Wood-Grilled Pizza: Pizza or Flatbread?
Overpaying for a drink is kind of a bummer when the temperature drops below 70. While you’re still jacket-free, the views at Westlight atop the William Vale Hotel are worth the elevated bar tab. Snag a seat on the wrap-around deck (or in the pop-up standing area, Turf Club) for spritzes and upscale bar snacks. Snap a few selfies with the skyline just before sunset, and then head down to the lower patio for hot honey-covered chicken fingers and swirls of soft serve at Mister Dips.
This new Aztec goddess-inspired upscale Mexican restaurant by Speedy Romeo’s Justin Bazdarich serves bomb guacamole and frozen margaritas on a patio separated from the busy sidewalk by a thin, hip-height strip of greenery. Dog-friendly and perfect for people watching, the space can accommodate date night, or larger groups. Ambient noise is low enough to enjoy a conversation.
The telegenic, French-inspired, New Orleans-esque neo-bistro (tldr; Instagram-friendly eatery) across from McCarren Park has one of the best sidewalk cafes in the neighborhood, uncomfortable date with your mom and her ex-boyfriend or not. Yes, they take brunch reservations.
2018 will go down in history books as the year NYC finally got a rooftop bar worth going to Midtown for. This 1920s-era art deco panoramic balcony on the 26th floor of the Beekman Tower got a chic upgrade this year, allowing you to sip craft cocktails (think Buffalo Trace bourbon and watermelon juice) and eat avocado toast on a historic and legitimately cool rooftop terrace.
This cocktail and seafood restaurant by the Grand Banks team requires a short ferry ride to Governors Island, but the views, and booze, are worth it. Island Oyster is only open during the warmer months, when wine, beer and tiki cocktails are pair with oysters, lobster rolls and incredibly views of the Manhattan skyline.
Brooklyn Navy Yard
Hidden in plain sight in the Brooklyn Navy Yard, Rooftop Reds is currently New York City’s only commercial urban vineyard and winery, meaning they produce wines from grapes grown on their rooftop (supplemented by Finger Lakes vineyards). Visits are reservation-only, so book a spot online, take advantage of the BYO food policy, and spend one of your last warm weather sunsets atop this unlikely vineyard.
This barbecue joint’s sprawling outdoor patio stays open until it’s too cold to sit outside (in which case, you can slide into the adjacent indoor space). Enjoy the last of the lingering warm weather at a wooden picnic table with baby back ribs, brisket, and frozé. Then wipe the brown sugar and sticky honey glaze off your fingers and play a round of cornhole.
The cocktails at Dale Talde’s bar on the 21st floor of Hotel 50 Bowery are inspired by the neighborhood. The Crown Manhattan incorporates szechuan tincture, and the Black Dragon Tea mixes vodka with oolong tea, green tea, and spiced kalamansi. You’d normally have to leave the borough for skyline views as sweeping at these.
Pier 6, Brooklyn Bridge Park
This Grand Banks spinoff welcomes waterfront drinkers into its nautical space housed on the deck an old ship. Navy-blue stools surround a U-shaped bar, big yellow-and-white striped umbrellas provide shade, and the lower Manhattan skyline glitters across the river. Pair East Coast oysters with a Seabrind Martini -- gin, vermouth, Cocchi bianco, and Champagne mignonette.
Take one last trip out to the Bronx’s hidden fishing village to hit the large waterfront seating area at this cafeteria-style, fried seafood joint. Load up on deep fried shrimp, lobster chunks, and calamari; grab a $6 frozen daiquiri; and sit at one of the many shareable metal picnic benches looking out over the Long Island Sound.
That outdoor bar your friend who moved to Ridgewood disappeared to all summer? Nowadays. From the team behind the Mister Sunday dance parties, this massive backyard hosts a never-ending celebration -- complete with live music, ping-pong, and cheap drinks (beer starts at $5, and two-for-one happy hour runs until 8pm on weekdays) -- that may make you long for a few more unbearably sticky summer nights, just so you can hang out here a little longer.
Chef Missy Robbins’ sensational pasta restaurant is nearly impossible to get into, but a sizable outdoor seating area open to walk-ins makes trying the legendary malfadini far more feasible. If you do have to wait, grab a seat in the public, Wi-Fi-equipped park across the street.
One of the best square slices in New York is procured from a window at this old-school South Brooklyn red-sauce joint. Bring a crew to order a whole square pie (the fluffy crust is deceivingly light) and pick a spot at one of the outdoor metal benches.
Though this Crown Heights bar has ample indoor space, the outdoor picnic benches and beer garden are the best reason to hang out here. Grab a draft beer or a boozy milkshake and some chili cheese fries and spread out at one of the many outdoor tables before they’re covered in snow.
Perhaps better known as “that restaurant near The Cloisters,” this far-uptown eatery looks more like a lakeside restaurant in a quiet Connecticut vacation town than a city establishment just north of Fort Tryon Park. Located on The Hudson, the outdoor patio is appointed with outdoor couches, loungers, and group tables where you can sip on a cocktail and eat seafood-inspired dishes like fried shrimp, clams, or a whole steamed lobster.
Just one step away from drinking on an actual boat, the anchored-down Brooklyn Barge lets you imbibe outside without the seasickness. Completely outdoors, this festive barge offers plenty of communal tables and open space, all illuminated by party lights and skyscrapers across the East River at night. Go for the $8 glasses of Long Island wine on tap and $24 pitches of draft beer.
This international Italian mini-chain opened its first New York outpost this summer, claiming one of the best views in Dumbo, if not all of New York. Skip the stylish interior for a wicker seat on the shaded patio, where you can feast on a wide range of pasta, risotto, wood-fired proteins, and pizzas all day long.
If you don’t know about the quaint and impressively quiet backyard hidden behind this tiny French bakery, make it your mission to check it out before the door locks for the season. Grab a seat at the communal farm table or one a few two-seaters, sip an iced matcha, eat a pastry, read a book, and enjoy the much-needed Downtown respite.
If eating pasta at a sidewalk cafe is your thing, look no further than Bar Pitti, the legendary celebrity hangout known for simple Italian food. While you might not catch Kendall Jenner twirling spaghetti in the dining room, the cluster of sidewalk tables on Sixth Avenue are prime for people-watching (and penne alla vodka-eating).
This quaint Italian joint in the West Village, co-owned by powerhouses Jody Williams (Buvette) and Rita Sodi (I Sodi), always has a substantial wait, thanks to its no-reservations policy. While the list of names on the wall (literally, the waitlist is chalked on the entry wall every night) is no shorter in the summer, the addition of romantic two-seater tables on Grove Street makes the hour-plus wait progress a little faster -- plus, you can sneak in some people-watching before indulging in homemade pasta and veggie-focused sides.
Should you find yourself in the mood to ogle New Yorkers’ yachts and slightly less-enviable sailboats, grab an outdoor seat at Boat Basin, a cafe and bar on the west end of Riverside Park, adjacent to the Hudson River boat parking lot you probably didn’t know existed. The menu is basic here (avocado toast, hot dogs, big salads) but you’re really here for the views and the unobstructed breeze, best enjoyed over a shared pitcher of strawberry margaritas or a bucket of Coronas.
South Street Seaport
Summer is pretty much the only season when it’s worth visiting the South Street Seaport, so head down to the lowest tip of Manhattan before the cooler weather hits. Industry Kitchen boasts an impressively large dockside patio, so you can people-watch and boat-watch outdoors while picking through a pot of mussels and sipping a Summer House -- vodka, St. Germain, lemon, strawberry, Prosecco.
Upper West Side
Dim sum outdoors is a rarity in New York, so be sure to take advantage of the patio dining at the Upper West Side offshoot of this popular Chinatown behemoth. The menu offers all the same dumpling and noodle dishes you can get Downtown, in addition to a craft cocktail list full of Chinese-inspired ingredients.
The Millennial pink paradise inside this new fast-casual pasta spot from By Chloe’s Samantha Wasser is a cozy go-to lunch destination come winter, but while your puffy jacket is still packed away, eat your bucatini arrabiata at one of the restaurant’s outdoor tables.