With the holidays come family—and with family comes drinking. But it doesn’t have be drinking alone, sneaking sips and shots between bouts with crazy siblings and upstart whippersnappers. Join
fellow escapees at the bar, where Happy Hour gives way to the Merry Season and
specialty cocktails spread good cheer.

SHENANDOAH /  STATE STREET EATING HOUSE

Within the noble confines of State Street Eating House, bartender Topher Nalefski plays alchemist atop his alcohol-infused throne, whipping up new flavors and combinations with manic abandon. Freshly returned from a cross-country exploration of cocktail culture, Nalefski dubs his latest concoction the Shenandoah cocktail, a riff on The Big Easy’s vieux carre. With rye whiskey serving as the backbone, Nalefski introduces a healthy portion of apple brandy—“It tastes like you’re walking in the forest picking apples”—and a helping of St. Georges Spiced Pear Liqueur to add some smooth sweetness alongside a little bite of spice. Finishing with Benedictine and two types of bitters—plum and black walnut—Nalefski burns a coating of yellow chartreuse in the glass before pouring, prompting an aromatic and moody fog to precipitate. “It’s very floral, very elegant,” says Nalefski. “I can’t wait for the first day it’s chilly, to sit and warm your hands with one.”

AFTER EIGHT / LOUIES MODERN

Holiday cocktails are a team effort at Louies Modern, with proprietor Joe Seidensticker, restaurant manager Rebecka Guilfoyle and mixologist Kaleigh Bellanger all coming together to revamp Louies’ cocktail menu for the season with wintry delights, including the After Eight. Beginning with equal parts Berentzen Bushel and Barrel apple-infused bourbon and St. Georges Spiced Pear Liqueur, the After Eight hits the ground running with bite and flavor before smoothing out with some Apple Pie Bitters, house-made sour and Cinnamon Bark Simple, a house-made simple syrup infused with cinnamon sticks. “The secret to any great cocktail is to have those flavors be clear,” says Louies Modern mixologist Matthew Jeronimo. “Even if there are three or four different items in play, you want to be able to taste your way through.” Chilled and poured with a sprinkling of nutmeg overtop, it smells like a Victorian Christmas, with a taste strongly reminiscent of spiced apples done right.

BLACK MANHATTAN /  THE GATOR CLUB

The folks at The Gator Club take a slightly different approach to the holiday season, not introducing a handful of seasonal specials but instead introducing the option to add that festive twist to your favorite bracer. It’s not one drink, it’s an atmosphere, and it’s all about “those little nuances,” says bar manager Josh Hojnacki. Take the Gator Club Black Manhattan, a twist on the traditional libation that retains that comfortable familiarity you want on the holidays, with a base of customary rye whiskey, sweet vermouth and bitters. However, for that mirthful winter’s kick, replacing some of that sweet vermouth with flavored liqueurs or amaros shifts the flavor profile. Hints of allspice, clove and cinnamon typically do the trick, evoking a holiday feel, says Hojnacki, as he’ll trade out citrusy bitters for clove bitters and darker amaros, such as Cynar, made from artichokes. “It’s all little ways to adjust those classics,” says Hojnacki. “To liven them up and make them more suited for the season.” And if the Black Manhattan isn’t for you, there’s still pumpkin vodka to play with. And Hojnacki can always fall back on the Irish Coffee. “Irish Coffees are great this time of year,” he says. “if it gets a little chill in the air.”