Nightcap Happy Hour with Kara Newman and 

Brothers Vilgalys

February 19, 6 to 8 p.m., free with RSVP

The Durham Hotel, Durham

“How about a nightcap?” There’s a lot wrapped up in that question, but whether you’re looking to close out the night or keep it going, the nightcap is not just a singular entity. As author Kara Newman explores in her latest book, Nightcap (Chronicle Books), the modern nightcap is much more nuanced than its ‘wink, wink’ reputation, and it’s gaining a larger foothold in our drinking culture. To wit, the book showcases more than forty recipes from bartenders around the country: some that are boozy, some that could double as dessert, a few to keep the conversation going, some that aid digestion, and several to send you to sleep.

We spoke to Newman by phone in advance of her upcoming book event at The Durham on February 19, when the bar team will be mixing up cocktails inspired by the book and featuring spirits from Durham distiller The Brothers Vilgalys (snacks are provided, cocktails available for purchase). Here, Newman shares her definition of the modern nightcap, how it got a bad rap, and the book’s best surprises and rule-breakers.

INDY: You’ve written books about batch cocktails (Cocktails for a Crowd), equal parts cocktails (Shake. Stir. Sip.), making cocktails on the go (Road Soda), among others. What made you want to write about nightcaps?

KARA NEWMAN: The short answer is that there hadn’t been anything done on it recently. It just seemed it was time for a more modern take on the nightcap and its role in our drinking landscape.

As you point out, nightcaps aren’t really a category or a style. It’s more about timing and personal circumstances. How did you end up defining the nightcap?

I talked to a lot of bartenders, and I thought about the role of a nightcap and finally landed on the idea that it’s not just a singular style of drink. Sometimes, it’s not even a cocktail at all; sometimes it’s just a simple, straight pour.

How people interact with a nightcap was interesting to tackle. For some, it’s about ending an evening at home, for some it’s about winding down a meal at a restaurant, for others, it may play more of a dessert-style role. It also plays a role in extending conversation.

I thought that a nightcap was always going to be something stirred and boozy. One of the big surprises for me was that sometimes people prefer a low-alcohol or even a no-alcohol nightcap. Or it can be caffeinated, because people take coffee at the end of a meal. There were a surprising number of nightcap recipes that had caffeine.

Is there one that was particularly surprising to you?

The Fernet Flip was one of the catalysts for the book. I was in Chicago for a work event, and my husband and I were having a nice end-of-night drink at the bar. I was astonished that there were so many people still up on a random Tuesday night, and everyone was ramping up. The bartender made this drink for me from the “end of the night” part of the menu. It’s made with cream, eggs, and a local fernet that was a collaboration with a local coffee roaster. It tasted like espresso in a glass; it was comforting and dessert-like.

The bartender said to me, “We sell a lot of this drink and a lot of drinks off this portion of the menu, because lots of people are coming in for a ‘nightcap,’” and he said that in air quotes. They’re really pausing before they party on for the rest of the night.

Your book is about the modern-day nightcap. What is the nightcap’s historical significance, and how has the nightcap changed?

The earliest nightcaps weren’t called nightcaps. They’ve been around for as long as we’ve had access to alcohol or any kind of drinking culture. The word “night cap”—something to keep your head warm when you’re sleeping—came into existence in the 1800s well before “nightcap” as a drink.

In terms of nightcap as a drink, I came across a book from the 1800s from Oxford University called Nightcap. The drinks in there are not specifically nightcaps, but they’re still drinks that would’ve been appropriate for drinking as a nightcap, like a lot of port, a lot of drinks made with eggs and cream—a lot like that Fernet Flip. It wasn’t uncommon in the 1800s and early 1900s for drinking to take place at the beginning of the day or to take place all day long, right until the Temperance movement when things became a little more regulated and drinking became a nighttime thing with a bit of festive daytime drinking here and there.

At that point, there’s this whole mid-century “wink wink, come back to my place and have a nightcap baby.” It doesn’t do the nightcap any favors. It’s not about the drink, it’s about what it’s for—I’ll leave that to your imagination.

The Paper Planes Shots is an interesting, modern take. What’s the story there?

The Paper Plane is a lovely drink on its own. It’s a riff on the Last Word cocktail, which is a classic equal parts cocktail. It’s Aperol, bourbon, amaro, and lemon juice. I went to the Four Seasons bar (now The Grill) and was sitting at this long, elegant bar in midtown Manhattan. There were two couples partying hard. They’d been there for a while, and the bartender was clearly ready for them to go, but he was trying to send them off in a good frame of mind. He gave them their check and poured out four little shots of this pink liquid. They toasted and cheered, then they paid their bill and left. It turned into a very festive sendoff. It was their nightcap.

At the same time, here’s this drink that kind of violates every “rule” you might have set up for the nightcap genre. It’s a sour, it’s not a straight pour of anything, it’s bright pink, and it seems a little too stimulating, but it was perfect in that moment.

What nightcaps will be served at your upcoming event at The Durham?

The bar team came up with cocktail specials inspired by the book and featuring spirits from The Brothers Vilgalys. They are doing an interpretation of The Nineteenth Century, called The Fifteenth Century. It will have tequila and mezcal instead of bourbon, as well as Zaphod, a tropical fruit liqueur. They’re also doing the Suppressor No. 246, which is a style of lower-alcohol cocktails. Instead of honey, they’re using the Krupnikas honey liqueur, and in lieu of the chai infusion, they’re adding a chai-inspired infused vermouth. They’re putting a local spin on it, which I’m 100 percent in favor of.