Fall is here along with its seasonal hallmarks: leaves changing colors, blustery days, earlier evenings, and a vast array of pumpkin spice delights. Bourbon cocktails are also a terrific way to mark autumn’s entrance. The brown liquor can evoke the season’s warmth and coziness when paired with the right seasonal modifiers, making for a smooth transition from refreshing, rooftop-worthy cocktails or whatever your “drink of summer” ended up being.
It’s easy to sink into the season’s ambiance by immediately reaching for a classic like a traditional Old Fashioned or a Hot Toddy. That’s fine, of course — those drinks are familiar and excellent. But the world of bourbon cocktails includes a host of other under-the-radar options that can deliver exquisite fall vibes. Nobody knows this hidden gem-studded landscape quite like the pros, so we asked 14 bartenders to name their favorite underrated gems. These choices are a perfect way to enjoy the chillier months — or whenever the last heat wave rolls through your town.
The most underrated bourbon cocktails for fall, according to bartenders:
- Spiced Old Fashioned
- Lion’s Tail
- Maple Bourbon Smash
- Stone Fence
- Midnight Stinger
- A Clockwork Orange
- Autumn Sweater
- Black Manhattan
- Lonerider Cider
- Bourbon Smash
- Cock n Bull
- Boulevardier
“A Spiced Old Fashioned is a spiced-up twist on a classic. By adding the rich flavors of cinnamon and nutmeg, this seasonal adaptation captures the essence of autumn, infusing the classic cocktail with cozy, aromatic notes that evoke the comfort of a fireside evening. The warm spices complement the bourbon’s deep caramel and vanilla undertones, creating a balanced, smooth drink that’s both familiar and intriguing. Whether you’re toasting with friends or unwinding after a long day, this cocktail provides a comforting yet refined experience that perfectly captures the spirit of the season.” —Afzal Kaba, beverage director/director of mixology, Musaafer, Houston
“Lion’s Tail. It’s very crisp, autumnal, and delicious. We make ours with a bit of cheese foam and cocoa powder for an extra dessert-like element.” —Samatha Damianai, bartender, Bar Kamon, San Diego
“An underrated fall bourbon cocktail for me is a Maple Bourbon Smash. The simplicity of it makes it easy to make at home, and it brings a different twist on a familiar classic. With just bourbon, lemon, and a small amount of maple syrup, enjoying one of these cocktails is easier than watching the leaves fall. The smoky sweetness of the maple syrup especially pairs great with a nice, oaky bourbon.” —Jason Francis, director of food & beverage, The Harpeth, Franklin, Tenn.
“I’m a huge fan of a good Stone Fence: a simple highball made with a shot of bourbon over ice topped off with hard apple cider. I prefer mine with a dry French cider, but even sweeter American ciders work well here. For bonus points, keep your bourbon in the freezer and skip the ice. Doing this leaves room for more cider!” —Oliver Brooks, beverage operations team brand manager, Pappas Restaurants, Houston
“I think the Lion’s Tail is the drink of fall. It’s a Whiskey Sour with a little allspice dram to really bring in those fall flavors. It’s a favorite of [our] Speed Rack competitions and featured as one of the must-know classics in [our Speed Rack book] ‘A Quick Drink.’” —Ivy Mix, co-founder, Speed Rack/co-owner, Leyenda/FIASCO! Wine and Spirits/Whoopsie Daisy, Brooklyn
“One of my go-to bourbon drinks has long been the Midnight Stinger, a sour riff that pairs bourbon with Fernet-Branca. I first tried it years ago as a baby bartender who had only recently been introduced to Fernet, and I’ve been making it as a dealer’s-choice cocktail ever since. It’s usually a new cocktail for guests but it’s always a hit, even with folks that are not typically amaro drinkers. New Orleans falls are often still warm and muggy, so this cocktail’s bright mint and citrus notes can cut through the weather here while still feeling herbal and cozy. As a bonus, its simple build and ingredients makes it accessible at nearly any bar or as an at-home staple.” —Carly Lacoste, bartender, Beachbum Barry’s Latitude 29, New Orleans
“My favorite is A Clockwork Orange, made with bourbon, Cynar, Aperol, and orange-flower water. This autumnal take on a Boulevardier is a perfect sipper while wearing a flannel; it’s spirit-forward and leans more into the ‘bitter’ in bittersweet. Flavor-wise, it gives you a similar profile of dark-chocolate-covered oranges you may enjoy around holiday season.” —Trevor Langer, beverage director, Porchlight, NYC
“One of the most underrated fall bourbon cocktails would be an Autumn Sweater. I’m a huge fan of this one! It contains bourbon [or rye], Nonino amaro, Averna amaro, and maple. It’s perfect for the fall season with a nice balance of sweetness and bitterness.” —Travis Shook, beverage manager, Bacaro, St. Peters, Mo.
“My mind wanders to some of the classic bourbon cocktails like a Paper Plane or a New York Sour, but if someone is looking for something a bit more underrated, I would direct them towards a Black Manhattan. While a traditional Manhattan uses sweet vermouth, a Black Manhattan uses amaro, which gives it a bittersweet and well-balanced flavor and texture. That said, most Manhattans will be very booze-forward, which will always be a nice way to warm yourself up on a crisp Autumn evening.” —Tyler Flynn, beverage director, EsterEv, Milwaukee
“A Lonerider Cider, a Southwestern riff on the often-overlooked Whiskey Sour. This versatile rendition is made with maple, apple cider, and Warbringer Southwest Bourbon, and can roll with the sudden changes of fall weather. It can be served on ice during the day as a cooler or served hot at night as a warmer. Either way you serve it, it’s super delicious and easy to enjoy.” —Josh Goldman, co-founder, Soigne Group, L.A.
“My favorite underrated fall bourbon cocktail is the Bourbon Smash! For cooler seasons like the fall, I prefer using apple and pear to make one. It gives you the warmth from the bourbon and nutmeg and has a crisp finish with the apple, along with some citrus notes.” —Courtney Phillips, bartender, Revivalist at 106 Jefferson, Huntsville, Ala.
“The Cock n Bull is a go-to favorite of mine. Its origin bar tied [and] namesake, the Cock n Bull, was a popular pub in Hollywood and is also known for being the birthplace of the Moscow Mule. With a blend of bourbon and Ccognac, the drink is dark, velvety, and boozy. It’s a warm cashmere blanket in a glass and a great cocktail to play as your ‘last song of the night.’”—Sean Fitzmaurice, owner, Reserve 101, Houston
“The Lion’s Tail. A rarely ordered and often forgotten classic from the ’30s, this bourbon-forward sour with a finish of allspice is exactly what you need as the temperature drops and the leaves change.” —Michael Glassberg, bartender, The Press Room at The Eliza Jane, New Orleans
“When it comes to fall cocktails, I’d personally rather skip the apple cider and pumpkin spice and just settle down with a straightforward boozy cocktail like a Boulevardier. Just [build] with equal parts of your favorite bourbon, sweet vermouth, and Campari and voila — you have a sweater-sipper perfect for a fall day. I like using a higher-proof bourbon like Wild Turkey 101 in mine; that higher proof holds up and stands out against the bitterness of the Campari. If you’re feeling wild, try swapping the vermouth for mulled wine for that extra fall flair.” —Patrick Gibson, bartender, Jack Rose Dining Saloon, Washington, D.C.
