Entertaining

7 Underrated Classic Cocktails That Are Perfect for Fall

You’re probably only familiar with applejack within the context of a Jack Rose, if at all, but the potent apple brandy is key to a wide variety of drinks. The Honeymoon was invented in 1916, but didn’t gain popularity until the ‘20s at the iconic Brown Derby restaurant. Essentially an Apple Brandy Sour, the drink calls for a mix of applejack, orange curaçao, Bénédictine and fresh lemon juice.

The iconic Manhattan is a perfectly delectable cocktail to sip in the fall, but the sweet Saratoga is even better suited for the season. The variation appropriates the Manhattan’s traditional combination of sweet vermouth and spicy Angostura bitters, but swaps out whiskey for a split of rye and Cognac, which gives the cocktail a richer, more fruit-forward flavor.

With all of fall’s decadent food offerings, not to mention the gluttonous holiday of Thanksgiving, you’ll need a nice aperitif to whet your appetite. The mid-19th century Adonis Cocktail fits the bill, with a simple blend of dark, nutty oloroso sherry and sweet vermouth—plus a few dashes of orange bitters that simultaneously lighten things up and add more depth.

Not all tiki cocktails call from rum. Nor should they all only be consumed in the summer. The Poison Dart blends bourbon with spicy cinnamon syrup and pimento dram, along with fresh lemon, creamy orgeat, orange bitters and earthy Cynar. While no one really knows the origins of this cocktail, we’re just grateful it exists to inject some sunny tiki flair into brisk autumn days.  

A riff on a Rob Roy (which is, in itself, a riff on the Manhattan), the Bobby Burns stirs blended scotch with sweet vermouth—just like a Rob Roy—but adds a splash of herbaceous Bénédictine. Smoky, honeyed and ideal for lazy fall evenings in, the full-bodied Bobby Burns will convince you to cheat on Rob Roy every time.

Not to be confused with its lightweight cousin Sangria, Sangaree was first made in the 1700s by Spanish merchants who mixed red wine with Batavia Arrack, citrus and nutmeg. A few adjustments to the historical version make it perfect for modern times. This recipe for Sangaree mixes port wine with dark rum, applejack and maple syrup, along with a few dashes of Angostura bitters. Garnish with a skewer of slivered apples and, as the old merchants did, a dusting of freshly grated nutmeg.

Don’t let the sweet, herbal flavor of the Diamondback Cocktail fool you; this all-booze cocktail packs a punch. A potent mix of rye whiskey, apple brandy and green Chartreuse, the 1950s-era Diamondback Cocktail is extremely drinkable, thanks to the sweet, fruity brandy. Sip it after dinner to unwind at the end of a long day this fall, and warm up from the inside out.