 to 22 minutes; cupcakes are finished when they pass the toothpick test.
  6. Cool in pan for about 15 minutes before transferring to a wire rack to cool completely.

Ingredients

  • 1/2 cup (1 stick) salted butter, softened at room temperature
  • 2 Tbsp. dulce de leche
  • About 4 cups confectioner’s sugar (depending on desired consistency)
  • 3 tbsp. Gentleman Jack
  • 2 tsp. Stirrings blood orange bitters (or 1 tsp. regular orange bitters)
  • Heavy cream, if needed to thin icing to desired consistency

Look for dulce de leche in the canned milk aisle, or use a sticky caramel topping as a substitute. You could also omit this if you don’t mind giving up the caramel accent.

Directions

  1. Using the whip attachment of a stand mixer, or whip beaters of a handheld mixer, cream the butter and dulce de leche until soft and fluffy.
  2. Add half of the confectioner’s sugar and beat until incorporated, then stream in whiskey and orange bitters. Add remaining sugar a few spoonfuls at a time until you achieve desired consistency. If you overdo it, whip in a tablespoon or more heavy cream.
  3. Pipe or spoon buttercream onto cupcakes, and garnish them with the candied orange slices and cocktail cherries.


Mint Julep Cupcakes

I have come to an important conclusion— that the only difference between me being a good baker or a bad one is my own level of commitment. How can anyone improve their skills without practice? Trial and error are an important part of the process, and I’ve seen plenty of that. Every once in a while, though, I land in the success column with both feet. Those are the good baking days!

These cupcakes are a beautiful addition to the Kentucky Derby table.

These cupcakes, which draw their inspiration from the Mint Julep, official cocktail of the Kentucky Derby, turned out so ridiculously good last year that my friend, Linda, practically demanded that I make them again this year. What makes these cupcakes so delicious— besides the obvious fact that, duh, they’re cupcakes— is that real Kentucky bourbon is added to both the cupcake batter and the icing. They are boozy, but not overly so. The sweet buttercream with accents of mint offsets any harshness that one might expect from the bourbon.


Kentucky Derby is an occasion that we enjoy for the theme as much (or more) than the horse race itself. It’s a rare event that gives me an excuse to wear a fancy hat, and I will try again this year to get my husband to put on a bow tie (we’ll see). My table will be filled with plenty of fancy finger foods, because it’s helpful to have one hand free to hold a mint julep or one of my other fun cocktails. When it comes to the mint julep cupcake— well, it’s another opportunity for me to have my cake— and drink it, too!

Did I sample two of the cupcakes before the party started? Maybe. 😉

Let’s Get Cooking!

If there’s one bit of advice I would offer for successful baking— to myself as well as anyone else— it would be to plan ahead, measure everything out and line things up before starting a recipe. Having my ingredients at the proper temperature is important as well, both for easy mixing and having a reliable baking time. For these cupcakes, the butter and eggs should be near room temperature, and the flour should be measured following the fluff, sprinkle, level method. Measure out the bourbon, too, so that you aren’t trying to guess the amount straight from the bottle. I used my cocktail measuring cup, which worked perfectly.

The cupcakes are definitely more substantial than a box mix cupcake, which makes a great base for piling on the sweet, minty buttercream. The batter includes both cane and brown sugar, which emphasizes those warm, caramel-like notes in the bourbon. I followed a typical method of creaming together the butter and sugar, then adding eggs and bourbon (in place of vanilla), and finally alternating additions of the flour mixture and milk. They baked up beautifully, and I cooled them completely before icing them.


This was my first time making buttercream, and I’m not sure if it was beginners luck or what, but it turned out so much better than I expected. I used salted butter rather than unsalted, because a touch of salt emphasizes whatever other flavors are around it, including sweet ones. I mixed in the powdered sugar, one cup at a time, and drizzled in the bourbon and mint extract somewhere in between the sugar additions. A little bit of heavy cream helped me achieve the right consistency, so that the icing would still have enough structure to hold its shape when piped onto the cupcakes.


Silver foil liners, a pinch of green sanding sugar and fresh mint sprigs put the perfect finishing touches on these delightful Kentucky Derby treats.


Mint Julep Cupcakes

  • Servings: 1 dozen cupcakes
  • Difficulty: Average
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These pretty cupcakes have bourbon in both the batter and the minty buttercream icing, making them a perfect finish to any Kentucky Derby party.


For the cupcakes, begin by measuring the flour by the fluff, sprinkle, level method. If you dunk a scoop directly into the flour, your batter will be too dense. Butter, eggs and milk should be near room temperature for best results.

Ingredients

  • 1-1/2 cups all-purpose flour
  • 2 tsp. baking powder
  • 2 pinches kosher salt
  • 1/2 cup (1 stick) salted butter, softened
  • 1/2 cup sugar
  • 1/2 cup brown sugar
  • 2 eggs, room temperature
  • 1/4 cup bottled-in-bond bourbon
  • 1/3 cup whole milk, room temperature

Directions

  1. Preheat oven to 350° F, with oven rack in center position. Line a standard cupcake tin with paper liners inside foil liners.
  2. In a medium bowl, whisk together flour, baking powder and salt.
  3. Using a stand mixer (with beater blade attachment) or electric hand mixer, cream together the butter and sugars until fully blended and somewhat fluffy.
  4. Add eggs, one at a time, beating well after each addition. Stream in bourbon and beat until fully blended.
  5. Add flour mixture, a little at a time, alternating with the milk. Beat after each addition, but only until blended.
  6. Divide batter among prepared cups; each cup will be approximately 3/4 full. Bake for about 18 minutes, until cupcakes are golden and a toothpick inserted into the center of a cake comes out clean. Cool in the cupcake pan for 15 minutes before transferring to a wire rack to cool completely.

For the buttercream icing, you’ll want the butter softened to near room temperature. Make this while the cupcakes are baking, then refrigerate the icing in a piping bag until the cupcakes are completely cooled.

Ingredients

  • 1/2 cup (1 stick) butter, softened to room temperature
  • 4 to 4-1/2 cups confectioner’s sugar (depending on your sweet tooth)
  • 2 tbsp. Bottled-in-bond bourbon
  • 1 tsp. pure mint extract
  • Up to 1/4 cup heavy cream, as needed to loosen the frosting
  • Fresh mint leaves and green sanding sugar, for garnishing

Directions

  1. Using a stand mixer (fitted with whisk) or an electric hand mixer, beat butter until smooth and creamy. Add confectioner’s sugar, one cup at a time, beating until smooth after each addition. Drizzle in bourbon before the final addition of sugar.
  2. Beat in mint extract and enough heavy cream to loosen the icing to desired consistency. Transfer icing to a piping bag and refrigerate until shortly before you will be ready to serve the cupcakes. Pipe onto cupcakes with a flower tip. Sprinkle each with a pinch of green sanding sugar (if desired) and garnish each cupcake with a sprig of fresh mint.



S’mores Cupcakes

My cousin, Annie, has a wicked sense of humor. Wicked, meaning funny, but also just a little bit wicked. During my visit last month at her lake house in Connecticut, Annie caught me off guard with what seemed like would be important, somber information.

“OK, listen” she began, cracking open a tall pantry door next to the kitchen of her sweet, cozy cottage. “If something happens to me, and you guys have to come here to the lake after I’m gone…”

“Yes,” I said, swallowing hard at that awful thought, as she pointed to a lower shelf inside the cabinet.

“Here’s where you’ll find the stuff for s’mores.”

Honest to God, I don’t know how she keeps a straight face when she delivers a punchline like that. But one thing is for sure, if there is an opportunity to bring joy to any situation or gathering, she has it covered— including s’mores, which we enjoyed as we relaxed in front of her patio fireplace, with the backdrop of gentle lapping sounds of the lake and an occasional bullfrog bellowing somewhere off in the distant darkness.


Who doesn’t have fun s’mores memories? The sweet little campfire sandwich of graham crackers, chocolate bar and toasted marshmallow has been a favorite of mine since I was a kid, and I was thrilled a few years ago to learn that the sugary treat has been awarded its very own day of celebration— National S’mores Day! Each August 10th since I started Comfort du Jour, I have presented a fun interpretation of s’mores. In 2020, it was a duo of treats with a s’mores cocktail and dessert pizza. In 2021, I gave you s’mores ice cream. Last year, those ooey-gooey s’mores brownies. And this year, well, it isn’t really a surprise, is it?

Behold, s’mores cupcakes!

These turned out to be everything I wanted!

With a sweet honey-graham cake base, hollowed out for a dark-and-milk chocolate ganache filling, and topped with a homemade marshmallow frosting (toasted, of course), this may be my favorite s’mores treat to date. 


I’d been scouting out component recipes for these for several months, and finally nailed it down after flipping through a special edition Food Network Magazine, called “The Cupcake Cookbook.” The pages held all kinds of cupcake creations, from fruit to spice to chocolate and vanilla, plus numerous flavors and types of frosting, icing and glaze. It was their recipe for “honey-graham cupcakes” that sealed the deal for my s’mores recipe, but I did (of course) put my own spin on them, using honey in place of sugar for an extra-sweet, extra-“graham-y” impression. 

I had this cocoa-infused honey that I had picked up on an earlier trip to Asheville, N.C., where we go occasionally to visit my husband’s adult daughter. I suspected that the cocoa infusion would lend itself nicely to the s’mores vibe, and I was correct. The honey has been in my cabinet for about a year, so it was fairly crystallized, but the texture was no problem for my baked recipe.


One of the things that appealed to me about the Food Network cupcake recipe is that it included actual crushed graham crackers. I was guaranteed to have the flavor I wanted, along with a slightly grainy feel from the already baked crumbs mixed into the cupcake batter. To crush the graham crackers, I piled a couple sleeves of them into my bullet-style blender and pulsed them for about 20 seconds, until they were reduced to a fine powder. I had the 3/4 cup of crumbs that I needed, plus 1/4 cup left over that I figured I’d use in the topping.


With all my ingredients lined up and measured, I was finally ready to bake!

Generally speaking, you can swap honey for sugar in a baking recipe, but you must take a few things into consideration, which I learned thanks to this article from an online honey supplier. Following those tips, I made the following adjustments:

  • used less honey than the sugar amount called for (because honey is sweeter)
  • reduced the milk amount slightly (because honey is also somewhat liquid)
  • added a touch of baking soda to balance the acidic effect of the honey
  • reduced the baking temperature a bit (because honey burns more easily than sugar), and slightly increased the baking time to compensate

I have accounted for all of those adjustments in my instructions, but the click-to-print recipe below also describes how the recipe should look if you’re using sugar to sweeten the cupcakes.


The ganache filling was the simplest component of this recipe; nearly equal parts chocolate— I used a combination of dark and milk chocolate for this— and heavy cream heated to just-shy of boiling. If you’ve never made ganache, you might be surprised how simple it is. Just heat the cream, pour it over the chocolate so it’s complete covered, wait 10 minutes, and stir to blend. Don’t be alarmed if the mixture seems very runny at first— it will thicken and firm up a bit as it cools. I wanted the ganache to be soft but not too messy, so I used slightly more chocolate than cream. In hindsight, equal parts would have been fine.


When the cupcakes were cooled, I used my apple corer tool to carefully cut out a plug shape bit of cake, keeping those pieces intact, to place back on top of the ganache, which I spooned inside the cupcake cavity. I didn’t mind that the tops didn’t sit flush with the cakes, because the whole thing would soon be buried in marshmallow frosting anyway. I had some ganache left over after filling the cupcakes, so I warmed it over hot water back to a spreadable consistency, and glazed the top of each cupcake, and then sifted some of the remaining graham crumbs on top as a bed for the marshmallow frosting.


Almost done! I agonized a bit over which frosting recipe to use, and considered one in the Food Network Cupcake magazine, but it sounded more like meringue than frosting, and I wanted mine to be stable enough to keep its shape without getting watery. I finally found a “marshmallow frosting” recipe online that sounded more hefty, and about the time I got to the step to “whip it with a mixer for seven minutes over simmering water,” it occurred to me that this was exactly the same as a topping that my grandmother frequently made during her having-company-over days.


Turns out, seven-minute frosting is essentially marshmallow creme. I suppose you could probably just top the cupcakes with store-bought marshmallow creme, but by this time, my frosting was already done and I did enjoy piping the stuff onto the cupcakes— it made me feel like a real baker!

The only thing left to do was was toast the marshmallow topping. Having never done this before, and not wanting to ruin my pretty little s’mores cupcakes, I piped out some of the leftover marshmallow frosting onto a sheet of foil, and hit the dollops with my culinary torch to practice. Would you believe, this turned out to be the simplest part of the recipe?! The frosting toasted beautifully, and it stayed pretty for a few days after I made the cupcakes. 


Incidentally, I had enough marshmallow frosting left over to cover at least two more batches of cupcakes, and most of the extra went to waste because I didn’t have a plan ready for using it. Perhaps I could have whipped up a quick batch of Krispie treats— and that of course, gives me an idea for National S’mores Day next year. 😉


S'mores Cupcakes

  • Servings: 12
  • Difficulty: Intermediate
  • Print

With a sweet honey-graham cake base, hollowed out for a dark-and-milk chocolate ganache filling, and topped with a homemade marshmallow frosting (toasted, of course), this may be my favorite s’mores treat to date. There are three components of this treat, and I've described each separately below.


Ingredients

  • 3/4 cup honey graham crackers, crushed fine (see notes)
  • 3/4 cup all-purpose flour
  • 1 tsp. baking powder
  • 1/8 tsp. baking soda (omit if using sugar in place of honey)
  • 1/2 tsp. salt
  • 1 stick unsalted butter
  • 1/2 cup honey (or 1 cup granulated sugar)
  • 2 eggs
  • 2 tsp. real vanilla extract
  • 1/2 cup milk (minus 2 tablespoons if using honey)

Notes: Butter, eggs and milk should be at cool room temperature. Remove them from refrigerator about one hour before you plan to start the recipe.

To get a fine crush on the graham crackers, I broke them up into my bullet-style blender and processed them for about 15 seconds. Sift through them with your fingers to remove any remaining chunks. I used two wrapped packs of “Fresh Stacks” crackers, and had about 1/4 cup of crumbs left over, which I sprinkled on top of the ganache before frosting.


Directions

  1. Preheat oven to 330° F (or 350° F if using sugar), and line cupcake pan with foil liners.
  2. Combine crumbs, flour, baking powder, soda and salt in a medium bowl and set aside.
  3. In a stand mixer, cream butter on medium speed until light and airy, about one minute. Add honey and beat on medium speed until fluffy and evenly blended, about four more minutes. Scrape down sides of the bowl.
  4. Add one egg at a time, beating to blend after each. Scrape down sides of the bowl. On low speed, beat in one-third of the flour mixture just until no visible dry ingredients remain. Beat in half of the milk. Repeat with dry ingredients, then milk, then final dry ingredients. Scrape down sides.
  5. Scoop cupcake batter into lined cupcake pan. Each cup should be about 2/3 filled.
  6. Bake 25 to 30 minutes (less if using sugar), until cupcakes are golden and spring back easily when touched in the center.
  7. Cool cupcakes in pan 5 minutes, then transfer to a wire rack to cool completely.

While the cupcakes are baking, prepare the ganache filling. It’s best to fill the cupcakes while the ganache is still somewhat warm and easily drizzled.

Ingredients

  • 2/3 cup quality chocolate, wafers or bars preferred over chips
  • 1/2 cup heavy cream

Directions

  1. Add chocolate pieces to a medium bowl. Heat cream to just-shy of boiling point. Pour cream over chocolate and let sit 10 minutes.
  2. Gently whisk or stir cream and chocolate together until evenly blended. This will seem impossible at first, but within one minute, it should be glossy and silky.
  3. When cupcakes are completely cool, used an apple corer tool or paring knife to carefully cut a one-inch plug from the center of each cupcake. Set these aside.
  4. Use a spoon to drizzle the warm ganache into each cupcake hole, then press the plugs back onto the cupcake. Carefully glaze the filled cupcakes with any remaining ganache. Scatter some of the remaining graham crumbs over the top and cool completely while you make the marshmallow frosting.

To prepare the frosting, you will need an electric hand mixer and a double boiler or a large, heatproof bowl that will fit over, but not inside, a medium saucepan. Be sure the mixing bowl and beater blades are completely clean, as any amount of oil or fat on them will prevent the egg whites from forming peaks.

Ingredients

  • 2 egg whites, at room temperature
  • 1 1/2 cups granulated sugar (I used a 50/50 mix of cane sugar and superfine caster sugar)
  • 1/3 cup water
  • 1 Tbsp. light corn syrup (prevents crystallization)
  • 1/8 tsp. fine salt
  • 2 tsp. real vanilla extract

Directions

  1. Bring a medium saucepan of water to a slight boil over medium heat. The water should not be high enough to touch the bottom of the bowl used in the next step.
  2. In the heatproof bowl, combine all ingredients except vanilla. Do not place the bowl over the hot water yet.
  3. Use a hand mixer to whip the frosting ingredients together. Start on low speed and increase slightly when the mixture starts to get frothy. After a minute or two, place the bowl over the simmering water.
  4. Continue to whip with the mixer for 7 minutes, until all the sugar has dissolved and soft peaks form in the frosting. Remove from heat.
  5. Add vanilla and beat again just until incorporated. Cool a few minutes before frosting cupcakes.
  6. Load frosting into a piping bag with a wide, round tip. Pipe frosting onto cupcakes.
  7. Use a culinary torch to carefully toast the marshmallow topping. Cool before enjoying.