Fall arrives like a blanket of red, gold, and orange leaves. It’s a time for warm sweaters, long pants, short days, and long nights. The air is getting crisper, and the ever-present aroma of a backyard campfire wafts from somewhere nearby. If you live somewhere that actually has seasons, it’s a beautiful time of year before the eventuality of snow. It’s also the perfect time to start shaking and stirring up warming whiskey-based cocktails.
In my years of writing about alcohol, I’ve found that there’s no better season for whiskey than autumn. Sure, winter has its place when it comes to drams of single malt Scotch whisky, bourbon, and rye. But fall is when temperatures can range from summery to frigid from day to day. If you ask me, that’s the best weather for whiskey drinks.
Why is autumn whisky cocktail season?

You might be wondering why whiskey is the proverbial king of fall cocktails. There are several reasons for this. For one thing, barrel aging adds flavors like charred oak, toasted vanilla beans, caramelized sugar, and baking spices (and peppery rye in the case of rye whiskey). These flavors complement fall weather. On top of that, whiskey is known for its warming finish. This is especially true if you’re mixing cask-strength, barrel-proof, or bottle-in-bond whiskeys.
Lastly, whiskey pairs well with fall flavors like orchard fruits, maple syrup, cinnamon, and baking spices. All in all, it’s the absolute best choice for autumnal mixing.
How I pick my fall whiskey-based cocktails

If you paid close attention to the background on why whiskey is great for autumn, you should have a decent idea of why I selected certain cocktails. In the fall, I look for warming, balanced, boozy, flavorful cocktails. While it is not a necessity, I also look for fall flavors.
The best whiskey-based cocktails to drink this autumn

Luckily, there are seemingly countless whiskey-centric cocktails well-suited for fall sipping. These include single malt Scotch whisky, bourbon, rye, and other whiskeys, plus seasonal flavors and warming spices. Below is my list of go-to fall whiskey drinks. Keep scrolling to see them all.
Penicillin

If you only make one whiskey-based cocktail this fall, make it the epically flavorful Penicillin. Australian-born bartender Sam Ross created this contemporary masterpiece in 2005 at the New York City cocktail bar Milk & Honey. This drink of blended Scotch whisky, fresh lemon juice, honey-ginger syrup, and a peated Scotch whisky float quickly became popular at bars throughout the world and remains a beloved drink 2 decades later.
Ingredients:
2 ounces blended Scotch whisky
.75 ounces fresh lemon juice
.75 ounces honey-ginger syrup
Peated single malt Scotch float
Lemon twist garnish
Preparation: In an ice-filled cocktail shaker, add the blended Scotch whisky, fresh lemon juice, and honey-ginger syrup. Shake vigorously to combine and chill. Strain into a rocks glass over one large ice cube. Pour peated single malt Scotch over the back of a bar spoon to make a float. Garnish with a lemon twist.
Maple Old Fashioned

As the name suggests, this is a fall version of the classic cocktail. While the Old Fashioned dates back to the 1800s, the Maple Old Fashioned is a contemporary take that swaps simple syrup for maple syrup. This autumnal version also features rye whiskey and Angostura bitters.
Ingredients:
2 ounces rye whiskey
.5 ounces pure maple syrup
3 dashes Angostura bitters
Garnish with an orange twist.
Preparation: In an ice-filled mixing glass, add the rye whiskey, pure maple syrup, and Angostura bitters. Stir gently to combine and chill. Strain into an Old Fashioned glass over one large ice cube. Express the oils of orange peel over the rim of the glass and drop it into the drink.
Lion’s Tail

Created before Prohibition, the Lion’s Tail was first published in 1937 in William James Tarling’s “Café Royal Cocktail Book”. If you’ve never tried this seasonally appropriate drink, you’re missing out on the outstanding flavors of bourbon, allspice dram, fresh lime juice, simple syrup, and Angostura bitters.
Ingredients:
2 ounces bourbon
.5 allspice dram
.5 fresh lime juice
1 barspoon simple syrup
2-3 dashes Angostura bitters
Orange twist
Preparation: Add bourbon, allspice dram, fresh lime juice, simple syrup, and Angostura bitters to an ice-filled shaker. Shake vigorously to combine and chill. Strain into a chilled coupe glass. Garnish with an orange twist.
Paper Plane

Another modern-day classic from famed bartender Sam Ross, the Paper Plane was created in 2008 for the cocktail program at Chicago’s The Violet Hour. This elegant, warming cocktail combines bourbon, Aperol, Amaro Nonino Quintessentia, and freshly squeezed lemon juice.
Ingredients:
.75 ounces bourbon
.75 ounces Aperol
.75 ounces Amaro Nonino Quintessentia (or your favorite amaro)
.75 ounces freshly squeezed lemon juice
Garnish of lemon peel
Preparation: In an ice-filled cocktail shaker, add the bourbon, Aperol, Amaro Nonino Quintessentia, and freshly squeezed lemon juice. Shake vigorously to combine and chill. Strain into a chilled coupe glass. Express the oils from the lemon peel around the rim of the glass, then drop it into the cocktail.
Hot Toddy

Few cocktails are more appropriate for cool fall weather than the timeless Hot Toddy. While the modern-day Hot Toddy first gained popularity as a cold remedy in the early 1800s, this drink can trace its origins to 17th-century India, where it’s based on the “Taddy” drink made with fermented palm sap. The steaming hot drink we all know and love is made with whisk(e)y (usually blended Scotch whisky), honey, lemon juice, and hot water.
Ingredients:
2 ounces blended Scotch whisky
1 tablespoon honey
.5 ounces freshly squeezed lemon juice
Hot water topper
Garnish with a lemon wheel and cinnamon stick
Preparation: In a warmed mug, add honey and freshly squeezed lemon juice. Add the blended Scotch whisky. Top with hot water. Stir gently to combine all the ingredients and dissolve the honey. Garnish with a lemon wheel and a cinnamon stick.
Bottom line

By now, you’ve likely seen that myriad whiskey-based cocktails are well-suited for chilly fall weather. Make one or all of these drinks from now until the snow flies. You’re guaranteed to feel warm inside and out, even on the most frigid autumn nights.