NYC 2019 May Activities, Things to Do and Events Calendar

New York City Events May 2019 include Billy Joel, Cher, P!nk 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. Our newest Broadway Shows include Beetlejuice, Tootsie, Be More Chill, Hillary and Clinton and more.

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 2019, 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 24th for the whole weekend. Please check sightseeing hours for Memorial Day, Monday, May 27, 2019 and be sure to treat Mom on Sunday, May 12th.

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

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Taking the Stress out of NYC Group Transportation

Taking the Stress out of NYC Group Transportation

Tired of flagging down taxis? Don’t feel like deciphering public transportation routes? Sick of your straggler group members ending up lost? We feel your pain. Traveling through New York City with a large group can be a hassle. The dazzling lights, bustling streets, and occasional celebrity sightings create the perfect storm for a frenzy of excited group members dashing around from one street corner to the next, when all you wanted to do was enjoy a simple trip to the Met with your group. More Info: Taking the Stress out of NYC Group Transportation

New York City Timeshares

New York City Timeshares

For an upscale New York City getaway that won't break the bank, consider New York City Timeshares. Timeshare rentals in Manhattan, New York are located conveniently in Midtown Manhattan, the heart of the city, making it easy to experience famed local attractions. Whether you are a savvy NYC traveler or someone looking to hit all the tourist hot spots, NYC timeshare apartments are the perfect homebase for your getaway. More Info: New York City Timeshares

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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 2019

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

Sunday, May 12, 2019

Top Picks Include:

Choose from special Brunches and Dinners, Broadway shows, free cocktails and open bars, tons of special Manhattan Cruises, chocolate tours, the Mets, 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 Our FREE NYC Printable Guide (Mini Version)

Browse Below and Download Here: FREE NYC Printable Guide (Mini Version)

I wanted to let you know how much I enjoy the insider guide and maps. It is exactly what I was looking for and trying to search the internet for weeks and still did not find even a fraction of what you have in your guide. Even something as simple what direction avenues and streets run was not something I thought of or found any information on but is very important. Exactly what I was looking for. Don’t waste your time researching and trying to find all this information online when you can get it in the insiders guide. Wonderfully put together and extremely helpful. Thank you. - Mary Margaret (October 2018)

NYC Printable Map Guide Book

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.

L-O-V-E this guide! It's well thought out, easy to read and easy to follow with a very sensible layout. I can tell whomever wrote this put a heck of a lot of thought into every section. Thanks so much for this awesome book. This is going to make this our best NYC trip by far. --Brenda, PA

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)

NYC Printable Guides - Available for Immediate Download

NYC Printable Map Guide Book
NYC Printable Map Guide Book

NYC Map Guide Printable Bonus
BONUS NYC Maps

New York City Travel Guide
NYC Travel Guide

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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.

Most Popular New York City Tours and Activities

Statue of Liberty and Ellis Island: 4-Hour Guided Tour (StatueTour)

Likely to sell out
Price starting at US$51
View details

Compare New York Pass Options and Save

Price starting at US$20
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Empire State Building: Silver Access (86 + 102 for Fee)

Likely to sell out
Price starting at US$34
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THE RIDE Bus Tour

NYC Insider Pick
Price starting at US$60
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All Access: 911 Memorial Tour, Museum & Observatory

Bestseller
Price starting at US$100
View details

One World Observatory: Skip The Line (Priority Reserved)

Likely to sell out
Price starting at US$34
View details

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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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Best May New York City Vacation Packages

Memorial Day & Fleet Week NYC Vacation Package

With the great weather, and many New Yorkers escaping on the weekends, May is a great time to book your NYC Vacation Package. Choose from all inclusive:

All New York City Vacation Packages include Hotel, Taxes, Free Attractions and Museums, Discounts, Maps, Vacation Planning Assistance and more.

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Memorial Day Weekend NYC

Memorial Day NYC

May 24-27, 2019

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 2019

Shakespeare in the Park NYC

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 2019

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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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Superfine! Art Fair NYC

Superfine! Art Fair NYC

May 1-5, 2019
107 Grand Street, SoHo

Superfine! Art Fair NYC, where punk rock spirit meets art market innovation. More than just any other art fair, Superfine! is a place of discovery. Expect hand-curated, accessibly-priced works by top new contemporary artists in a friendly, welcoming atmosphere, along with thousands of New York’s art aficionados eager to snatch up a new piece. Works begin at $100, 90% of pieces are priced under $4,000.

Read More: Superfine! Art Fair NYC

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Will a New York City Discount Pass Save You Money?

New York City Attractions Pass Compared. Which is the BEST – New York City Explorer Pass, New York Pass or New York City Pass? Get savings coupons and find the best New York City Pass Discounts for your NYC vacation.

Save with a New York City Pass

Get savings coupons and find the best New York City Pass Discounts 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

NY Explorer Pass
New York City Explorer Pass

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Broadway Shows May 2019 Top Picks

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

Beetlejuice Broadway Musical Tickets

Beetlejuice Broadway Musical

Beetlejuice tells the story of Lydia Deetz, a strange teenager obsessed with the whole “being dead thing.” Lucky for Lydia, her new house is haunted by a recently deceased couple and a degenerate demon who happens to have a thing for stripes. When Lydia calls on Beetlejuice to scare away anyone with a pulse, he comes up with the perfect plan involving exorcism, arranged marriage and a girl scout who gets scared out of her wits. Previews March 28, Opens April 25, 2019. Ages 12+

Tootsie Broadway Musical

Tootsie Comedy Musical

Based on the classic film, Tootsie tells the story of a talented, but difficult-to-work-with actor who will do anything to land the role of a lifetime - including adopting a new, female persona, Dorothy Michaels. His audacious, desperate stunt lands him the role of a lifetime,only to cause complete comedy and chaos in his life. Previews March 29th, Opens April 23, 2019.

Be More Chill Broadway Musical

Be More Chill Broadway Musical

Joining the great white way after rave Off-Broadway reviews, Be More Chill asks you, What if teenage popularity came in a pill? Would you take it, no questions asked? Achieving the “perfect life” is now possible thanks to some mysterious new technology—but it comes at a cost that’s not as easy to swallow. What could possibly go wrong?. Previews Feb 13th, Opens March 10, 2019. Ages 12+

Hillary and Clinton Broadway Comedy

Hillary and Clinton - Laurie Metcalf, John Lithgow

Behind closed doors in New Hampshire during early 2008, a former First Lady named Hillary is in a desperate bid to save her troubled campaign for President of the United States. Her husband, Bill, sees things one way; her campaign manager, Mark, sees things another. Hillary and Clinton examines the politics of marriage, gender roles, and the limitations of experience in this profound and timely look at an American dynasty in crisis. Previews Feb 13th, Opens March 10, 2019.

Full List of Broadway Shows and Discount Broadway Tickets

Celebrities on Broadway

Network Broadway Play Bryan Cranston

See All: Celebrities on Broadway

Full List of Broadway Shows

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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

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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Sunrise from the Artist’s Balcony Art Exhibit

Sunrise from the Artist's Balcony NYC Art Exhibit

April 16-May 11, 2019 – Exhibition
April 27, 2019 – Artist’s Reception

Come check out one of NYC Insider Guide’s FAVORITE artists at her newest exhibit, Sunrise from the Artist’s Balcony. Ellen paints the most stunning images of NYC – the Highline, Rooftop Skylines and more. Now, she’s given us an up close and personal view from her 25th floor window, with spectacular views.

More Info: Sunrise from the Artist’s Balcony NYC Art Exhibit

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Five Boro Bike Tour (by TD Bank)

NYC Five Boro Bike Tour

Sunday May 5, 2019
(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

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

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 2019
May 25-27 and June 1-2; 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: near NYU, University Place from E 10th Street, South along Washington Square Park to W 3rd Street. The South end of the show, Schwartz Plaza, is also known as Bobkin Lane. More Info: www.wsoae.org

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Martin Lawrence Gallery Showcases Nautical Magic of Kerry Hallam

Martin Lawrence Gallery Showcases Nautical Magic of Kerry Hallam

May 1-31, 2019

For the entire month of May, Kerry Hallam’s unique acrylic paintings on authentic nautical charts, highlighting ports of call from New York City to the Islands of Hawaii, will be available for acquisition at MLG’s Soho gallery, beautifully framed and delivered with a hardback copy of Kerry’s autobiographical book Getting To Nantucket. Hallam’s works spirit us away to experience an alluring atmosphere and the simple pleasures of life.

More Info: Martin Lawrence Gallery Showcases Nautical Magic of Kerry Hallam

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Annual Intrepid Museum Summer Movie Series

Intrepid Museum Summer Movie Series

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 the new Yankee Stadium. There are few things in NYC better than a Yankee game, an old-fashioned hot dog and our new Yankee Stadium.

NY Yankees Schedule – Home Games May



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New York Mets Schedule

New York Mets Schedule

Catch NYC’s National baseball team, and last year’s World Series contenders, in action at the awesome 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. Check out the NYC Insider Guide to New York Mets Tickets, Schedule and Directions.

NY Mets Schedule – Home Games


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New York Rangers 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. With our All-Star goaltender Henrik Lundqvist, the NY Rangers bring us some serious hockey action. Entering their 91st season, the Rangers have built their reputation on pride, passion, tradition and truly die-hard fans. 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

The NY Knicks, in their 71st Season, have a great roster, so come join our NY basketball team live in action at Madison Square Garden, “The World’s Most Famous Arena.” As a general rule (with plenty of exceptions), evening basketball games start at 7:30 and daytime at 12:00pm.

More Info: NY Knicks

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 and check our insider guide to Brooklyn Nets Tickets, Schedule and Directions!

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.

Promote YOUR NYC Event on NYC Insider Guide

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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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