NYC events in May 2025

In the four years since it opened, Little Island has become one of New York's primo warm-weather destinations: an elevated oasis of trees and knolls and winding paths that rises—as though suspended on a bed of coupe cocktail glasses—above Pier 55 in the Hudson, just west of the Meatpacking District. In the same brief period, it has established itself as one of the city's most vital sources of low-cost high culture in the summer. 

Concerts, plays, dance shows, operas: These and more can be found on Little Island all summer long, whether at its 687-seat open-air amphitheater (the Amph), its smaller performance stage (the Glade) or at pop-up locations throughout the space. Performances have been part of Little Island's mission from the start, but the offerings have gotten more and more ambitious. Last year, the park upped its game to present a sold-out season of world premieres.

Building on that success, Little Island's 2025 season includes many new works by major artists. Many of the shows are free, and those that aren't cost just $25; to buy tickets to them, visit Little Island's ticketing page on TodayTix.  

Hitting a Yankees game couldn’t be more quintessentially New York. The Major League Baseball team, which won the World Series in 1978, 1996, 1998, 1999, 2000 and 2009, made it to the World Series again in 2024! To date, the Yankees have won 27 World Series in 42 appearances, the most in the MLB in addition to major North American professional sports leagues. Through 2024, their all-time regular season winning percentage is .569 (a 10,778 – 8,148 record)—the best of any team in MLB history.

Grab your tickets now to see NYC in action!

Rooftop Cinema Club takes movie-going to a whole new level—literally. This rooftop film series at a midtown skyscraper offers stunning views and an impressive lineup of films. 

In addition to the movie magic, the venue also offers movie snacks, a full bar and cute photo opps. This season features movies that will appeal to ‘90s kids, a Grease sing-along, Pride films, Wine Wednesdays and lots more when the 2025 calendar opens in May. Here’s the full list of what’s coming to Rooftop Cinema Club’s big screen.

Sometimes you want to soar above it all, sipping effervescent libations among the clouds like some kind of fancy bird with an expense account. You want to be uplifted. 

In the city that never stops sprawling, upward expansion has also reached great heights. Many incredible eating and drinking destinations are poised in the sky like treehouses with cover charges. Among these rooftop bars are old New York throwbacks, party destinations and seaside terraces practically fashioned for Instagram. They each offer booze, some kind of view and an invitation for you to get high. Keep reading for our favorites.

Smorgasburg, the food bazaar spectacular, is back with dozens of great local vendors across three locations. Smorgasburg WTC runs on Fridays; Williamsburg is on Saturdays; and Prospect Park is on Sundays. Each location is open weekly through October. 

For its 15th year of outdoor food and fun, Smorgasburg will showcase more than 70 vendors. The food festival will be filled with fragrant Ethiopian stews, Hawaii-style street comforts, explosive pani puri, potato puff poutine and lots more.

Need a laugh? The Second City—the renowned comedy club with locations in Chicago and Toronto—is now open in Brooklyn, and you will definitely laugh out loud there. 

Some of the funniest names in comedy got their start at Second City. Just a few Second City alumni include: Bill Murray, Eugene Levy, Catherine O'Hara, Amber Ruffin, Keegan-Michael Key, Chris Farley, Tina Fey, Stephen Colbert, and Aidy Bryant. You might just see the next comedy star on this stage.

The venue offers sketch shows and improv performances, along with a great restaurant and no drink minimums in a beautiful venue. Tickets start at $39.

Ahoy, sailors! Fleet Week NYC is a celebration in New York City honoring the members of the United States Navy, Coast Guard and Marine Corps. From May 21-27, the weeklong party includes discussions, ship tours, performances and military fun.

Every year on Memorial Day, NYC kicks off the start to summer with tons of events. Memorial Day isn’t just about day-drinking and savoring the long weekend—it’s also about honoring the men and women who have died while serving in our armed forces.

So before you chow down on the best BBQ in the city and line up for the best Memorial Day sample sales, remember the sacrifices made for the red, white and blue.

At last, night market season has arrived. A bevy of open-air night markets will pop up around town this summer, from the upper reaches of the Bronx to Queens. We've rounded up details on all of them, so grab some cash and make plans to eat locally—and deliciously. 

Grab your paddles, pickleball fans, because the popular sport is back in Central Park all spring and summer long. CityPickle is now open at the park's Wollman Rink through the early fall. 

This is the fourth season for pickleball on 14 courts in the center of Manhattan—the largest pickleball offering in the Northeast. This tennis/ping-pong/badminton hybrid has become the country's fastest-growing sport, with more than 130,000 New Yorkers flocking to Wollman Rink's courts in past years. All skill levels are welcome for court rentals, clinics, open play, and private events from 8am to 9pm daily. Plus, expect summer camps, events, and special free programming. 

Revel in warmer weather at the annual Macy’s Flower Show. NYC will be budding with blooms all over, but nothing beats roaming the sweet-smelling foliage that suddenly appears at one of the city’s best department stores: Macy’s Herald Square.

This year's theme hasn't been announced yet, but Macy's says the show will transform the store's main floor, balcony and windows. Expect "a whimsical oasis featuring the beauty and fragrance of spring as thousands of plants, flowers and trees bloom on the iconic store's main floor," Macy's officials said in a press release.

The Flower Show runs is on view through May 18.

You can do better than a dozen carnations for Mother’s Day (Sunday, May 11) this year to show Mom how much you love her and how well you know her.

After all, she brought you into the world, so the least you can do is show your appreciation. Check out this list of things to do on Mother’s Day including the best restaurants in NYC to take her to, the best shops in NYC for gifts, spas in NYC for a relaxing day, flower shops for the perfect bouquet—basically, how to spoil the most important lady you know.