Top 10 Things To Do In May

My Art Fair Lady
The Frieze Art Fair takes over Randall’s Island

Nowhere on earth is more beautiful than New York in May (ask any New Yorker; they’ll proudly tell you!), and the only way to amplify the region’s natural splendor is by adding art. Enter Frieze Art Fair, a weekend-long outdoor installation featuring talks, site-specific commissions, and food from top NYC restaurant vendors. From 5/5-5/8, meander over the 103rd St. Pedestrian Bridge or snag a Water Taxi to Randall’s Island. Our favorite way to visit? Friday after work, when tickets are just $29 per person from 5 p.m. until 8 p.m. (Randall’s Island Park)

Root, Root, Root for the Home Team
The greatest rivalry in sports comes back to the Bronx

Sure, the Boston Red Sox didn’t exactly mount a championship-caliber season in 2015, finishing dead last in the AL East. But that was music to Yankee fans’ ears! From 5/6-5/8, the Bronx Bombers will do their damnedest to deal three more losses to their hated northern rivals, playing a weekend series that pits former Fenway phenom Jacoby Ellsbury and the game’s best-paid designated hitter, Alex Rodriguez, against Dustin Pedroia and his band of bearded houligans. May the best man win. (Pro Tip: if you’re in New York, the Yankees are the best men.) (1 E. 161st St.)


Two [Hulls] if by Sea
America’s Cup races into New York Harbor

New York’s skyscrapers are a sight to behold, but this spring, the city’s legendary horizon gets a new (temporary) addition: the soaring sails of catamarans in the Louis Vuitton America’s Cup World Series. On 5/7 and 5/8, the light-as-air boats will compete in the lower Hudson River, earning points in the years-long cup and creating a seaside spectacle unlike any other. Spectators’ HQ will be Brookfield Place’s Waterfront Plaza, with entertainment, food vendors, a kids’ zone, live music, and large screens showing the race – which will also be seen live on the water just offshore. (230 Vesey St.)

Behold the Golden Age
Cirque du Soleil comes to The Great White Way

Bridging theater and spectacle, Paramour is a one-of-a-kind performance piece from the wizards of Cirque du Soleil. Opening on 5/25 at the massive Lyric Theatre on 42nd Street, Paramour is a departure for the acrobatic company, and bridges their soaring, circus-inspired style with the emotional resonance and musical grandeur of a classic Broadway musical. Set in Hollywood’s golden age, it follows the story of a poet forced to make a difficult choice – presumably between, say, love and art, not whether or not to fly through the air with the greatest of ease (she will). (213 W. 42nd St.)

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Harlem EatUp

EatUp, Uptown
Harlem EatUp! is back for 2016

Following a successful first year, honorary chair Bill Clinton and co-chairs Marcus Samuelsson and Herb Karlitz are back with their second-annual Harlem EatUp! This three-day, food-focused fest celebrates the neighborhood’s unrivaled culinary heritage and bright future with a Friday night dinner series, plus weekend walk-around tastings in Morningside Park and a family-friendly food market that will also showcase interactive activities and local artists. There’s no better way to get a taste of the New Harlem Renaissance – especially with food from famed Sylvia’s, Red Rooster, Dinosaur Bar-B-Que, and more. (

Belly Laughs
Happy, Joe, Terry, and Deuce walk into a theater…

This is not a joke: Netflix’s Do Over Tour is coming to Brooklyn, and the line-up is a comedy wrecking ball: Adam Sandler, David Spade, Nick Swardson, and Rob Schneider. On stage. Together. At Kings Theater. Between them, these guys have a roster of cult movies and hilarious TV shows that you’ve been laughing at for more than two decades, including some of SNL’s most memorable skits. There’s no telling what will happen when they all get together back in New York; all we know is, you won’t want to miss it. So go on: tell us you have other plans on 5/25. We know you’re just joking. (1027 Flatbush Ave. at Tilden Ave.)

Artful Storytelling
Roz Chast: Cartoon Memoirs exhibits at the Museum of the City of New York

Brooklyn’s own Roz Chast has delighted comic fans for more than 40 years, contributing to The New Yorker and illustrating a hilarious visual memoir, Can’t We Talk About Something More Pleasant? In this showcase of her career, fans and first-timers alike will be delighted with more than 200 works that find humor in the absurdities of daily life. Her involving cast of recurring cartoon characters progress through self-doubt to find joy in the simplest experiences, and it’s impossible not to smile along with them, courtesy of Chast’s boldly drawn vision of the world through her eyes. (1220 Fifth Ave.)

Maritime Marvels
Footloose and Fancy Fleet Week

Beginning on Wednesday 5/25, climb aboard! New York’s annual Fleet Week washes ashore, with daily tours of the ships docked along the city’s Hudson River waterfront, plus a veritable invasion of sailors, all in town for the holiday weekend. Parades are mostly on Sunday and Monday, with festive happenings in all five boroughs and along the Jersey coast, but we’re partial to the General Public Ship Tours, held daily from 10 a.m. until 5 p.m. from the Intrepid Sea, Air & Space Museum at 46th Street and the river. (W. 46th St. at 12th Ave.)


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The Pavilion

Make It a Tall One
Sip the skyline at The Pavilion

These streets will make you feel brand new – big lights will inspire you, cold drinks will revive you. Each spring, Union Square’s The Pavilion comes to life, offering open-air cocktails and snacks in the heart of lower Manhattan. It’s your chance to truly “drink in” the skyline: sample Coney Island Mermaid Pilsner on draught, or pour out a 6 Train, citron vodka with cucumber, honey-thyme syrup, and soda. New York has famously inspired artists (and drinkers) of all genres for centuries, so slurp an elixir and see if the city that never sleeps can revive you, too. (20 Union Square West)

See Forever
One World turns one

On 5/29, one of New York’s newest landmarks hits a milestone: One World Observatory at One World Trade Center turns one year old. Celebrate with a trip to the top of the tallest building in the Western Hemisphere, where the entire city splays out beneath you like a technicolor map of Manhattan and beyond. To really get into the celebratory spirit, raise a glass of sparkling at sky-high bar One Mix, then stand on the real-time video platform that makes you feel suspended over the bustling city streets below. (285 Fulton St.)