Cooler Temps, Warming Cocktails

No Booze Sews a Liquid Blanket Quite As Nice As Whiskey

After months of hydration coming primarily as rosés, beach beers, and various forms of the spritz, the seasons are changing – and so should what’s in your glass. It’s time to put the coolers away and bring out the tumblers for fall’s favorite golden-hued tipple. And with that, we bring you six whiskey cocktails that will keep you heated from the inside out.

The Scorpios at Calissa (1020 Montauk Hwy., Water Mill)

Perhaps the most notorious of the astrological signs, Scorpios have a reputation for being, shall we say, Machiavellian – often either loved or feared for their intensity and passion. This is all to say that The Scorpios cocktail at Greek taverna Calissa is devilishly delicious, but it isn’t for the weak of heart. Vanilla and kaffr lime give this drink a sweet start, but underneath, the mix of rum and bourbon is piercing. Needless to say, if you’re after a Dionysian time, this is your drink, and Calissa is your spot. Family-style sharing plates – mezze platters, faro and watermelon salads, long plates of salt-baked fish drenched in olive oil – provide some of the best Greek fare around, tiding you over until live gypsy jazz musicians or Mykonos-vibe DJs start playing later at night.


The Brigantine at The Crow’s Nest (4 Old West Lake Dr., Montauk)

The Crow’s Nest Inn may well be Montauk’s best hidden gem, a Bohemian dream of a boutique hotel tucked away in a quiet part of town. Being the brainchild of Sean McPherson, hotelier behind Manhattan’s Bowery and Marlton hotels, not a detail of its barefoot-luxury style was overlooked, rendering it as much equipped
for the colder reaches of year as the warm. On cool, quiet nights, there are fireplaces aglow inside, firepits under the night sky, and candles flickering on seemingly every surface, sure to put you in a freer spirit if you weren’t in one already. Aiding the process is the double rye–based Brigantine, made sweet and tart with Amaro, Cocchi Americano (a quinine-tinged wine), and grapefruit bitters, which pairs perfectly with food from the organic restaurant and the sound of waves crashing in the distance.


The Bourbon Swayze at Rushmeyer’s (161 Second House Rd., Montuak)

The Crow’s Nest recalls vibes of Almost Famous, Ruschmeyer’s hotel summons up the summer camp from Wes Anderson’s Moonrise Kingdom. Three acres of wooded lands by Fort Pond are fitted out with bicycles and lawn games, fairy lights and hammocks, and a large restaurant set in a mess hall–esque dining room with
a pitched wooden roof and checkered linens despite its upscale fare. Right in line with the rest of its playful persona, Ruschmeyer’s also boasts one of the most fun after-dark scenes in the Hamptons, often throwing dance parties and special events throughout the summer season. Things quiet down a bit in fall – and the property closes annually for winter – but it still welcomes any and all who wish to come and sip a few Bourbon Swayzes by a fire and strum a guitar or watch the stars.


The 65 Mustang at Union Cantina (40 Bowden Sq., Southampton)

Like any good Mexican establishment, Union Cantina is in the business of getting you a buzz along with your gourmet short rib tacos, be that with one of its myriad margaritas, fresh fruit sangria, or otherwise. Arguably the least Mexican of the cocktail options here, the 65 Mustang is nevertheless our choice for fall, an apple bourbon drink that adds a unique twist on the classic spiced cider with bitters, mint, and fresh lime. It will remind you to put an apple-picking afternoon on your agenda, it will cut the spice from your jalapeno- topped nachos, and best of all, it will get you well and pre-gamed for when you head downstairs to continue the night at the 400 Rabbits speakeasy bar on-site. It may not be the most south-of-the-border option on the menu, but after two or three, does it matter?