What to Do in New York City in May 2022

By Emmie MurphyApr 21 2022

Beach reopenings, rising temperatures, and bright blooms all signal a new chapter ahead. The harbinger of summer, May is a month to revel in New York at its best. Long gone are the short, dark days, and it’s time to soak up the spring and all that the five boroughs have to offer. Rockefeller Center is always chock-full of things to do and see, so be sure to explore the full list of events; this month, Hugo McCloud’s Art in Focus exhibition is on display around the campus.

From a rooftop vineyard with views to world-class performances, here's what to do in New York City in May.

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New York City May Events

1. The Today Show Summer Concert Series

Throughout the month of May

One of the iconic signs of summer in the city is the return of outdoor concerts hosted by The Today Show. The Summer Concert Series brings weekly live performances outside the show’s studios at Rockefeller Center. The concert series begins in May and runs through early September, presenting singers of all stripes to the Midtown plaza. This year’s lineup has yet to be announced, but eager concertgoers can keep an eye on the concert series site for forthcoming details. Better yet? These events are completely free, but be sure to arrive early to secure your spot.

Man rides his bike past Radio City Music Hall during the TD Boro Bike Tour

Photo courtesy of TD Five Boro Bike Tour

2. TD Five Boro Bike Tour

May 1

Wide-open city streets with no cars? It must be a pipe dream, right? Wrong. On May 1, the TD Five Boro Bike Tour will deliver just that. Riders will have full access to 40 miles of open roads and traffic-free bridges as they bike throughout the five boroughs. Not just a fun activity, the bike tour is primarily a fundraising event and one of the world's largest charitable bike rides. Funds go toward bike education and safety programs and the event also partners with dozens of nonprofits to raise money for causes that range from cancer research to social services organizations. Cheer riders on, and check out this map to see where they’ll be passing through.

3. Matisse: The Red Studio at MoMA

May 1 - September 10

Step into Henri Matisse’s studio at MoMA’s newest exhibition. In Matisse: The Red Studio, which opens on May 1, the Museum of Modern Art will reunite The Red Studio with six paintings, three sculptures, and a ceramic piece that are depicted in the famous painting. The grand 6-by-7-foot canvas portrays Matisse’s studio in the Parisian suburb of Issy-le-Moulineaux. In it, the artist represents works of varying renown, and the exhibition is the first time these will be reunited since the artist’s death. This reunion, paired with photographs and archival material, presents an unparalleled opportunity to not only appreciate the depth and breadth of Matisse’s oeuvre, but to also gain insights into his working environment and artistic process.

Plus, MoMa is only a few blocks from Rockefeller Center, so enjoy the exhibition, then come have a bite to eat and get a view of the sunset from Top of the Rock.

New York City Ballet in George Balanchine’s Firebird

Photo by Erin Baiano, courtesy of the New York City Ballet

4. New York City Ballet’s Stravinsky Festival

May 3 - May 15

During the first few weeks of May, lovers of music and dance will be treated to New York City Ballet’s Stravinsky Festival. The festival includes four different programs that explore the breadth of composer Igor Stravinsky’s career as well as the engaging variety of NYCB’s repertory. The various programs feature works by George Balanchine, Jerome Robbins, and NYCB Resident Choreographer Justin Peck, as well as a new ballet by former NYCB dancer Silas Farley. Beyond the dancing and the music, the performances will showcase costumes that range from the minimalism of Balanchine’s black and white ballets to the surrealist whimsy of Tsumori Chisato’s designs for Peck’s Pulcinella Variations. It promises a marriage of multiple art forms and reminds us all at once of the famed history of the company alongside its continued evolution.

Photo courtesy of Rooftop Reds

5. Pizza, Wine, Movie Nights at Rooftop Reds

Throughout the month of May

Wine grown on a Brooklyn rooftop is intriguing enough, but pair that with sprawling city views, brick oven pizza, and an epic throwback movie, and it’s impossible not to love Rooftop Reds at Brooklyn Navy Yard. Rooftop Reds happens to be the only vineyard in Brooklyn, and the only rooftop winery in the entire city. Every Thursday from May through October, they host “Pizza, Wine, Movie Nights” where guests can watch a classic film, play some cornhole, drink some wine, and enjoy a totally unique experience. On May 19, cinephiles and oenophiles alike can purchase tickets to Hook, and on May 26, the winery will screen Selena. Tickets include two slices of pizza and popcorn.