Sleepy Hollow
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I’m calling this the signature cocktail of the town of Sleepy Hollow. This Pomegranate Bourbon Sour is essentially what we’re serving to keep the Headless Horseman happy, and let me tell you, the flavors are everything you need and more for a Halloween Cocktail.
Watch Me Make It
How to Make a Sleepy Hollow
- Add bourbon, amaro, pomegranate juice, lemon juice, syrup, and bitters to a cocktail shaker with ice and shake.
- Double strain into a chilled glass.
- Garnish with a smoked sage leaf.
How to Make Blackberry Sage Cinnamon Syrup
Making this flavored homemade simple syrup is so easy and so worth it! You can use it in tons of other fall cocktails or drizzle it on pancakes, yogurt, ice cream, and oatmeal.
Add 1 cup water + 1 cup granulated (or brown) sugar + 1 cup blackberries + 6-8 sage leaves + 1 cinnamon stick to a medium saucepan over medium heat, stir until the sugar dissolves, and let simmer for 8-10 minutes. Remove from heat and let it cool completely. Once cooled, strain through a fine mesh sieve, making sure to really press all the liquid out. Store in the fridge for up to 4 weeks. Keep the blackberries left over in the strainer as a sort of jam for ice cream and breakfast treats!
You can also use this exact syrup in my Black Widow Smash cocktail!

Sleepy Hollow Ingredients
Bourbon
Bourbon is a type of whiskey that’s only made in the US. It has slightly sweet vanilla, caramel, oaky notes. Any kind of whiskey works in this recipe. Check out my Whiskey collection recommendations!
Amaro Nonino
Amaro Nonino is a bitter Italian herbal liqueur made from aged grappa (brandy distilled from fermented grape residue) and a wintery blend of herbs, spices, and roots. Nonino has a sort of allspice and orange peel flavor, making it the perfect holiday addition to the liquor cabinet.
Pomegranate and Lemon Juices
You can buy unsweetened pomegranate juice, but I recommend juicing your lemons fresh!
Angostura Bitters
A concentrated flavoring of herbs and botanicals, mostly used for cocktails. You could use orange or lemon bitters as well.

Tips for Making a Sleepy Hollow
- Make sure to get 100% pomegranate juice, not blends with other fruits or juices that have added sugar.
- Making your own flavored simple syrup really is the way to go here. It’s really easy and you can use the extra syrup in other cocktails and on ice cream, oatmeal, yogurt, pancakes, etc.
- Shake the ingredients in a cocktail shaker until the outside gets nice and frosty. You want all the ingredients to get really cold.
- Smoke your cocktail glass before adding the ingredients. Smoke a sage leaf and cover with the overturned glass and set aside while making the cocktail.


Sleep Hollow
Ingredients
- 1.5 oz bourbon
- 3/4 oz amaro Nonino
- 3/4 oz pomegranate juice
- 3/4 oz lemon juice
- 1/2 oz
blackberry sage cinnamon syrup - 2 dashes angostura bitters
Instructions
- Add all ingredients to a cocktail shaker with ice and shake.
- Double strain into your chilled glass.
- Garnish with a smoking sage leaf.






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