NYC 2020 May Activities, Things to Do and Events Calendar

New York City Events May 2020 include Billy Joel in concert, Ninth Avenue Food Festival, Fleet Week, Memorial Day, Mother’s Day, Washington Square Outdoor Art Exhibit, Five Boro Bike Tour and so much more. Sarah Jessica Parker and Matthew Broderick star on Broadway, alongside Mrs. Doubtfire, The Lehman Trilogy, Diana and Six.

The weather in NYC in May is delightful and the Central Park foliage is fully blooming, making one of their free tours an ideal thing to do in May. Check our calendar for Things to do in NYC in May, NYC Events May 2020, Shows in NYC in May, events in NYC tonight, NYC events this weekend and more New York City upcoming events.

Memorial Day Weekend is officially the start of the summer, so expect New York City to clear out on May 22nd for the whole weekend. Please check sightseeing hours for Memorial Day, Monday, May 25, 2020 and be sure to treat Mom on Sunday, May 10th.

Add your event to the New York City Events Activities May calendar.

Top NYC May Events

  • Shakespeare in the Park
  • Mothers Day in New York City
  • Billy Joel @ MSG
  • The Met Roof Garden & Martini Bar
  • Ninth Avenue Food Festival
  • Taste of Tribeca
  • Yankees & Mets Baseball
  • Memorial Day Weekend NYC
  • Fleet Week New York City
  • Five Boro Bike Tour
  • GMA Summer Concert Series
  • TODAY Show Summer Concert Series

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NYC Custom Travel Planning by NYC Insider Guide

Ready for your very own NYC Insider working just on your trip? Want a "Plan My Vacation for Me" service and your own personal NYC concierge? Let me help you with exactly what you want to know to make the absolute most of your NYC Vacation. More Info: Customized New York Travel Planning and Itineraries for the best events, show tickets, hotels, shopping, restaurants and more.

New York Travel Planning

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Concerts NYC May Shows, Events, Things to Do

May New York City Concerts Shows

See All: NYC Concerts Shows May – includes Good Morning America Summer Concert Series, Today Show Summer Concert Series, Jones Beach, Central Park Summerstage, Coney Island, Forest Hills and more.

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New Hotels in Manhattan

New hotels in Manhattan give you access to crisp sheets, new linens, towels, restaurants, rooftops and more before anyone else gets to them. While you may have to deal with some grand opening kinks, you'll often get amazing rates at the newest Manhattan hotels before the full buzz is out there for everyone to discover. Recently opened hotels include:

New Hotels in Manhattan

See All: New Hotels in Manhattan

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Sports New York City Events May 2020

May is a great sports month in NYC! Baseball and Football Club seasons are well under way and, hopefully, we have a basketball or hockey team in the Playoffs. The sports atmosphere in New York is exhilarating year round and some of the most intense competition is within our own rivalries.

If the Rangers or Islanders are in the the playoffs, schedules will be posted here. Make sure to add a NYC Game Day to your NYC vacation – it’s an absolute MUST in NYC!

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Mothers Day in New York City

Mother’s Day in New York City offers a ton of choices for every budget and interest.

Mothers Day in New York City

Choose from special Brunches and Dinners, Broadway shows, free cocktails and open bars, tons of special Manhattan Cruises, chocolate tours, baseball, Broadway, private movie screenings and so much more.

More Info: Mothers Day in New York City

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NYC Insider Print Map and Guide to Manhattan

Download over 100 pages of NYC maps, information and recommendations in less than 5 minutes! Our NYC Insider Printable Map Guide Book, Travel Planner and Bonus Map Guides include organized, easy to follow, color coded guides, detailed maps of every neighborhood, weekly chart of Free Museum Days and Times and free weekly neighborhood tours, Best of NYC Categories and lists by ALL native New Yorkers. Download everything you need to know NYC Like a Pro and make the most of your NYC vacation.

NYC Printable Map Guide Book

The information provided is exactly what we were looking for to be able to plan our trip this year to NYC!! We are over the moon at all the information and maps we received. Our excitement has grown exponentially since we got our info. Thank you for the thoroughness of your guides! Well worth it! - Odette (March 2019)

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NYC Travel Vacation Advice

New York Travel Planning

Looking for personalized New York Travel Planning? Want a "Plan My Vacation for Me" Service? How about your own personal NYC Concierge, NYC Insider Guide, to help with exactly what you want to know? I can offer customized planning for the best events, show tickets, hotels, shopping, restaurants and more.

Classic New York City Tourist Attractions

See All: New York City Tourist Attractions

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May Things to do with Kids in New York

Things to do with Kids in New York

Festivals, Charlie and the Chocolate Factory, Baseball, Central Park, the Zoo and more. Great things to do with kids in May include:

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NYC Sightseeing Cruises - NYC Insider Guide Favorites!

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Memorial Day Weekend NYC

Memorial Day NYC

May 22-25, 2020

Memorial Day Weekend New York City offers a ton of choices for enjoying NYC and paying tribute to those who fought in our US Armed Forces. Free Museum Admission for Military Members, Fleet Week, FREE outdoor movies, Art Exhibits and much more!

Read More: Memorial Day Weekend NYC

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Best New York City Hotel Rooftops

NYC Hotel Rooftops offer some of the best skyline views in the whole City, along with cocktails and food, views, pools, cabanas, sundecks and retractable roofs. Our top picks for the most surreal views and cocktails include:

New York City Hotel Rooftops

See More: Best New York City Hotel Rooftops

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Shakespeare in the Park 2020

Shakespeare in the Park NYC

TBD 2020
May 21 – August 11, 2019
Delacorte Theater, Central Park

Every year, stars such as Meryl Streep, Al Pacino and James Earl Jones perform modern interpretations of various Shakespeare plays in Central Park at the 1,800 seat open-air theater and they are attended by over 80,000 people. 2019 Shakespeare in the Park plays are Much Ado About Nothing (May 21 – June 23) and Coriolanus (July 16 – August 11).

NYC Insider Guide knows just how you can get tickets. Learn More at Shakespeare in the Park 2020

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Central Park NY Hotels

These are NYC Insider hand picked hotels that are not just “near” Central Park, as most NYC hotels claim to be…but on the Park itself, either Central Park South, Central Park West or Fifth Ave. Many other hotels are nearby, or within a few blocks, but these are the closest, and all offer Park views from select rooms.

Central Park NY Hotels

Some of our top value picks near Central Park include:

See the Insider Guide for dozens more Central Park NY Hotels and download our free Central Park map at Central Park NY Guide

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Save with a New York City Attractions Pass

Get savings coupons and find the best New York City Discount Pass for your NYC vacation. Unbiased reviews of the New York City Sightseeing Passes. Which is the BEST – NY Sightseeing Pass, New York City Explorer Pass, New York Pass or New York CityPASS?

NY Sightseeing Pass
NYC Sightseeing Pass

  • Choose from 100 sights
  • Choose 1-10 days or # of Attractions
  • Unlimited Hop On Hop Off Bus
  • NY Sightseeing Pass

The New York Pass
New York City Pass Discounts

  • Includes 100 tours and attractions
  • Choose 1, 2, 3, 5, 7 or 10 Days
  • Digital or Physical Pass
  • New York Pass

Go New York Explorer
New York City Explorer Pass

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Broadway Shows NYC May 2020

Broadway has a TON of new shows and legends on stage.

Plaza Suite Comedy Play

Plaza Suite Comedy Play - Sarah Jessica Parker & Matthew Broderick, Play by Neil Simon

March 13-July 12, 2020 - Matthew Broderick and Sarah Jessica Parker return to Broadway together in this hilarious and piercing look at love and marriage by Neil Simon. The play is composed of three acts, in which Broderick and Parker play different couples, all set in Suite 719 of The Plaza Hotel. The first act is a long-wed couple revisiting their honeymoon suite, the second is a Hollywood producer and his old flame, while the third act is a married couple on their daughter's wedding day.

 

Mrs. Doubtfire Broadway Musical Tickets

Mrs. Doubtfire Broadway Musical Tickets

Helloooooooo! Mrs. Doubtfire is a musical now, poppets, and she's here to make everything better! Daniel Hillard, a struggling, out-of-work actor, will do anything for his kids. After losing custody in a messy divorce, he disguises himself as Scottish nanny Euphegenia Doubtfire in a desperate attempt to stay in their lives. As his new persona begins to take on a life of her own, Mrs. Doubtfire teaches Daniel more than he bargained for about how to be a father. Previews March 9, 2020. Ages ??+

The Lehman Trilogy Broadway Play

The Lehman Trilogy Broadway Play

Directed by Academy Award®, Tony® and Golden Globe® winner Sam Mendes, The Lehman Trilogy follows three brothers from their arrival in America in search of a new life, to the collapse of the firm they established, to the resulting financial crisis, the largest in history. The Wall Street Journal says, "You should crawl across broken glass to see it." NYC Insider Guide saw this in London and it was AMAZING! The acting is superb, the characters indelible and the set design totally unique. This is a true New Yorkers play and a must-see. Previews March 7, 2020

Diana Broadway Musical

Diana Broadway Musical - Previews: March 2, 2020

When Lady Diana Spencer married Prince Charles, she instantly became a cultural phenomenon. Leading fiercely with her heart, Princess Diana stood up for her family, her country and herself. She defied expectations, she rocked the royals and she created a legacy that will endure forever. DIANA is the electrifying new musical about a woman who chose to be fearless, and as a result became timeless.

Six the Musical Broadway

Six the Musical Broadway

Divorced, beheaded, died, divorced, beheaded, survived. Six centers on the six ex-wives of King Henry VIII, who take the mic to reclaim their identities out of the shadow of their infamous spouse. They remix five hundred years of historical heartbreak into an exuberant celebration of 21st century girl power. Previews: February 13, 2020. Tickets on sale through September 2020.

Celebrities on Broadway

Plaza Suite Comedy Play

See More: Celebrities on Broadway and List of NYC Broadway Shows

More: Discount Broadway Tickets

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Lincoln Center - Opera, Ballet, NY Philharmonic, Jazz, Broadway

You really haven't been to NYC until you experience THE beating heart of our Arts & Culture scene, Lincoln Center, home to the New York Philharmonic, Metropolitan Opera, NYC Ballet, Julliard School, Broadway and so much more. See what NYC's (always amazing) classic cultural scene has to offer while you are here.

Lincoln Center NYC

More: Lincoln Center Venue Guide

NYC Ballet Spring Season: April 23 – June 2, 2019

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Fleet Week New York City

Fleet Week New York City

2020 TBD
May 22-28, 2019

Thousands of Sailors, Marines and Coast Guardsmen from U.S. Navy and U.S. Coast Guard ships have come to NYC nearly every year since 1984. Fleet Week is the City’s celebration of the sea services and provides an opportunity to see the latest capabilities of today’s Navy, Marine Corps and Coast Guard Team.

Fleet Week includes dozens of military demonstrations and displays, as well as public visitation of many of the participating ships. Ship Tours are held at Pier 88 and in Staten Island, daily Thursday – Tuesday, from 8:00 a.m. to 5 p.m.

More on Fleet Week:

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Things To Do in New York in May

The best Things To Do in New York in May include boat & sailing tours, exploring NYC on bike, volleyball, tennis, cheering on the Mets and Yankees and basically anything else outdoors as May is a phenomenal weather month.

Things To Do in New York in May

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Fun Things to do in New York in Spring

Things to do in New York in Spring

There are hundreds of fun things to do in New York in Spring. With the cherry blossoms, green foliage, sparkling rivers and warm weather as your backdrop, Spring is the time to take advantage of rooftops, biking, tennis, volleyball, walking tours and so much more.

Here are some of our top picks for Fun Things to do in New York in Spring.

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Metropolitan Museum of Art (Met) Rooftop Open

Metropolitan Museum of Art (Met) Roof

April 16 - October 27, 2019
Iris and B. Gerald Cantor Roof Garden
The Roof Garden is open daily and The Martini Bar is open Friday and Saturday evenings (5:30-8 pm)

Skyline Views, Art and Cocktails - what more could you want?

Every summer, the Met opens the Martini Bar on the Roof Garden Café, an 8,000-square-foot, informal, outdoor setting with breathtaking panoramic views of the Manhattan skyline and Central Park.

More info: 2019 Met Roof Martini Bar Schedule.

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Five Boro Bike Tour (by TD Bank)

NYC Five Boro Bike Tour

Sunday May 3, 2020
(usually the first Sunday in May)

Watch or ride with over 32,000 cyclists spinning 42 miles through all five NYC boroughs, ending in Staten Island, where a fun outdoor Festival awaits. See bike demos, a mountain bike stunt show, food, product samples, massage and more.

More Info: www.bike.nyc

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Biking in New York City

Biking in New York City can be incredibly safe and fun, as long as you follow a few rules. If you don’t want to worry about helmets, locks, mapping routes and getting lost, then check our top picks for Bike Tours of NYC:

Things to Do in New York With Kids

  • New York Highlights Bike Tour (3 hrs) - good for all ages, offer bike trailers and baby seats, helmets, guides, from Harlem to the Brooklyn Bridge (9 miles).
  • Guided Bike Tour of Central Park - guided two-hour bike tour through our amazing 843 acres, seeing Strawberry Fields, Cherry Hill, Tavern on the Green, Bethesda Fountain, Onassis Reservoir, the Alice in Wonderland Statue, Cleopatra’s Needle and the Dakota
  • Brooklyn Bridge Bike Tour (2 hrs) - cycle around Manhattan’s southern tip, climb uphill into the City Hall area, then up onto the Brooklyn Bridge, a steady climb of about 15 minutes.
  • New York Pass - includes choice of bike rentals and tours: Blazing Saddles, Brooklyn Bridge Sightseeing Bike Tours and Rentals, Central Park Sightseeing Bike Tours & Rentals and more!
  • More Biking in New York City - details on DIY tours, best places to eat on the water and more.

See: Biking in New York City – more details on DIY tours, best places to eat on the water and more.

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Ninth Avenue International Food Festival

Ninth Avenue Food Festival NYC

2020 TBD
May 18-19, 2019; 10:00-6:00 pm
42nd-57th Sts, along 9th Avenue

Voted the Best Street Fair in NYC, taste the best of the best Manhattan food, on the cheap, on one street. Kids and adults will be entertained and fed until you’re stuffed! Admission free, food costs vary.

Come for Argentinian, Brazilian, Cajun, Chinese, Cuban, Dominican, Ethiopian, French, German, Greek, Haitian, Indian, Indonesian, Irish, Italian, Japanese, Mexican, Moroccan, Pakistani, Polish, Puerto Rican, Peruvian, Senegalese, Sicilian, Southern, Spanish, Thai, Trinidadian, Turkish, Ukrainian, Vietnamese food – and more!

Info: www.ninthavenuefoodfestival.com

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Affordable Times Square Hotels

Some of our top value picks in Times Square include:

Cheap Hotels in Times Square

See More: Cheap Hotels in Times Square

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Taste of Tribeca

Taste of Tribeca

2020 TBD
May 18, 2019

A great event for both adults and kids, this culinary festival brings together Tribeca’s best restaurants: Bouley, Bubby’s, Chanterelle, Tribeca Grill and more. Prior event cook offs included the Lamb Meatball Masters Challenge and Tang’s Natural Dumpling Challenge. General tickets allow for 6 tastes from some of New York’s finest chefs. $40 advance, $45 day of. Info: www.tasteoftribeca.com

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Boutique Downtown Hotels New York

Boutique Downtown Hotels put you right next to some of NYC's most popular attractions: The 9-11 Memorial and Museum, Statue of Liberty, One World Observatory, Wall Street, St. Paul's Cathedral, Charging Bull and every major subway station.

Boutique Downtown Hotels New York

Some of our top boutique accomodation picks downtown include:

See More: Boutique Downtown Hotels New York

More Downtown Hotels: Tribeca/Battery Park and Financial District/ Wall St

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Washington Square Outdoor Art Exhibit – FREE

Washington Square Outdoor Art Exhibit NYC

Memorial Day Weekend 2020
May 23-25 and May 30-31; 12pm – 6pm

Walk around Greenwich Village browsing tons of artwork displayed by original artists. Paintings, sculpture, eco-friendly art and lots of other unique pieces to see or purchase, at far less than gallery prices.

Location: It is a sidewalk show, not a street fair, and has its venue on University Place, starting at East 13th Street and continuing south along the east side of Washington Square Park to West 3rd Street.  The southern end of the show encompasses Schwartz Plaza, (aka Bobkin Lane), between NYU’s Shimkin Hall and Bobst Library.. More Info: www.wsoae.org

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Annual Intrepid Museum Summer Movie Series

Intrepid Museum Summer Movie Series

2020 TBD
May 24 – August 16, 2019 (select Friday Nights)

Enjoy FREE sea, air & space themed movies under the stars all summer long on the Flight Deck! 2019 Movies: Top Gun, Dunkirk, TBD, First Man, Community Choice Pick.

The flight decks opens at 7pm, film begins at sunset. Bring your lawn chairs, picnic baskets and blankets. Guests are encouraged to bring their own food, snacks and non-alcoholic beverages, however no outside alcohol is permitted.

More Info:

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NYC Airport Guides - LGA, JFK, EWR

Our detailed NYC Airport Guides go in-depth on everything you need to know about each airport. Free shuttles, nearby hotels, Stay & Fly Free Parking, Taxis, Limos, Shuttles, Parking, Cheap Flights and more.

More New York City Events May

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New York Yankees Schedule

New York Yankees Tickets

The New York Yankees, 27-Time World Series Champions, and likely the most simultaneously loved and hated team in baseball, return to Yankee Stadium with our newest star recruit, pitcher Gerrit Cole. There are few things in NYC better than a Yankee game, an old-fashioned hot dog and a beer.

NY Yankees Schedule – Home Games May



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New York Mets Schedule

New York Mets Tickets

Catch NYC's National baseball team in action at the amazing Citi Field, one of baseball's nicest stadiums. Tickets are easy to get and the Mets are an easy 30 minute subway from Times Square or Grand Central. Grab a burger from Shake Shack and get ready to see some baseball action.

NY Mets Schedule – Home Games



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Rangers MSG Schedule

New York Rangers Tickets

Get your New York Rangers tickets and schedule to see our NY hockey team live in action at Madison Square Garden. The NY Rangers have made the finals and/or playoffs the last six consecutive seasons. Their games are the easiest sporting events in NYC to attend, right in Midtown Manhattan, a block from the Empire State Building.

NY Rangers Schedule – Home Games May



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Knicks MSG Schedule

New York Knicks Tickets

No matter how they are performing, Knicks games are always a blast and there's nothing like an event at MSG. Come join our NY basketball team live in action at Madison Square Garden, "The World’s Most Famous Arena." Go NYC style with cheap seats, fast paced sports action, hot dogs and beer and cheer on the New York Knicks today! As a general rule, with plenty of exceptions, basketball games start at either 7:30pm or 12:00pm, November through April.

NY Knicks Schedule – Home Games May



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Brooklyn Nets Schedule

Brooklyn Nets Tickets

The Brooklyn Nets at Barclays Center is a true NYC experience. They offer classic Brooklyn foods like Nathan’s hot dogs and Juniors’ cheesecake, and have Jay-Z as a part owner! Jay-Z's 40/40 club in the luxury sections of Barclays center serves drinks until 2am. With 2,000 seats at Barclay's Center costing $25 or less, professional basketball is now available to everyone! See Brooklyn's newest team bring it New York style.

Brooklyn Nets Schedule – Home Games May



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Things to Do in NYC by Month

Our Event Calendars show you exactly which events occur by day, but our Things to Do monthly guides highlight seasonal tours, bike rides, best time for boat cruises, when to buy tickets, the biggest sales and all the optimal times to do activities by month.

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Help US Help Our site visitors by promoting YOUR NYC business. Have a great NYC restaurant, hotel, store or attraction? Want to offer a coupon to our guests? Want to share your favorite parts of New York City? We want to hear all about it. Learn More: Promote YOUR Business on NYC Insider Guide

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Promote Your Business on NYC Insider Guide

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