Grace Gaelic Hospitality
365 Third Ave., nr. 26th St.; 646-918-6553
The new kid in town, Grace Gaelic Hospitality was founded as a tribute to Irish culture and to Grace O’Malley, the Pirate Queen of Ireland. It’s hard to make out the Gaelic crests and maps of Ireland amid the dark wood booths and dimly lit bar, but there are candles to guide you through the classed-up pub, and the menu — though not super Irish — delivers. At the bar, try one of twelve odes to Grace O’Malley, created by twelve female mixologists, like the dark-bodied Irish Whiskey–based Westport he sherry-based Granny O’Malley is also a good drink to sip until closing.
The Dead Rabbit
30 Water St., nr. Broad St.; 646-422-7906
This FiDi saloon from Sean Muldoon and Jack McGarry functions as a kind of new-school, tipsy exaltation to Gotham’s legacy of Irish immigrants. Downstairs, in a sawdust-scattered taproom hung with murals of the 69th Regiment, bartenders pour ales like Green Flash West Coat IPA and glugs of native whiskey (Connemara, Tullamore Dew). Upstairs, McGarry tends to a massive list of cocktails that may just be the city’s most ambitious: The rigorously historical menu spans punches, absinthe, nogs, slings, smashes, and more, each dutifully footnoted, thoughtfully prepared, and—most significantly—damn delicious.
205 E. 4th St., nr. Ave B.; 212-979-0900
At this unabashedly bookish East Village bar, opened on New Year’s Eve by the great-grandnephew of Oscar Wilde, no less, drinkers can unleash their inner English majors under the watchful portraits of famous scribes from Milton to Miller. (If you can name fifteen of those writers, your drink is on the house.) The theme continues from the house beer, Dorian Gray Amber ($5), to the Paradise Lost–papered bathroom.
Molly's Pub and Sheebeen
287 Third Ave., nr. 22nd St.; 212-889-3361
Describe Molly's to your friends and you'll sound like you're parroting all the clichés about an "authentic" Irish pub: stern but jovial bartender, sawdust on the wooden floor, Irish tunes on the jukebox, etc., etc. But convince them to come here and they'll realize that Molly's is the kind of place that inspires clichés (and scores of clichéd imitators), not obeys them. Don't be surprised if your "just one pint" turns into five or six—especially in winter, when the fireplace is crackling.
The Dead Poet
450 Amsterdam Ave., nr. 82nd St.; 212-595-5670
Nestled in among a strip of boisterous college bars on Amsterdam Avenue, this narrow little nook has big literary ambitions. The owner, Drew Dvorkin, was once an English teacher, and as a nod to his academic past, he's hung framed verses from Dickinson, Donne, and Joyce on the walls. The total space isn't wide—it's barely 10 feet across; getting jostled when you move down the 20-foot bar is unavoidable on crowded nights. But once you've made it to the other side, there's a popcorn machine to reward your efforts, as well as seventeen respectable beers on tap and a wide selection of Irish whiskeys.
57-24 Roosevelt Ave., at 58th St., Woodside; 718-429-9339
A welcoming, sometimes boisterous Irish tavern has commandeered this corner of Queens as far back as locals can remember, and it has been known as Donovan's since 1966. Behind the beer-centric bar is a Celtic labyrinth of rooms with tall dark-wood booths, stained-glass windows, and fireplaces. Waitresses wear brogues. But Donovan's is more than an archetypal pub for old-school types. It serves, arguably, the best burgers in the five boroughs: Juicy, flavorful, char-broiled half-pounders, with home-cut steak fries. At some bars, everyone knows your name. At Donovan's, everyone knows what to order.
1590 Second Ave., nr. 83rd St.; 212-203-2751
With pillow-lined benches, framed old portraits, and ornate typewriters on display, the Penrose can feel like a quaint countryside getaway. The menu matches the bar’s warmth, with a cocktail list featuring drinks like the “Old Pal Spencer” (bourbon, aperol, sweet vermouth, a large ice cube, and a twist of orange) and the Dirty Pickle Martini, garnished with, well, a pickle. The real treat is a whiskey list with over 50 options, like the 18-year-old Highland Park single malt. It hangs out behind the bar with the coveted Pappy Van Winkle bourbon. Penrose usually has their hands on a few bottles, sometimes even the 23-year.