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The Woo Woo is an adults-only speakeasy close enough to Times Square that any New Yorker will get the ick. But if you can get over yourself, you ring a doorbell, speak the password (which you can find on their site), and then you’re almost there. You first have to pass through the shop, which is, to be clear, a sex shop replete with sex toys. All this before anything resembling a drink happens. If you’re bashful, this place isn’t for you.Â
The transition is the whole gag: a graffiti-lined descent, a red curtain, some neon light and that little thrill of being a wee bit daring and naughty. It’s supposedly '80s Times Square themed. I didn’t find it to be that exactly, but I get what it’s trying to evoke, and I appreciate it. Not everything we remember fondly was actually good. The schtick here is indeed fun to inspect and will definitely garner some giggles. Once you’re actually inside the bar, things do tone down. There’s a bunch of little tables to sit at, some lounge seating, and a bar with stools that have backs. It’s low-lit and comfy, campy fun, a gaze back at the Deuce from a safe remove. Yeah, it’s whitewashing and romanticizing the shit out of a time and place. But what is history if not grist for the mill? This is what Times Square would look like in an alternate universe wherein Disney still took over but retained the existing businesses/working people and just kind of spruced it all up. The staff keep it moving with a straight face and a light touch, which is...
The team behind Dear Irving and Raines Law Room opened the second outpost of the former in midtown. Dear Irving on Hudson is a bi-level cocktail bar that takes up the 40th and 41st floors of the Aliz Hotel in Times Square. While the bustling location is worlds away from the quiet block of Irving Place, the founders are sticking to some familiarities. Most noticeably, a handful of cocktails and a "time travel" theme, with one floor akin to 1960s James Bond and another decked out in Art Deco finishes.
The vibe: It feels like a rooftop lounge on top of a schmancy hotel in Times Square, which isn’t a bad thing–it’s just that everything feels highly curated because it is. Different corners each have their own vibe ranging from 70s living room to retrofuturistic afterparty.Â
The food: The menu is eclectic–lobster guacamole next to steak au poivre next to spiced nuts. All of it tastes nice but none of it stands especially proud.
The drink: There’s a small selection of beers and some wines, but this place is all about cocktailing. There’s a big variety on the menu, such as a smokey, spicy Xantolo featuring reposado, mezcal, and spiced pineapple.Time Out tip: The place was designed for you and a date to locate the perfect nook.
The Art Deco-styled bar and restaurant evokes a bygone era with touches like antique smoked mirrors, intage murals of burlesque dancers and a ceiling covered in Chesterfield-inspired cushions. Some drinks also skew to theme, with recipes from Prohibiton and an entire menu page focused on European-style gin-and-tonic service. If you're more thoroughly mordern, try the signature cocktails made with ingredients like coffee-pecan bitters and tomatillo-infused mescal.
The vibe: It almost feels like a beautiful Parisian train concourse bathed in golden light. Downstairs is duskier, tres cool millennial
The food: Sort of a gastropub brasserie hodgepodge upstairs. An assemblage of snacks downstairs with some asian inspired dishes.
The drink: Upstairs can handle any classic cocktail with aplomb, but they specialize in a variety of Gin and Tonics. Downstairs the drinks are whackier and more nouveau, like the Nighthawk cocktail featuring brown butter, Cynar, and coffee whiskey.
Time Out tip: Choose your own adventure, but doing dinner upstairs and then continuing with drinks downstairs feels right.
Only incidentally one of NYC’s latest speakeasy concepts, Nothing Really Matters aims only to be “the best cocktail bar in the universe,” rather than a late-arriving throwback. But it still fits the bill better than many of its contemporaries by virtue of its recessed entrance in a midtown subway station alone. Find your way downtown-bound to see whether the style tracks.Â
The vibe: Vaporwave. The decor is like a piece of polished obsidian; dark but glistening in all the glowing neon. The back bar looks like a crystal altar.Â
The food: Chips, nuts, popcorn, olives, and caviar with crem fraiche if you feel like taking that plunge. Pizzas are available to order to the bar Tuesday - Saturday 5pm-11:40pm, but there’s no kitchen.
The drink: There’s a few wines and beers, but the name of the game here is inventive, fun, seasonal cocktailing so the menu could be completely different depending on when you read this.Â
Time Out tip: If it’s busy, don’t ask the bartender to decide which cocktail you should drink–they’re there to make a living, not to please you, so be a grownup and make a decision on your own. If it’s slow, call a liquor and let the bartender do what they do. If you don’t feel like rolling the dice, try Cyllan’s Rum Punch–rum, pineapple, mango, passionfruit–it can get you in some trouble but, if you’re worried, refer to the bar’s name.
With Julien Levy
The vibe: Upstairs, the Ragtrader feels like it was conceived as a shooting location for Mad Men’s 2020s-set spiritual sequel. Downstairs, Bo Peep is red velvety, dusky, jazzy.
The food: Ragtrader’s food is a sort of gastropub/brasserie; pizzas, steak, dinner salads, etc. Bo Peep’s menu is shorter–mostly finger food (sliders, fried calamari, wings, etc.) and a few small plates in addition to pizza.
The drink: Ragtrader has a varied selection of tap beers, bottles and cans, wines by bottle or glass, and cocktails that are less inventive than iterative but still tasty and skillfully crafted. The Made in Midtown reminds us of a Sidecar with whiskey, citrus, and blackberry–sweet/tart sipper. Bo Peep’s beer and wine selection is smaller than upstairs, but the cocktail program is more imaginative and whimsical. The Sleepy Hollow is cinnamon mezcal, pumpkin, and ginger beer–slightly unhinged, fun, and super tasty; sort of like drinking a smokey, boozy jack-o-lantern.
Time Out tip: You can more or less walk into Ragtrader whenever and find a seat–it’s huge. That is a double edges sword though as the din is noticeable. Downstairs almost certainly requires a reservation for one of the two nightly seatings: 5:30pm or 8pm. Â
The 25th-floor rooftop bar in midtown is dedicated to Elsie de Wolfe, the 20th-century actress, socialite and interior decorator. The team behind the Refinery Hotel decked out the indoor/outdoor space in a glam aesthic of 18th-century French style. Chef David Burke created a menu of elevated American plates, while the cocktails are named after Elsie's tony life (The Windsor, The Colony Club).
Sunn's is a slip of a wine bar bordered on the cusp of Chinatown and Dimes Square. But it is more than enough space for Sunny Lee to make something special. Following her successful pop-up, Banchan by Sunny, Lee has moved operations out of her apartment and into a 16-seat spot in Chinatown. Inside keeps it quaint with blonde woods, a brick wall and back wall that almost mimics stitched leather. The space is billed as "a little place for banchan and wine" and it does that so, so well as little bowls of banchan feature rotating kimchi and chewy and sweetened candied squid that is one of the best bites of the bunch. The tteokbokki—one that you've likely seen on TikTok and the gram—is as is good as it looks with sweet tomato, a savory hit of gochujang and butter and a layer of stracciatella for all the pulling. Of course, there is good wine and spirits to be had here, all curated by neighboring bar, Parcelle Wine.  Â
The vibe: Things are laid-back and casual here and servers are more than happy to walk you through wine and banchan specials of the evening. Seats are a bit tight, so be ready to say hello to your neighbors if you need to use the bathroom.Â
The food:Â Favorites from Lee's pop-up days make the final menu, as do a number of new dishes, like the aforementioned tteokbokki. The banchan ($24) are just as amazing, the candied squid being one of the top.Â
The drink: Parcelle curates the wine list here, with bottles that span the globe along with Korean lagers, Hana...
At this 54th-floor bar that almost brushes the sky, expect an impressively extensive drinks menu where innovative and classic cocktails take center stage. In fact, the cocktail menu is split into several themed sections, including spiced and shaken, stirred and spirit-forward, bubbles and fizzes, winter in the tropics and more. If you’d rather not partake in the cocktails, Bar 54 also offers beer, wine and spirits with mixers.
The bar food menu is concise and includes snacks (olives, nuts), plates for one (burgers, flatbreads) and dishes to share (cheeseboards). Views run from sky to sea and the 1,400-square-foot terrace is outfitted with wood-paneled walls, leather banquettes and outdoor fireplaces.Â
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Smack in the middle of Times Square—two blocks from Madison Square Garden and perfectly perched with panoramic skyline views—Vue 180 is a rooftop bar that brings elevated energy to the heart of NYC. True to its name, the turf-furnished terrace offers sweeping, 180-degree views that include Hudson Yards and the iconic Empire State Building.
You can soak it in year-round thanks to a climate-controlled indoor lounge that connects seamlessly to the outdoor space, complete with high-end seating, flat-screen TVs and winter-ready perks like space heaters and cozy igloos.
Free entry for guests 21+ keeps the vibe accessible, while live music on select nights and ticketed open-bar events add a little extra buzz. The food and drink menu comes courtesy of a Manhattan-based chef, which means elevated cocktails and light bites that actually hold their own against the view.
Planning a big night? The rooftop can be reserved for private events, from polished corporate mixers to just-because-it’s-NYC celebrations. Expect customizable spaces, cocktail and beer towers, top-tier AV setups and all the skyline you can handle.
And if you’re not ready to call it a night, don’t. The DoubleTree Times Square South sits just downstairs, making it wildly easy to transition from rooftop party to hotel suite to bottomless mimosa brunch in one elevator ride.
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Been there, done that? Think again, my friend.
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