Chocolate-Covered Cherry Old Fashioned

The whole world seemed to be holding its breath this time last year, as health officials everywhere began sounding major alarms about the potential dangers of COVID-19. If I had known that Valentine’s Day would be one of the last opportunities for life as we knew it—well, I might have made an exception for my usual “let’s stay at home and celebrate” attitude.

Or maybe not. I’ve never quite appreciated the way the food service industry has dealt with Valentine’s Day—raising prices while simultaneously reducing menu options doesn’t seem terribly romantic, just opportunistic. I put this couple’s night out in the same category as New Year’s Eve. Why in the world would a restaurant place restrictions on a “special” occasion, as if they are not capable of handling a full house with their regular menu? It shouldn’t be much different from a typical busy Saturday night. I don’t get it.

Happily though, I love the anticipation of preparing a special dinner at home, and for Valentine’s Day, I pull out all the stops to make decadent dishes for the love of my life. ❤

I have mentioned previously that my husband, Les, is completely crazy over anything that combines chocolate and cherry, as with the triple chocolate-cherry brownie bowls I shared from his birthday last summer, and the entire Valentine’s meal I made for us last year, only a few weeks before I started Comfort du Jour. It was “all about the cherries” for that occasion, and I prepared duck breast with a cherry-pinot noir sauce (it’s what I was making in the “about me” photo in the section at the right, plus chocolate crepes filled with mascarpone and topped with cherry-chocolate sauce, and we began the evening with this candy-inspired cocktail—the Chocolate-Covered Cherry Old Fashioned. Les and I had made fast friends with the classic Old Fashioned, and I knew the cherry and chocolate would give it a perfect twist.

My Valentine’s favorite flavor combination, in a romantic cocktail!

During the holidays this year, we were introduced by his daughter to the most incredible chocolate covered cherries of all time, sold by Trader Joe’s. These sweet little nuggets pack a lot of decadence into one bite, including a rich dark chocolate jacket and a silky, boozy liqueur floating around a candied cherry. It is not unusual for us to choose these little gems for satisfying our post-dinner sweet tooth. We will be bummed when the box is empty, as we will have to wait until next holiday season to get more of them.

This riff on a classic rocks drink replicates the decadent experience of that limited-edition treat, combining the sweetness of cherry and the romance of Valentine’s chocolate with the spirit of bourbon. At our house, we love the accent of almond with cherry and chocolate, so there’s a little splash of amaretto in the cocktail as well. Whether you’re staying home to celebrate Valentine’s Day with a loved one, or simply to enjoy the pleasure of your own company (as you absolutely should), I hope you’ll enjoy this special sweetheart of a cocktail.


Ingredients

Makes one cocktail; simply double ingredients if making for two.

Find the chocolate bitters and cherries in a gourmet shop or online. The Luxardo cherries are, in my opinion, well worth the typical $20.

1.5 oz. bourbon (Elijah Craig Small Batch is on my bar right now)

0.5 oz. (1 Tbsp.) Godiva dark chocolate liqueur

0.5 oz. cherry juice (I used Trader Joe’s, but any brand is fine)

0.25 oz. (1 1/2 tsp.) amaretto

1 bar spoon (about 1/2 tsp.) syrup from Luxardo cocktail cherries* (see notes)

3 drops chocolate bitters*

To garnish:

Cocoa powder (for rimming the glass)

Premium cocktail cherry (such as Luxardo)


*Notes

For the love of cocktails, please put away the artificial maraschino cherries! The Luxardo cherries mentioned here are the Ferrari of all cocktail garnishes, produced in Italy using real Marasca cherries that are macerated in Luxardo maraschino liqueur and packed in the resulting syrup. They are pricey, but completely worth it, and a jar will last a long time. Find these in gourmet shops, the cocktail mixers section of a high-end supermarket or online.

My chocolate bitters are produced by Woodford Reserve (the bourbon maker) and they add depth, not bitterness, to a cocktail. Find them in the cocktail mixers section, perhaps at Total Wine or online.

Instructions

Prepare a double rocks cocktail glass by wetting the rim with a small amount of chocolate liqueur, holding the glass upside-down so that the liqueur doesn’t run down the sides. Then roll only the outside edge of the cocktail glass into a bit of the cocoa powder. This keeps the cocoa outside the drink, giving you an extra hint of chocolate on every sip. Do this a bit ahead of time so that the cocoa rim has time to dry and set up on the glass.


At cocktail time, combine bourbon, chocolate liqueur, amaretto, cherry juice, syrup and bitters in a cocktail mixing glass. Add a cup of ice and stir about 20 seconds to chill down the cocktail mixture. Strain into the cocoa-rimmed glass over a giant ice cube. Garnish with a good cocktail cherry (or take it home by skewering an actual cordial cherry).


If you really want to go crazy with the garnish, gently push your cocktail pick directly through a chocolate covered cherry. Pure decadence!

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Triple Chocolate Cherry Brownie Bowls

There’s dessert for the sake of a sweet tooth, and then there’s DESSERT, as is the case with this ultra-chocolate-y, cherry-infused brownie bowl, packed with “Cherry Garcia” vanilla ice cream, studded with sweet cherries and dark chocolate chunks. Oh, and I almost forgot, the cherry syrup. Over the top? Obviously! But this was a birthday dessert a few weeks ago for my husband, Les, who is himself a little “over the top” crazy about any and all chocolate and cherry combinations. And for such an occasion, during a year that has given us too much to worry about and not enough to celebrate, I went all in.

Well, almost. I did take one easy shortcut and I’m not ashamed to share my little secret with you—I never make brownies from scratch. I have a favorite box brownie mix that meets all my picky ingredient requirements, so why put forth the effort to make it “as good as” theirs, when they already have a product that is a winner every time? Ghirardelli dark chocolate is my go-to, and though the brownies are terrific as directed on the box, I sometimes can’t help but elevate them with my own “extras” to highlight certain aspects of the brownies’ personality. It’s easier than you might expect.

For these birthday brownie bowls, I’ve substituted cherry juice for the water called for on the package instructions, and I’ve added a tablespoon of dark cocoa powder plus a handful each of chocolate chunks and cut up dried cherries. That’s it. The simplest flavor swaps, resulting in the most decadent dessert my hubby could have ever asked for on his birthday (or any other occasion). Luckily, for our ever-expanding pandemic waistlines, it will be another year before we indulge to this degree. But it was kinda worth it. 🙂

Chocolate, cherries, more chocolate, brownie, cherry sauce. What could possibly go wrong?

These brownies are super-sized and shaped like a bowl, exactly right to hold a generous scoop of ice cream (which I did make from scratch, but don’t feel pressured to do so). The special shape is courtesy of a fancy-schmancy pan I bought from King Arthur Baking Company. At $30, it was a bit of a splurge, but in this most ridiculous year, I’ve been willing to invest a bit more in kitchen gadgets and ingredients to make our home meal experiences more memorable. Mark my word, it’ll pay for itself by the time the holidays get here, because I’m already dreaming up other ideas.

The pan has a no-fail nonstick coating. The brownie bowl holds a perfect scoop of ice cream.

If you’re not feeling the love for a special pan to make bowl-shaped brownies, don’t stress about it. Make the brownies in a regular pan according to the mix instructions. You can still swap in the special flavor ingredients and have a spectacular dessert with minimal effort. Remember, stressed spelled backward = desserts, and I’m all about flipping things around! 🙂


Ingredients & Instructions

1 box of your favorite brownie mix (make according to package instructions, but adjust as noted below)

Substitute equal amount of cherry juice for the suggested amount of water

Add 1 Tbsp. dark cocoa powder to the dry mix (Hershey’s special dark will do, and it’s easy to find)

Add 1/2 cup dried dark cherries, cut into smaller pieces (fold in after mixing)

Add 1/2 cup dark chocolate chunks or semi-sweet chocolate chips (fold in after mixing)

Bake as directed on the package, but if you use the King Arthur brownie bowl pan, you’ll want to cut the time in half. My brownies were perfect after 25 minutes.

Fill ‘em up!

Cherry Garcia ice cream from Ben & Jerry’s (or whatever other ice cream rocks your world)

I made my own version of “cherry Garcia,” but we usually purchase the Ben & Jerry’s brand, which is great!

Top ‘em off!

Hot fudge topping, whipped cream, or (if you’re feeling inspired) my quick homemade cherry sauce.

Cherry on top of cherries! This sauce is easy to make and also happens to be excellent on crepes or any kind of ice cream.

Cherry Sauce*:

2 cup frozen dark sweet cherries

2 Tbsp. sugar

1 tsp. pure vanilla or almond extract (or 1 Tbsp. amaretto liqueur or chocolate liqueur)

1 Tbsp. dark chocolate balsamic vinegar* (optional)

2 Tbsp. corn starch, mixed with 2 Tbsp. ice cold water

Heat a small saucepan over medium heat. Add frozen cherries and sprinkle sugar over the top. Stir and cook until cherries are softened and mixture is reduced and bubbly (about 15 minutes). Add extract or liqueur and stir. Blend corn starch and water until smooth, and slowly drizzle into the cherry sauce, stirring constantly. Allow mixture to come back up to full simmer, and continue to stir as it thickens further. Remove from heat. Use the sauce warm over dessert or keep in refrigerator up to two weeks.

*This time around, I strained the cherries from the sauce because they went into the ice cream. Half of the sauce was drizzled through the ice cream like a ribbon, and the rest was reserved for spooning over the brownie bowls. It was a delicious labor of love!

This one’s for you, my birthday boy! ❤

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Cherry Amaretto Upside-down Skillet Cake

A great meal deserves a sweet, delicious ending, and this one showcases the plump and luscious dark red cherries that were everywhere this summer. The cake is moist and flavorful, rich with buttermilk, almond flour, eggs and real butter, and the buttery brown sugar topping is a little on the boozy side, plus the deep, dark sweet cherries. And the whole thing is elegantly draped with a dollop of amaretto-spiked whipped cream.

YUM!

If you aren’t wild about cherries (or maybe you aren’t wild about knocking out the pits), substitute fresh peaches, plums, nectarines, blackberries—well, I think you get the idea. But these cherries!

Fresh and sweet dark cherries

To tackle the unenviable job of pitting the cherries, I purchased a nifty device that gets the job done, six cherries at a time! If you’ve ever tried pitting cherries without a tool, you know that it cannot be done without making a huge mess. In previous attempts, I’ve balanced the cherries—one at a time, of course—on the neck of an empty wine bottle, then held the cherry while shoving the end of a chopstick through it. It left holes in the cherries, the pits inside the bottle, and red juice stains all over everything else in the room, including me. It’s the reason that, for the most part, I’ve relied on frozen cherries whenever I wanted to make a cherry dessert. I adore fresh cherries, but I’d only bought them to snack on, and only when I was flying solo because the whole spitting-out-the-pits part conjured memories of the 1987 film The Witches of Eastwick. There’s just no way to do it gracefully.

Suffice to say, this $15 tool has changed the game for me. After rinsing the cherries and pulling off the stems, I loaded them into the tray and pressed the top down. Boom!

And just like that, the pits are pushed out the bottom and into a receptacle, leaving the cherries intact but devoid of pits. I finished the entire bowlful in about 8 minutes. I’m not prone to give kudos for “uni-task” tools, but this one really took the pain out of what would otherwise make me choose a different dessert. Besides, as I reminded my husband, Les, this will also come in handy when I need to pit whole olives (which I’ve never tried but now I can).

After the cherries were pitted, I got busy making the topping, which goes into the skillet first. This part of the recipe felt familiar because I’ve made a similar upside-down skillet cake with peaches. I start by melting butter with brown sugar, then adding amaretto to the mix for a subtle almond flavor that echoes what will be going on later in the cake batter. The cake is easy to make, too—cream together the sugar and butter, add the eggs and flavor enhancers, and then alternate the dry ingredients with buttermilk until it’s ready to spread over the topping. The rest of the delicious magic happens in the oven.

It’s best to invert the cake onto a plate while it’s still warm, but be careful handling the hot skillet!

This cake has a dense, but not heavy texture, and the warm almond flavor permeates every layer while the soft, juicy cherries satisfy the sweet tooth. It keeps well, too, which is always a bonus in our empty nest household. As odd as it may sound, Les and I found that we enjoyed this cake even more a couple days after I baked it—ice-cold, straight from the refrigerator. The cake part remained moist (thank you, buttermilk!), and the cherry flavor was more pronounced.

Leftovers. The cake remained moist in the fridge, and the deep cherry color seeped further into the cake. This is a delicious dessert for late summer!

Ready to make it?


Ingredients

4 Tbsp. butter

1/2 cup brown sugar

1/4 cup cane sugar

1.5 oz. amaretto* (see notes)

About 3 cups pitted fresh dark cherries

1 cup all-purpose flour*

3/4 cup almond flour

1 tsp. baking powder

1/2 tsp. baking soda

1/2 tsp. salt

1/2 tsp. ground cinnamon

3/4 cup cane sugar

1 stick unsalted butter, softened but not melted

2 large eggs

1 tsp. vanilla extract

1 tsp. almond extract

1 Tbsp. amaretto (optional)*

1 cup buttermilk*

Whipped cream for serving, if desired


*Notes

Amaretto is an Italian, almond-based liqueur. It is lower proof than whiskey or vodka, slightly sweet and plays very nicely with cherries. If you avoid alcohol, you can get close to this flavor with almond extract. Drizzle 1 teaspoon over the cherry mixture and increase to 2 teaspoons in the cake. Real almond extract, by the way, also usually contains alcohol as a suspension for the almond flavor, but the amount will be minimal.

Remember the rule for measuring flour? In baked goods such as this, using the correct amount will really make a difference. Dipping your measuring cup straight into the flour container is a sure-fire way to have a dry and crumbly cake. I trust a kitchen scale for most of my baking, but if you don’t have one, follow the simple “fluff, sprinkle, level” method—fluff the flour with a whisk or fork, sprinkle it over the dry measuring cup to overflowing, level it off with the back of a knife.

Don’t be tempted to substitute regular milk for the buttermilk in this recipe. The acidity in the buttermilk will lend a subtle tanginess to the cake, and it also reacts with the baking powder and soda for leavening.


Instructions

  1. Preheat oven to 375°.
  2. Place a 10” cast iron skillet over medium heat. Melt the butter, then add the brown sugar and cook until the sugar is dissolved, and the mixture appears lightly foamy.
  3. Pour in the amaretto and swirl gently to evenly distribute throughout the butter and sugar mixture. Remove from heat and arrange the cherries close together over the mixture.
  4. In a medium bowl, whisk together flour, almond flour, baking powder, soda, salt and cinnamon.
  5. In a mixing bowl, beat together the butter and sugar until it’s evenly combined and fluffy. Add one egg and beat until smooth, repeat with the second egg. Then, beat in vanilla and almond extracts, plus additional amaretto, if desired.
  6. Beat in 1/3 of the flour mixture, blending only until dry ingredients are thoroughly incorporated. Beat in half the buttermilk until smooth. Repeat with flour and buttermilk, then the remaining flour.
  7. Pour the batter evenly over the cherries in the skillet. Smooth the top with a rubber spatula to evenly distribute the thick batter.
  8. Slide the skillet into the oven and bake about 50 minutes, or until a toothpick comes out clean.
  9. Allow cake to cool at least 15 minutes before inverting it to a large serving platter. To do this successfully, first slide a butter knife around the edges of the cake, to loosen any areas where it might be sticking. Center the plate, face-side down, over the skillet, then carefully hold the skillet and plate together and turn them over. I’ve found this to be easy, as long as you don’t allow the cake to cool too long. If it sticks too much to release, turn the pan right side up again and briefly heat it over a low burner. This will melt and soften the butter again for easier release.

Allow the cake to cool completely. Cut into wedges and serve with a dollop of freshly whipped cream (spike with amaretto, if you wish).

Store leftovers in the fridge, covered with foil or plastic wrap.

This recipe makes about 8 servings, and a dollop of fresh whipped cream is a perfect topper.

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