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What to Do in New York City in May 2023

By Emmie MurphyApr 20 2023
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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 also chock-full of things to do and see this time of year. Artist Paula Crown’s two-part exhibition project is on through May 21, and rollerskating at Flipper’s has returned for another year.

From a citywide bike tour to world-class performances, here's what to do in New York City in May.

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Courtesy of TD Five Boro Bike Tour
Courtesy of TD Five Boro Bike Tour

1. TD Five Boro Bike Tour

May 7

Wide-open city streets with no cars? It must be a pipe dream, right? Wrong. On May 7, 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.

Photo by J. Grassa for Westminster Kennel Club
Photo by J. Grassa for Westminster Kennel Club

2. Westminster Kennel Club Dog Show

May 6-9

While “the second-longest, continuously held sporting event in the US” may conjure up thoughts of runs batted in or touchdowns scored, it actually means wagging tails and obedience contests. From May 6 through 9, NYC will host the crème de la crème of the canine world at the USTA Billie Jean King National Tennis Center for the Westminster Kennel Club Dog Show. Across several days, thousands of champion dogs will put their best paws forward to compete for the coveted “Best in Show.” Grab your tickets here.

“Le Moulin Rouge de la Galette,” 1900; courtesy of the Guggenheim
“Le Moulin Rouge de la Galette,” 1900; courtesy of the Guggenheim

3. Young Picassso in Paris

Beginning May 12

In conjunction with celebrations across the globe that commemorate the 50th anniversary of Picasso’s death, the Guggenheim exhibition Young Picasso in Paris explores the artist’s introduction to the city that would become his permanent home. Beginning with an early representation of the famous dance hall from 1900, Le Moulin de la Galette, the exhibition continues to trace the development of the Spaniard’s artistic voice. Across paintings and works on paper, the exhibition takes visitors through a pivotal year of Picasso’s life and showcases the early experimentation that would come to define his oeuvre.

4. The Today Show Summer Concert Series

Beginning May 12

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 will kick off with a performance by the Jonas Brothers on May 12, and future performers will be announced here. Better yet? These events are completely free, but be sure to arrive early to secure your spot.

Photo by Andres Orozco; courtesy of NYCxDesign
Photo by Andres Orozco; courtesy of NYCxDesign

5. NYCxDesign Festival

May 18-25

Back for its 11th year, the NYCxDesign Festival will present exhibitions, installations, studio tours, talks, and more from May 18 to 25. Celebrating New York City as a global center of design excellence, the festival spotlights the designers, makers, and manufacturers. Welcoming thousands of visitors each year for programming throughout all five boroughs, the festival showcases the power of design and its essential role in our city.

Courtesy of Radio City Music Hall
Courtesy of Radio City Music Hall

6. Barry Manilow at Radio City Music Hall

Starts May 31

Grammy, Tony, and Emmy-winning pop artist Barry Manilow returns to his native New York to take the Radio City stage for a limited five-night engagement, marking his 35-39th lifetime performances at the venue. One of the most successful adult contemporary singers of all time, Manilow has sold over 85 million albums, headlined thousands of concerts, and boasts 28 platinum records. Tickets for all five shows are on sale here. Plus, Radio City is right at Rockefeller Center, so enjoy the show, then come have a bite to eat and get a view of the skyline from Top of the Rock.

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