Home » Cocktail Recipes » How to Make a Glorious Fall Rye Whiskey Cocktail

How to Make a Glorious Fall Rye Whiskey Cocktail

5 from 2 votes

This post may contain affiliate links. Read my disclosure policy.

Fall Rye Amaro cocktail with orange, cinnamon, star anise garnish
Fall Rye Amaro Cocktail – But I’m Not Bitter

With the cooler weather upon us we are officially in whiskey season, and what better way to celebrate than a fall rye whiskey cocktail. While I love whiskey year-round, fall and winter are the seasons more people gravitate towards whiskey. I suspect it’s that warm “Kentucky Hug” you get with a great finish on a glass of whiskey.

(Post may contain affiliate links)

Rye Whiskey in Fall Cocktails

Instead of reaching for bourbon for this cocktail, I wanted to play with the flavors of rye. Some ryes taste so like bourbon it’s hard to tell them apart except for the more rounded mouthfeel of the rye whiskey. Ryes with a 51% rye mash bill are particularly hard for me to identify in a blind tasting against a high rye bourbon whiskey. For this fall rye whiskey cocktail, I went with Wilderness Trail rye – one of my favorites.

Fall Rye Amaro cocktail with orange, cinnamon, star anise garnish
Fall Rye Amaro Cocktail – But I’m Not Bitter

Rye, to me is spicier, with a lovely peppery kick at the end of the finish. The mouthfeel coats the whole inside of the mouth – not just the back of the throat or sides. That full mouthfeel on a great rye is one reason I continue to expand my rye whiskey collection. Wilderness Trail uses a 56% rye, 33% corn, 11% malted barley mash bill for their spirit and keeps to a low barrel entry proof at 100 to 105 proof. The low barrel entry proof is one of the reasons it’s so good, even at just 4 years old.

On the nose this rye is sweet, peppery, with touch of grain. The higher malted barley content makes me think of a sweet Speyside Scotch, but the nose also has a good bit of oak and baking spices as well. As far as flavors, I get that lovely rye grain, spicy pepper, and a strong note of cinnamon as well as a dried fruit and citrus.

As a category of spirit, American straight rye whiskey, under many of the same restrictions as bourbon in the US, balances a sweetness from the mash bill with the spicier, peppery notes from the rye. By law, the mash bill must contain 51% rye, bottled at no lower than 80 proof, aged in new charred oak containers and go into the barrel at no more than 125 proof. Look familiar? It’s the same as bourbon, just with a different minimum grain.

Canadian ryes are so varied I am sure you can find an excellent fit here. Look for something with a good balance of spice and sweetness, but one that can blend well with more complex flavors we’ll be adding with the amaro.

Fall Whiskey Cocktails Need Amaro

Fall Rye Amaro cocktail with orange, cinnamon, star anise garnish
Fall Rye Amaro Cocktail – But I’m Not Bitter

If you’re not familiar with amaro, it’s a bitter liqueur with Italian roots. It’s made from a base of alcohol infused with different herbs, flowers, roots, barks, and spices. It’s a low alcohol spirit – from 15% to 40% alcohol by volume and it’s often imbibed on its own, over ice, or in a spritz.

There are hundreds of Amari (plural of amaro), each with its own secret and proprietary infusion methods and ingredients. Remember that while they are bitter, they are also sweet, and each Amaro is unique in its flavor and aromas.

For this fall rye whiskey cocktail I’m focused on Montenegro Amaro. It’s a sweet, floral, bitter liqueur with notes of licorice, cherry, and orange. It’s not as full of chocolate or coffee notes as many other Amari, so it’s a perfect match here to go with the peppery baking spices of the Wilderness Trail rye.

Chai Spice-Infused Simple Syrup

Fall Rye Amaro cocktail with orange, cinnamon, star anise garnish
Fall Rye Amaro Cocktail – But I’m Not Bitter

While Montenegro Amaro is sweet on itself, I needed a bridge between the rye’s baking spices and pepper and the floral, licorice flavors of Amaro. A chai spice-infused simple syrup was just what I needed.

For more information on making simple syrups and the recipe for this creation, go here. I reduced 2 cans of Regatta Craft Mixers’ ginger beer by half. Then I added chai spices like cinnamon, nutmeg, cardamom, peppercorn, anise, and allspice to the reduction while it cooked down. I added a little sugar to make it a bit thicker and had a perfect infusion on my hands.

The chai’s star anise, cinnamon and pepper tied the Montenegro directly to the Wilderness Trail. While you can make the fall rye whiskey cocktail without the syrup, the flavors marry in a way more complex and intriguing with it.

How to Make this a Batch Fall Rye Whiskey Cocktail

Because this fall rye whiskey cocktail has only three ingredients it’s an easy cocktail to batch. Simply convert each of the ounce measurements to cups and you’ll have 8 cocktails to sip on or share.

Combine ingredients in a quart mason jar or pitcher and stir. Keep refrigerated. Before serving, I put it in the freezer for 30-45 minutes for it to get cold.

Easy Garnish

One of the things I love about fall is the easy garnish – in this case a dried orange, cinnamon stick, and star anise. And if you’d like, you can light them on fire for more of a smoked vibe.

Recommended Bar Tools

You don’t need every slick, beautiful bar tool out there, but there are several I’ll recommend. (As an Amazon Associate I earn from qualifying purchases. However, that does not affect the cost of the items below.) My favorite pieces usually come from the Cocktail Kingdom section of Amazon:

You may already have these bar essentials, but just in case:

Fall Rye Amaro cocktail with orange, cinnamon, star anise garnish
Fall Rye Amaro Cocktail – But I’m Not Bitter

Fall Rye Whiskey Cocktail – But I’m Not Bitter

Picture of Heather Wibbels, Cocktail Contessa, pouring a cocktailHeather Wibbels
Get all the flavors of the season in this fall rye whiskey cocktail with rye, amaro and a chai simple syrup. The combination of a floral amaro with a peppery rye is married with the spices of the chai infusion, including cinnamon, nutmeg, ginger, peppercorn, allspice, and clove.
5 from 2 votes
Course Drinks
Cuisine rye cocktail
Servings 1


  • 1.5 oz Wilderness Trail Rye whiskey
  • 1 oz Montenegro Amaro
  • 1/2 oz chai spice-infused simple syrup from reduced Regatta Craft Mixers Ginger Beer
  • Garnish: dried orange slice cinnamon stick, star anise


  • Combine ingredients in a mixing glass and add ice. Stir until chilled and well-combined. Strain into a rocks glass with one large cube. Garnish with orange slice, cinnamon stick, and star anise.


Go to the end of the article on this page for the Chai Spice-Infused Simple Syup
Keyword amaro, cardamom, chai simple syrup, cinnamon, clove, nugmeg, star anise
Tried this recipe?Let us know how it was!
By on October 9th, 2020
Picture of Heather Wibbels, Cocktail Contessa, pouring a cocktail

About Heather Wibbels

Heather Wibbels is a whiskey and cocktail author (Executive Bourbon Steward, no less) with a passion for cocktails. She loves researching and designing cocktails, drinking cocktails, and teaching cocktails. Mostly whiskey cocktails, given her Kentucky location.

More posts by this author.

1 thought on “How to Make a Glorious Fall Rye Whiskey Cocktail”

  1. 5 stars
    This is a winner and will be included on our Thanksgiving menu. I used a different brand of Amaro and Whiskey but I made the chai simple syrup from the recipe on this site (which is worth the effort). My husband is partial to whisk(e)y cocktails and chai tea so of course he loves this combo. Thank you for this gem.

5 from 2 votes (1 rating without comment)

Leave a Comment

Recipe Rating