# 11 Fall Whiskey Cocktails And Old Fashioned Riffs For Cold, Crisp Nights

*By James Hills — Updated September 2026*

September is National Bourbon Heritage Month, but honestly, whiskey is at its best in the colder months that follow. It has a comfort feel that warms you up on a cold, crisp day, and it goes great with harvest favorites like pumpkins, apples, and the berries that make it through the first few cold nights. These fall whiskey cocktails came in from distillers, bartenders, and brands, along with five riffs on the same classics that trade whiskey for rum, brandy, or gin.



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Half of these recipes call for a flavored syrup, and a Sunday afternoon at the stove covers most of them. Keep them in labeled jars in the fridge and use them up within a few weeks.




- **Cinnamon syrup** - simmer one cup of sugar, one cup of water, and three or four cinnamon sticks for 10 minutes, then let it steep until cool and strain.

- **Rich demerara syrup** - two parts demerara sugar to one part water gives stirred whiskey drinks more body than plain simple syrup.

- **Honey syrup** - thin honey with warm water so it mixes into a cold drink instead of sinking to the bottom of the glass.

- **Chai syrup** - steep three chai tea bags in a cup of hot simple syrup for 10 minutes for an instant baking-spice sweetener.

- **Real maple syrup** - buy the dark, robust grade instead of pancake syrup, which is mostly corn syrup and flavoring.





1. [Ancho Old Fashioned by Ancho Reyes](https://www.mantripping.com/food-and-drink/fall-whiskey-cocktails.html#ancho-old-fashioned-by-ancho-reyes)
2. [Spiced Orchard Old-Fashioned by Ovide at Hotel Effie Sandestin](https://www.mantripping.com/food-and-drink/fall-whiskey-cocktails.html#spiced-orchard-old-fashioned-by-ovide-at-hotel-effie-sandestin)
3. [Caramelized Apple Rye Fest by Filmland Spirits](https://www.mantripping.com/food-and-drink/fall-whiskey-cocktails.html#caramelized-apple-rye-fest-by-filmland-spirits)
4. [Pumpkin Pie Martini by Jeptha Creed Distillery](https://www.mantripping.com/food-and-drink/fall-whiskey-cocktails.html#pumpkin-pie-martini-by-jeptha-creed-distillery)
5. [The Balvenie Harvest Honey by The Balvenie](https://www.mantripping.com/food-and-drink/fall-whiskey-cocktails.html#the-balvenie-harvest-honey-by-the-balvenie)
6. [Glenfiddich Speyside Cobbler by Glenfiddich](https://www.mantripping.com/food-and-drink/fall-whiskey-cocktails.html#glenfiddich-speyside-cobbler-by-glenfiddich)
7. [Old Fashioned And Negroni Riffs That Trade Whiskey For Rum, Brandy, Or Gin](https://www.mantripping.com/food-and-drink/fall-whiskey-cocktails.html#old-fashioned-and-negroni-riffs-that-trade-whiskey-for-rum-brandy-or-gin)[Desert Night Old Fashioned by Vara](https://www.mantripping.com/food-and-drink/fall-whiskey-cocktails.html#desert-night-old-fashioned-by-vara-winery-and-distillery)
8. [Festive Old-Fashioned by LT Steak and Seafood](https://www.mantripping.com/food-and-drink/fall-whiskey-cocktails.html#festive-old-fashioned-by-lt-steak-and-seafood)
9. [Spiced Daiquiri by Don Q Rum](https://www.mantripping.com/food-and-drink/fall-whiskey-cocktails.html#spiced-daiquiri-by-don-q-rum)
10. [Boatyard Double Gin Negroni by Boatyard Distillery](https://www.mantripping.com/food-and-drink/fall-whiskey-cocktails.html#boatyard-double-gin-negroni-by-boatyard-distillery)
11. [Negroni by Devil's Grin Texas Gin](https://www.mantripping.com/food-and-drink/fall-whiskey-cocktails.html#negroni-by-devils-grin-texas-gin)

[How To Use The Upcoming Winter Months To Build Your Own Unique Whiskey Cocktails](https://www.mantripping.com/food-and-drink/fall-whiskey-cocktails.html#use-this-winter-to-build-your-own-whiskey-cocktails)
1. [Pick A Dry Apple Over A Sweet One](https://www.mantripping.com/food-and-drink/fall-whiskey-cocktails.html#pick-a-dry-apple-over-a-sweet-one)
2. [Roast Acorn Squash Instead Of Pumpkin](https://www.mantripping.com/food-and-drink/fall-whiskey-cocktails.html#roast-acorn-squash-instead-of-pumpkin)
3. [Change One Ingredient At A Time And Experiment](https://www.mantripping.com/food-and-drink/fall-whiskey-cocktails.html#change-one-ingredient-at-a-time)


Most of these drinks need nothing more than a shaker or a mixing glass, which makes them easy to pour for a guys night by the fire pit or for work colleagues at a fall open house. Pour them slowly, and make sure everybody has a ride home. If you want the smoke from the grill in your glass, the [Knob Creek BBQ Old Fashioned](index.php?option=com_content&view=article&id=4721:knob-creek-bbq-old-fashioned&catid=17:food-drink&Itemid=529) is my grill-side pick. And if the whiskey drinker in your life needs a better home bar, our [gifts for the whiskey dad](index.php?option=com_content&view=article&id=4703:fathers-day-gifts-for-the-whiskey-dad&catid=16) start with a cocktail smoker kit.





## Ancho Old Fashioned by Ancho Reyes


This Old Fashioned splits the base between Wild Turkey 101 bourbon and Ancho Reyes Original, the chile liqueur made from ancho chiles in Puebla, Mexico. The result is spiced and a little smoky, built for sweater weather next to a campfire. The same liqueur shows up in a few of our [spicy cocktail recipes](index.php?option=com_content&view=article&id=4623:three-spicy-cocktails-to-shake-up-national-cocktail-day&catid=17:food-drink&Itemid=529).








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**Ingredients**




- 1 part Ancho Reyes Original

- 1 part Wild Turkey 101 Bourbon Whiskey

- 1/4 part rich simple syrup

- 2 dashes Angostura bitters

- 2 dashes orange bitters



**Method**




1. Stir all ingredients in a mixing glass with ice until chilled and properly diluted.

2. Pour into a rocks glass over a large ice cube and garnish with an orange twist.



More at [Ancho Reyes](https://www.anchoreyes.com/drinks/old-fashioned/).


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## Spiced Orchard Old-Fashioned by Ovide at Hotel Effie Sandestin


Ovide at Hotel Effie Sandestin, on Florida's Emerald Coast, builds its fall Old-Fashioned on Elijah Craig bourbon with green apple liqueur and cinnamon syrup. It's shaken rather than stirred, which makes it a little lighter and colder than a stirred version.


**Ingredients**




- 1.5 oz Elijah Craig bourbon

- 1 oz green apple liqueur

- 1 oz cinnamon syrup

- 2 dashes Angostura bitters



**Method**




1. Combine all ingredients in a cocktail shaker with ice and shake until cold.

2. Strain into a rocks glass and garnish with a cinnamon stick.



More at [Ovide](https://www.hoteleffie.com/dining/ovide).





## Caramelized Apple Rye Fest by Filmland Spirits


Filmland Spirits sent this recipe with a movie-style backstory about a bartender saving the world from an army of robot mixologists. The drink itself is a rye highball with a torched green apple slice, half muddled into the whiskey and half left on top to eat.


**Ingredients**




- 2 oz Filmland Spirits Ryes of the Robots Extended Cut

- 3/4 oz fresh lemon juice

- 1/2 oz brown sugar and cinnamon syrup

- 2 dashes aromatic bitters

- 2-3 oz club soda

- 1 slice green apple, about 1/4 inch thick, and brown sugar for caramelizing



**Method**




1. Coat the top of the apple slice with brown sugar and caramelize it with a kitchen torch until it bubbles and turns golden, then cut it in half.

2. Muddle one half gently into the rye in a shaker.

3. Add the lemon juice, syrup, bitters, and ice, and shake until well chilled.

4. Strain over fresh ice in a rocks or highball glass, top with club soda, and stir gently.

5. Garnish with the other half of the caramelized apple.



More at [Filmland Spirits](https://www.filmlandspirits.com/).





## Pumpkin Pie Martini by Jeptha Creed Distillery


Jeptha Creed Distillery in Shelbyville, Kentucky, is an easy stop on a bourbon guys trip out of Louisville, and its wheated bourbon anchors this dessert in a glass. Pumpkin purée and egg white give it body, and a chocolate ganache and graham cracker rim stand in for the pie crust.


**Ingredients**




- 2 oz Jeptha Creed Wheated Bourbon

- 2 dashes Ne Oublie Black Walnut Bitters

- 1 oz egg white

- 1/2 oz spiced simple syrup

- 1 oz pumpkin purée

- Graham cracker crumbs and chocolate ganache, for the rim



**Method**




1. Rim a martini glass with ganache and graham cracker crumbs and chill it.

2. Add all ingredients to a shaker and shake without ice.

3. Add ice and shake again.

4. Double strain into the martini glass.



More at [Jeptha Creed](https://jepthacreed.com/product/six-year-old-wheated-bourbon/).





## The Balvenie Harvest Honey by The Balvenie


The Balvenie's recipe keeps the Scotch in front. The Sweet Toast of American Oak 12 Year Old gets a half measure of Pineau des Charentes, a fortified wine from France's Cognac region, plus spiced honey and molasses bitters, so it drinks like a richer version of the whisky itself.


**Ingredients**




- 2 parts The Balvenie Sweet Toast of American Oak 12 Year Old

- 1/2 part Pineau des Charentes

- 1 bar spoon spiced honey

- 3 dashes molasses bitters



**Method**




1. Add all ingredients to a mixing glass with ice and stir briefly.

2. Strain into a coupe glass.



More at [The Balvenie](https://www.thebalvenie.com/en-us/).





## Glenfiddich Speyside Cobbler by Glenfiddich


The cobbler is an old sherry-and-crushed-ice drink, and Glenfiddich doubles down by pairing its 12 Year Old Sherry Cask with an equal pour of amontillado sherry. With half the base being sherry, it drinks lighter than an all-whisky cocktail.


**Ingredients**




- 1.5 parts Glenfiddich 12 Year Old Sherry Cask

- 1.5 parts amontillado sherry

- 1/2 part simple syrup

- Half-wheel of orange



**Method**




1. Add the whisky, sherry, orange half-wheel, and simple syrup to a shaker with ice and shake for about 30 seconds, until the tin is cold.

2. Strain into a Collins glass filled with crushed ice.

3. Garnish with a dark maraschino cherry.



More at [Glenfiddich](https://www.glenfiddich.com/).



## Old Fashioned And Negroni Riffs That Trade Whiskey For Rum, Brandy, Or Gin


Not every good fall stirred drink starts with whiskey. These five swap in aged rum, brandy, or gin, and each one sits a short step away from a whiskey classic you already know how to make.





### Desert Night Old Fashioned by Vara


Distiller Ayisha Mares at New Mexico's Vara Winery & Distillery makes a textbook Old Fashioned with Vara's aged rum or brandy, with an optional dash of chocolate bitters.


**Ingredients**




- 2 oz Vara aged rum or Vara brandy

- 1/4 oz brown sugar syrup (equal parts brown sugar and warm water)

- 2 dashes aromatic bitters

- 1 dash chocolate bitters (optional)

- Orange peel, to garnish



**Method**




1. Stir the spirit, syrup, and bitters in a mixing glass with ice for 20-30 seconds.

2. Strain into a rocks glass over one large ice cube.

3. Express the orange peel over the drink, rub it around the rim, and drop it in.



More at [Vara](https://varawines.com/).



### Festive Old-Fashioned by LT Steak and Seafood


Chef Laurent Tourondel's LT Steak & Seafood at The Betsy Hotel on Miami Beach's Ocean Drive pours this one for fall: Brugal 1888 rum from the Dominican Republic, chai syrup, and bitters, finished with star anise.


**Ingredients**




- 2 oz Brugal 1888 rum

- 1/2 oz chai syrup (Monin recommended)

- 2 dashes Angostura bitters

- 1 star anise, to garnish



**Method**




1. Add all ingredients to a mixing glass, top with ice, and stir for 15-20 seconds.

2. Strain over one large ice cube in a rocks glass and garnish with the star anise.



More at [LT Steak & Seafood](https://www.thebetsyhotel.com/dine/lt-steak-seafood).





### Spiced Daiquiri by Don Q Rum


Don Q Oak Barrel Spiced from Puerto Rico turns the summer daiquiri into a fall drink, with vanilla syrup and a couple of drops of bitters. It's the brightest drink in this section.


**Ingredients**




- 1.5 oz Don Q Oak Barrel Spiced

- 1.5 oz lime juice

- 3/4 oz vanilla simple syrup

- 2 drops Angostura bitters



**Method**




1. Shake all ingredients hard with ice.

2. Strain into a chilled coupe.



More at [Don Q](https://donq.com/don-q-oak-barrel-spiced/).





### Boatyard Double Gin Negroni by Boatyard Distillery


Boatyard Distillery in Northern Ireland sent the standard equal-parts Negroni on its Double Gin. Swap the gin for bourbon and you've made a Boulevardier, the Negroni's whiskey cousin.


**Ingredients**




- 1 oz Boatyard Double Gin

- 1 oz sweet vermouth

- 1 oz Campari



**Method**




1. Stir over ice and strain into a rocks glass filled with fresh ice.

2. Garnish with an orange twist or orange slice.



More at [Boatyard Distillery](https://www.boatyarddistillery.com/shop/double-gin-20cl).





### Negroni by Devil's Grin Texas Gin


Devil's Grin takes its name from the mesquite tree's nickname, "the Devil with Roots," and its 14 botanicals put citrus ahead of juniper. That gives the gin enough character to stand up to Campari.


**Ingredients**




- 1 oz Devil's Grin Texas Gin

- 1 oz sweet vermouth

- 1 oz Campari

- Fresh orange slice, to garnish



**Method**




1. Stir all ingredients in a mixing glass with ice for 30 seconds.

2. Strain into a rocks glass over one large ice cube and tuck in the orange slice.



More at [Devil's Grin](https://devilsgringin.com/).



## How To Use The Upcoming Winter Months To Build Your Own Unique Whiskey Cocktails


Fall is here and while most people look at it as the end of warm weather and summer fun, it's also a great time to start unwinding and relaxing and taking some precious moments to try something new while you wait for spring to arive. You've got an entire winter ahead of you to play around inside, so take this time to create something new. The drinks above are a starting point, and a few small changes will turn them into cocktails that are yours.



### Pick A Dry Apple Over A Sweet One


It's tempting to dismiss apple cocktails and apple versions of spirits as overly sweet, but apples can be dry too. A tart Granny Smith or a splash of dry hard cider brings acid instead of sugar, which is exactly why the Filmland recipe calls for green apple. Try topping a rye highball with dry hard cider instead of club soda.



### Roast Acorn Squash Instead Of Pumpkin


Pumpkin gets all the attention, but acorn squash is nuttier and less watery. Halve one, roast it cut side down at 400 degrees for 40 to 45 minutes, scoop it out, and blend it smooth. Use it one-for-one in place of the pumpkin purée in the Pumpkin Pie Martini.



### Change One Ingredient At A Time And Experiment


Keep a base Old Fashioned you know by heart: 2 oz whiskey, 1/4 oz syrup, and 2 dashes of bitters. Each weekend, change only the syrup or only the bitters and write down what happened. By spring you'll have a house cocktail your buddies ask for by name.


Whatever you choose to do, do it deliberately! Take the time to try something new and maybe you'll discover something new about yourself and what you like or that by trying an ingredient from a different part of the world that it opens you up to planning a trip there ... Ancho Reyes from Mexico to add a smoky sweet heat, some Orange Blossom Water from North Africa, Yuzu Juice from Japan or Guarana Syrup from Brazil to give your drink a sweet kick of energy. Try something new and enjoy experimenting with fall whiskey cocktails!

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                    Written by: James Hills








        Published: 22 September 2026







        Last Updated: 25 September 2026

























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*Source: [11 Fall Whiskey Cocktails And Old Fashioned Riffs For Cold, Crisp Nights](https://mantripping.com/food-and-drink/fall-whiskey-cocktails.html)*

**Tags:** Bourbon, Whiskey, Cocktails, cocktail recipe, rum, Drinks
