Chocolate Covered Cherry Amaro Manhattan Cocktail

July 5, 2022

Get out your rye whiskey, because we’re making Manhattans! A take on the classy cocktail, this amaro Manhattan features Averna, chocolate liqueur, cherry bitters and a homemade sour cherry shrub for that chocolate-covered cherry flavor.

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A Manhattan is one of those cocktails that makes you feel extra sophisticated and fancy no matter what you’re doing. And this version is like that feeling turned up a few notches. It’s made with amaro and chocolate liqueur, instead of vermouth, for a rich backdrop. But the star here is the homemade sour cherry shrub.

Shrubs are essentially a flavored fruit syrup made with vinegar. This one highlights seasonal sour cherries, which are then accentuated in the cocktail with a dash of cherry bitters and a few fresh skewered cherries to top it all off. This drink could literally be the cherry on top of any celebration, happy hour, or simple evening at home.

What You Need to Get Started

You can easily find all of the ingredients for this chocolate-covered cherry amaro Manhattan at your local stores:

How to Make a Cherry Cocktail Shrub

This entire cocktail was built around this shrub, which features one of my favorite types of fresh produce: sour cherries! If you are able to get these cherries right off the tree or from a local farm, I recommend it.

This recipe works best with fresh sour cherries, but if you are only able to access sweet cherries, use Rainier or white cherries, or any variety that leans a little bit more tart. Black cherries really don’t work well here, because they are just too sweet.

If you absolutely need to, you can use frozen sour cherries. However, be sure to allow them to thaw before making the shrub. Also, since they will likely not include any pits, you’ll want to increase the amount of cherries when measuring.

If you have a cherry pitter, go ahead and use it to remove the pits from your fresh cherries before getting started. But don’t toss them away! We’ll be using the pits a little bit later, since they are covered in plenty of good cherry flesh and juice.

If you don’t have a pitter, that’s fine too. You can always use a paring knife to remove the pits, or simply halve the cherries and get the pits out that way.

To begin making the shrub, combine the pitted cherries, sugar, and water in a small saucepan. Stir these together while cooking over medium-high heat. You want to allow the sugar to dissolve into the liquid, and bring the temperature up to a simmer.

Continue cooking at a simmer for five minutes or more. The mixture should be bubbling just a little bit, but not at a full boil. The idea here is to soften the cherries while cooking off some of the water, but not to remove all the liquid.

As the cherries begin to get softer, use a spatula or wooden spoon to squish them on the bottom and sides of the pan. Cook this until the mixture has thickened and the cherries have all been mashed.

At this point, turn off the heat.

Add in the vinegar and cherry pits to the saucepan with the mashed cherries, and stir to combine everything together. A shrub can be made with any type of vinegar, but I decided to use apple cider vinegar here for it’s fruitiness, which complements the cherries well.

It may seem counterintuitive to add acidic vinegar to the already-tart sour cherries, but it works well here. The vinegar actually helps counter the somewhat medicinal flavor cherry can sometimes have, and it keeps the full cocktail from being too syrupy.

Once it’s all stirred together, cover the pan loosely, such as with a piece of aluminum foil just resting on the top, and set it aside. We want to allow the flavors of the cherries and cherry pits to infuse into the liquid, and it also will cool down slightly.

When it’s ready, carefully pour the cooled shrub through a fine-mesh strainer into a mason jar or other container. Be sure to use a flexible spatula to press the cherry pulp, extracting any stubborn juices.

Cover this jar loosely until it has cooled to room temperature before storing. You can use the shrub warm if you are making the cocktail right away. If you are more of an advance planner, you can make this shrub and store it in a sealed jar in the fridge for a few weeks.

Let’s Make a Chocolate Cherry Amaro Manhattan

Now that we’ve got the shrub all prepared, it’s time to add the alcohol! A traditional Manhattan cocktail is made with rye whiskey, vermouth, and bitters. We’re straying slightly from that basic recipe, but keeping the concept and the appearance of the finished product pretty close.

Before you begin, fill your martini glass with ice water and set it aside to chill.

You’ll be mixing this cocktail in a mixer glass. If you don’t have one as part of a cocktail shaker set, any heavy-bottomed, tall glass that is wider at the top than bottom will work well. A standard beer pint glass is a great choice. Fill this about halfway with ice, and then begin adding your ingredients.

Start with rye whiskey. I suggest using your favorite craft variety from a local distillery if possible. If you’re new to rye whiskeys, a good one to start with is Sazerac Rye. You could also do a small whiskey tasting to try a few first, and then select a new go-to.

Next, add the amaro. The Averna I used here is meant to replace the vermouth in a traditional Manhattan. Amaros are an Italian herbal liqueur, and they come in quite a range of flavor profiles. For this cocktail, it’s best to stick with a sweeter one with hints of chocolate, like the Averna or Montenegro.

Now, add in the dark chocolate liqueur. I prefer Godiva, but if you have another preference, that will be delicious here as well. The important part is that it’s a dark chocolate or dark creme de cacao that doesn’t include any dairy.

Finally, add in the shrub that you prepared earlier. The cherry flavors from this will work well with the sweet chocolate of the liqueurs and the slight bite that you get from using rye whiskey.

Use a bar spoon to stir until everything is combined. Bar spoons are long handled with a fairly small bowl, and sometimes include a swirled handle to help with stirring. If you don’t have one, any long-handled spoon (like an ice cream sundae spoon) or even a butter knife will work in a pinch.

Now comes the tricky part, straining this into a martini glass. First, dump out the ice water you were using to chill your glass. Don’t worry about it being completely dry, a few water drops are fine here.

Place the cocktail strainer on top of your shaker glass, and secure it in place. Then pour from the mixer glass into your martini glass.

If you don’t have a specific cocktail type of strainer, that’s okay. You can pour the cocktail through a mesh strainer or even a small colander. The idea here is to leave behind the ice, and only get the liquid into the glass.

Add a few dashes of cherry bitters if you’d like to accentuate the cherry flavor even more. For something a little bit different, try this cocktail with a splash of cherry liqueur instead, or a dash of chocolate bitters.

Finally, let’s add a little garnish to this amaro Manhattan. I placed two extra sour cherries on a cocktail skewer. You can also use cocktail cherries or maraschinos, which can be skewered, or just dropped into the bottom of the glass. A little bit of orange peel on the rim is also a traditional garnish.

This finished cocktail is best made just before you want to serve it. However, since it is strained, you could store one mixed in the fridge for a day or so if needed. Also, it’s fairly easy to multiply the ingredients and mix up a larger batch for a big gathering.

Classy or casual, this chocolate-covered cherry amaro Manhattan is your new favorite cocktail to sip, no matter the occasion!

How to Serve a Chocolate Cherry Amaro Manhattan

Like the city it’s named for, the Manhattan can be dressed up or down. You could sip this cocktail at a white-tie event in a floor-length black gown or while curled up on the couch in sweats. Either way, you’d be enjoying it correctly. And since this version has a perfectly balanced sweetness, it can take you from brunch through happy hour all the way to a nightcap.

Naturally, serving this drink with dishes that also feature cherries and chocolate is sure to create a great pairing. Try it alongside some espresso chocolate chip muffins in the morning, or with cherry cheesecake napoleons for dessert. Or use both flavors in super moist cherry chocolate zucchini bread.

For something more casual like a happy hour or dessert spread, this amaro Manhattan is sure to pair excellently with cherry chocolate chip cookies, rocky road black bean brownies, or the light and refreshing lemon curd sandwich cookies.

More Whiskey-Based Cocktails

Chocolate Covered Cherry Amaro Manhattan Cocktail

A strong cocktail, made with rye whiskey, Averna amaro, dark chocolate liqueur, and a homemade cherry shrub for a chocolate-covered cherry with a kick!
Prep Time10 mins
Cook Time10 mins
Infusing Time45 mins
Total Time1 hr 5 mins
Course: Drinks
Cuisine: American
Servings: 1 drink
Calories: 234kcal

Ingredients

Sour Cherry Shrub

  • 1 Cup Fresh Sour Cherries whole, with pits
  • ½ Cup Sugar
  • ½ Cup Water
  • ½ Cup Apple Cider Vinegar

Chocolate-Covered Cherry Manhattan

  • 1 ½ oz Rye Whiskey
  • ½ oz Averna Amaro or similar
  • ½ oz Godiva Dark Chocolate Liqueur
  • ½ oz Sour Cherry Shrub
  • 1-2 dashes Cherry Bitters optional
  • 2 Cherries optional, for garnish

Instructions

Sour Cherry Shrub

  • Use a cherry pitter or paring knife to remove the pits from the cherries, and set the pits aside. Do not discard.
  • In a small saucepan, stir together the pitted cherries, sugar, and water until combined, and bring to a simmer over medium-high heat.
  • Continue to simmer for 5-8 minutes, squishing the cherries on the bottom and sides of the pan, until the mixture has thickened and the cherries have all been mashed. Then turn off the heat.
  • Add the vinegar and cherry pits into the pan, and stir to combine. Cover loosely, and allow the mixture to infuse and cool for 45 minutes.
  • Pour the cooled shrub through a fine-mesh strainer, using a flexible spatula to extract any excess juices, into a 16-oz jar. Cover loosely until cooled to room temperature.

Chocolate-Covered Cherry Manhattan

  • Fill a mixer glass about halfway with ice, and add in the rye, amaro, chocolate liqueur, and shrub. Use a bar spoon to stir until combined.
  • Pour through a cocktail strainer into a chilled martini glass, and top with cherry bitters if desired. Garnish with two skewered cherries and serve.

Notes

  • Make Ahead Tips:
    • The shrub can be made in advance and stored in a sealed jar in the fridge for 3-4 weeks. 
    • The cocktail itself is best made to serve. However, since it is strained, you could store one mixed in the fridge for a day or so if needed. 
  • Ingredients:
    • This works best with fresh sour cherries, but if you are only able to access sweet cherries, use Rainier or white cherries, or any more tart variety. Black cherries don't work well here, as they are too sweet. Frozen sour cherries should be thawed before using, and they will not have pits to add. Instead, increase the amount of cherries to 1 1/2 cups.
    • Rye is the traditional whiskey used in a Manhattan, and I suggest using your favorite craft variety from a local distillery if possible. If you're a beginner, try Sazerac Rye
    • The Averna amaro here is meant to replace the vermouth in a traditional Manhattan. I specify the brand because amaros come in quite a range. Stick with a sweeter one, with hints of chocolate, like the Averna or Montenegro
    • Cherry bitters are optional here, but add an extra hint of that sour cherry flavor. For something different, try this cocktail with a splash of cherry liqueur instead or a dash of chocolate bitters.
  • Non-alcoholic: For a zero-proof version of the shrub, combine it with seltzer or your favorite lemon-lime soda. A Manhattan can be difficult to recreate without alcohol, but you can come somewhat close using an alcohol-free whiskey, chocolate syrup, and cherry bitters.
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