Ixcacao from Huckleberry Bar ($11)
Here's the thing about the Ixcacao hot chocolate at Huckleberry Bar: it burns all the way down. So much that, at first, you don't know if it's the heat, the peppermint-infused Chinaco Tequila, or any hidden spice in that chocolate that's making your throat tingle. Though it's boozy, the booze isn't all you're tasting, thanks to the hot chocolate itself—creamy on the tongue but not too thick, intensely chocolatey and a little bit minty. Both tasty and invigorating, this thing will warm you up.
Eggnog at Ward III ($12)
This homemade Maker's Mark eggnog flecked with freshly grated cinnamon and nutmeg is miles above standard. It's luxuriously but not overwhelming thick, with a whisper of orange and a hit of Averna.
Ward III is also serving a perfect hot toddy and bourbon-spiked cider with whipped cream.
Brown Butter Old Fashioned at Gramercy Park Hotel's Rooftop Bar ($18)
In the Gramercy Park Hotel's ivy-covered, glass-walled, and surprisingly not-crowded rooftop garden, bar manager Kevin Denton flavors Makers Mark using a technique called fatwashing. Browned butter is whisked into the whiskey and allowed to settle and chill overnight, after which the solidified fat is lifted off the surface, leaving the bourbon crystal clear, but with a distinct nutty, buttery nose. Served with a dash of house-made root beer bitters (the secret is lots of wintergreen) and Maraschino liqueur, it's a lively update that still respects the boundaries of the classic.
Hot Buttered Rye from Rye ($8)
You'd hope a place called Rye would know how to serve it, and they don't disappoint with a Hot Buttered Rye. Though many butter-based drinks can be oily or greasy-feeling, with globlues of fat on the surface, this drink integrates it totally so it's smooth and silken. With warming additions of Earl Grey and molasses, plus nutmeg and allspice and cloves, the Old Overholt Rye is mellowed but not at all obscured. Rich and spirit-forward, but terribly drinkable at the same time.
Koffie Van Brunt at Fort Defiance ($9)
Strong, earthy coffee spiked with Bacardi rum and Cherry Heering and topped with a cloud of cool whipped cream and a shaving of orange zest and nutmeg. It's decadent, roasty and rich, but not oversweet.
Clement's Shrub at Prime Meats ($13)
Apple cider vinegar is the key ingredient in this tart, refreshing bourbon cocktail (pictured on the right), which also includes fig preserves, lemon, apple cider, cinnamon, and cracked black pepper. Each sip is like biting into a caramel apple: juicy, sour, and sweet, with just a little spice.
Prime Meats also has a rotating hot punch available for $5. The one we tried was a soothing blend of brandy and bourbon, cloves, cider, honey, thyme, and rosemary.
The Deep Sea Diver from Hotel Delmano ($12)
Martinis know no season, but there's something particularly root-vegetable seasonal about the celery notes in the Deep Sea Diver, with Bitter End celery bitters, against Plymouth gin, Cocchi Americano (an aperitivo made from an aromatized moscato d’asti), and dry vermouth.
Hotel Delmano: 82 Berry Street, Brooklyn, New York 11211 (map); 718-387-1945
The Humble from Rye House ($12)
Lemon, honey, and basil may sound like summer flavors, but the real backbone of Rye House's Plymouth gin-based Humble cocktail is the Hum liqueur. It's an amaro-inspired rum-based botanical flavored with cardamom, ginger, and hibiscus that hits all the spicy, warming notes a good winter cocktail should.
Hot Chocolate Car Bomb at The Redhead ($9)
Cocoa laced with Jameson and Guinness? Yes, please. It's boozy, comforting, and rich. (The fluffy Baileys marshmallows on top push this drink decidedly into the dessert category; it's the kind of thing we want to drink with our fuzzy slippers on.)
Orchard Fizz at Gramercy Park Hotel's Rooftop Bar ($18)
At first sip, Gramercy Park Hotel's Orchard Fizz comes across as summery: lemony and bright with a slightly medicinal finish from the Angostura bitters. But once you get through the froth and bubbles added by the eggwhite and soda in this Applejack-based cocktail, the distinct flavor of pear and maple syrup comes through, placing it firmly back in the late fall/early winter category.