Your guide to New York City’s can’t-miss holiday happenings

Nov 24, 2019

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When it comes to Christmas in the city, New Yorkers mean business. From open-air holiday markets to rooftop ice rinks and spectacular light shows, there’s something new to see and do around every corner. With so many options, we decided to highlight some of our favorites to help with your planning.

Better yet, we created a TPG map that you can download to Google Maps and use on the go.

Related: Follow @thepointsguy on Instagram to see Liz and Haley conquer the NYC holiday happenings

Prepare to get in the holiday spirit because we’ve got quite the list for you. Here’s the TPG guide to holiday happenings in New York City:

In This Post

Holiday-themed shows

Lots of things come to mind when you think of New York City — bright lights, tall buildings, the constant sound of honking and the more pleasant thought: seeing a show. After all, New York is the home of Broadway. There are dozens of shows, but in the spirit of the season, here are some of our favorite holiday shows:

Radio City Music Hall Christmas Spectacular featuring The Rockettes 

Take a break from the cold, sit back and enjoy a lively show from the Radio City Rockettes. The Christmas Spectacular runs until Jan. 5, 2020, giving you plenty of time to see this holiday show. However, we’d highly recommend seeing the Christmas Spectacular, well, before Christmas.

You can currently snag tickets for as low as $49. If you have a card like the Chase Sapphire Preferred® Card or even a Chase debit card, you can access exclusive reserved seats at some of the best showtimes when you use your card. Be sure to select “Chase Cardmember Preferred Seating” when checking the “Type” on Ticketmaster.

The Nutcracker

This classic ballet makes its annual reappearance at the Lincoln Center starting on Nov. 29, 2019, and running until Jan. 5, 2020. The show’s not quite as lively as the Rockettes, but it is beautifully mesmerizing. Tickets to the ballet start at $60 and go up to $300 for orchestra seats.

Catch a classic on the big screen

If you’re looking to escape the cold, but don’t necessarily want to pay the higher ticket price of a live show, then consider seeing a classic holiday movie at the theater. For example, you can watch Elf at United Palace on Dec. 15 for just $15. 

Holiday markets

When it comes to holiday markets in the city, there are quite a few. We are highlighting some of the most well-known ones in Manhattan given their proximity to other fun holiday happenings in the city. 

The Grand Central Holiday Fair is a great market to stop at if you’re catching a train in or out of the city. By comparison to the other markets, it’s rather small but there are beautiful handcrafted items by local and regional artists. If you need to refuel, The Great Northern Food Hall is across from the Holiday Fair booths and offers Nordic-inspired food, notably hot soup and excellent bread. Or, you can can grab a bite to eat at Grand Central by heading downstairs to the Grand Central Market where the options range from Shake Shack to Magnolia Bakery. Grand Central Holiday Fair runs through Dec. 24, 2019.

Pro-tip: If you’re looking for a little magic, head to the Grand Central Terminal Whispering Gallery across from the Grand Central Oyster Bar on the lower level. Once you’re there, have a friend head to the corner opposite from you. Tell them to put their ear up to the wall and then whisper sweet nothings to them. They’ll be able to hear it clearly even over the hustle and bustle of Grand Central Terminal.

If you’re looking to kill two birds with one stone — ice skating and a market — head to Bank of America’s Winter Village at Bryant Park. This European inspired open-air market features artisans from around the world and many based right here in NYC. The shops are housed in custom-designed glass huts, so you can briefly warm up while checking out potential gifts. 

To me, the Union Square Holiday Market feels like the epitome of what a Christmas Market should be. If you enter through 14th and Union Square East side, you’ll pass under a garland festooned arch and will immediately be met with the smell of cedar wood, pine and cider donuts. You can then browse through the 150 local vendors that fill market. There are plenty of yummy food options like warm pierogi, giant pretzels or chocolate-covered waffles. If you just want to sit down and take it all in, head to the Citi Holiday Lounge with warming stations and lounge seating. You can also sip on hot cocoa or charge up your phone, all compliments of Citi and Urbanspace.

If you’re exploring the Upper West Side of Manhattan, then you may want to consider a stop at the Columbus Circle Holiday Market. If you want to add this to your plans, it’s worth noting that it doesn’t open until Dec. 4 and only stays open until Dec. 24, 2019.

Union Square and Winter Village will remain open until early 2020. 

Lights and sites

They don’t call it the “City That Never Sleeps” for nothing and that rings even truer around the holidays. Although Times Square is lit up year-round, the rest of New York follows suit as early as Halloween and really ramps up around Thanksgiving. Here are some of our favorite lights and sites around the city.

Take a walk down Fifth Avenue 

When you take a stroll down Fifth Ave, you’ll get to see some of the most beautifully decorated window displays in the city. It’s always fun to see how creative the stores can get with their products and themes. 

One of the most iconic and must-see displays is the Saks Fifth Avenue Holiday Light Show. This year’s theme is Frozen 2 and the opening night, Nov. 25, 2019, will feature a live performance from Tony winner Idina Menzel and a 50-person choir. 

The light show will run on a nightly basis from 4:30 p.m. to 11:30 p.m. throughout the holiday season. For prime viewing, head across the street to get the full view of the 10-story display. Fifth Avenue gets extremely busy around this time of year, so if you want front-row viewing, you’ll have to arrive early and stand your ground.

Get into the spirit at 30 Rockefeller Plaza

I think it’s safe to say that 30 Rock is basically the epicenter of Christmas here in NYC. You can do it all — from seeing the world-famous Rockefeller Center Christmas Tree, to skating around The Rink, browsing the toy selection at FAO Schwarz or heading over to Radio City Music Hall to see The Rockettes. There are even some fun surprises like a pop-up igloo bar from City Winery where you can warm up after hitting the ice.

If you want to see the Rockefeller Tree all lit up, you’ll have to wait until Dec. 4, 2019, when a live performance will precede the tree lighting at 8 p.m. After the first lighting, visitors can see the iconic tree until Jan. 17, 2020. And if you can’t make it to the city this year, you can watch the televised tree-lighting ceremony and performances on NBC.

Visit Santa at Macy’s

If you’re a family visiting the city, you’ll probably want to stop by and visit Santa at Macy’s Santaland. However, be sure to make reservations in advance as they are required. 

Reservations are free and will open on Nov. 25, 2019. Note that the slot you are given is not the time you will get to see Santa, but the time that you can get in line. The wait time depends on the day of the week and how close it is to Christmas. Macy’s elves suggest visiting Monday through Wednesday earlier in the season to minimize your wait. Santa will begin seeing visitors on Nov. 29, 2019, the day after he arrives in the Big Apple on his sleigh at the end of Macy’s Thanksgiving Day Parade. 

“Shine On” at Hudson Yards

If you’re looking for something a little less traditional, but still festive, head to Hudson Yards where you’ll find a glowing installment called “Shine On.” The installment will launch on Nov. 29, 2019, and according to the site, is “a dramatic indoor-outdoor artistic light and music installation coupled with seasonal events and experiences for the whole family.” Every day at 5 p.m., you can catch a glimpse of Christopher Schardt’s Lyra. It’s a series of star-shaped sculptures that create a visual phenomenon, and it’s all set to a holiday-season soundtrack. The sculptures are each comprised of 12,000 controllable LED lights. Translation: You’re about to see this all over Instagram.

There will be more “Shine On” events, including Wells Fargo’s Lodge, complete with a 360-degree photo booth, hot chocolate sampling, holiday selfie cookies, charging stations and more. Find a full list of events here.

Ice skating

Yes, we did make an entire category dedicated to ice skating spots in the city because, frankly, there are a lot. We’re here to tell you that there’s much more than The Rink at 30 Rock. Here’s our list and break down of the prices:

Pier 17 Winterland Rink

One word: rooftop. Yep, this rink is on the rooftop at Pier 17 and overlooks the East River with prime views of the beautiful Brooklyn Bridge. After a visit to the rink, I must say this is an awesome twist on a classic winter activity. However, it’s not quite as cozy as the rinks that have the protection of surrounding buildings and trees so make sure you bundle up to fully enjoy the views. 

Weekdays: Rink admission $15; rink admission and skate rental $23
Weekends: Rink admission $18; rink admission and skate rental $26
Peak days: Rink admission $27; rink admission and skate rental $35

Children under 5 years old skate free, but skate rental is not included. There’s also a neighborhood discount up to 30% for those who live in the Seaport District.

If you’re feeling fancy, you can elevate your night with a Winterland special Veuve Clicquot VIP Package, which starts at $41 on average days and $50 during peak days. The package includes admission, skates and one glass of Veuve champagne after skating.

The Rink at Rockefeller Center

Alright, this is definitely a classic and is a must-do on a lot of people’s lists. There’s no denying that skating under the 77-foot decked out tree in the middle of Manhattan is pretty spectacular, so here’s what you need to know before you go: 

Standard pricing: Adult admission $25; children and senior admission $17, and skate rental $18
Holiday pricing: Adult admission $28; children and senior admission $17, and skate rental $18
Peak holiday pricing: Adult admission $35; children and senior admission $17, and skate rental $18

The Rink at Bryant Park

What’s great about ice skating at Bryant Park is that it’s almost free. And completely free if you bring your own skates. That’s right, there’s no admission fee if you want to skate around the 17,000-square-foot rink. This is a steal compared to the other rinks in the city. Here’s the breakdown of the skate rental prices:

Standard: $18

Weekends/peak: $23

Peak holiday: $33

The Rink at Brookfield Place

To escape the madness that is Midtown, head to Battery Park where you can skate around a waterfront rink with views of the Hudson at Brookfield Place. To get into the holiday spirit, there will be performances of a “Holiday Ice Concert” on Dec. 10 and 11, 2019, at 7 p.m., created and produced by U.S. Olympic skaters, Melissa Gregory and Denis Petukhov.

When it comes to price, this is another affordable option. However, skaters are given a 90-minute time limit. Here’s what you can expect to pay at Brookfield:

90-minute admission: $15

Skate rental: $5

Wollman Rink at Central Park

Another classic spot to hit the ice is at Wollman Rink in Central Park. What makes this rink special is that it’s in the park itself on top of The Pond — a very traditional ice skating experience. Better yet, the lights from buildings surrounding the park make for a beautiful backdrop. If you happen to catch it on a snowy day, you may even be able to get in some sledding. 

Unfortunately, you won’t be able to earn any points or miles on this experience. This is a cash-only venue: 

Weekdays: Adults $12; children (11 and under) $6; seniors $5, and  skate rentals $9
Weekends/holidays: Adults $19; children (11 and under) $6; seniors $9, and skate rentals $9

Best spots for festive drinks

It’s the time of year when your Instagram feed is flooded with shots of festive frou-frou drinks. NYC is home to thousands of bars which are constantly coming up with Instagrammable concoctions and decor, so we’re just going to let the pictures do the talking on this one.

Best restaurants with festive decor

New York City is a foodie mecca. You want it? We got it. Given the sheer number of options, it can be hard to narrow down where to eat — that’s why the TPG foodie, Samantha Rosen, put together a list of some of the best restaurants in New York City. However, if you’re a total geek for the holidays, all the way from the lights to the bites, then you may want to check out some of these festive restaurants.


Rolf’s is a German restaurant known for completely decking out its space for the holidays. It’s as if you’re looking at your Christmas tree from the inside out. The menu features classic German dishes like schnitzel and, of course, there’s German beer on tap. Rolf’s is a fan favorite of holiday lovers, so it fills up early. If you want to get a seat, reservations can be made via phone.

Panna II

If you feel like you haven’t seen enough lights yet and are a fan of Indian food, head down to the East Village to Panna II. The restaurant features Christmas lights year-round with hundreds of bulbs draped from wall to wall. Beware if you’re on the taller side, as this restaurant definitely wouldn’t pass the TPG shower test. But if you don’t mind ducking to get to your seat, you’ll enjoy some delicious relatively inexpensive food. Panna II also allows you to BYOB, so be sure to stop by a bodega and grab some beer or the liquor store for some wine. You’ll also want to bring a fair amount of cash. Credit cards are not accepted here. 

Rock Center Cafe

If you’re staying in Midtown and plan to do all the 30 Rock holiday activities, you might as well add the Rock Center Cafe to your list. The cafe looks out onto The Rink, so you can watch skaters glide by (or fall) as you enjoy food with the family. You can also make reservations to have breakfast with Santa now through Dec. 24, 2019, but it you might run up quite the tab with tickets up to $125 per adult. 

The Plaza Palm Court

With famous Christmas movies like Home Alone II and Eloise being filmed here, it’s no wonder why everyone wants to make a stop at The Plaza over the holidays. Speaking of movies, you can reserve tea at The Plaza Eloise style, but it’ll run you a couple hundred. If you still want to experience The Plaza at Christmas then brunch at the Palm Court could be a good alternative. Another more affordable option is heading down to the food court where you’ll have a much wider selection of food to chose from.

Holiday-themed hotel rooms 

If you want to eat, breathe and sleep in the holiday spirit then you may want to check out this over-the-top Elf themed suite at the Wyndham Midtown 45.

This exclusive holiday suite will become bookable on Nov. 25 at 10 a.m. EST and will start at $399 a night. The bookings comes with four complimentary passes to the Empire State Building and Rockefeller Center to help you cross off some of Buddy’s NYC bucket list items.

Getting to NYC

If you haven’t already planned your trip to New York, you’re most likely going to see pretty high prices at the holidays. However, there’s still hope you can snag a good last-minute deal. Be sure to put a Google Flights tracker alert on potential travel dates. Google will notify you of any price changes and you can act on any deals.

Beyond that, if you’re set on experiencing the city during the holidays, use points and miles. Although it likely won’t be the best redemption of your points, it could save you hundreds in cash that you can put toward ice skating at The Rink or gifts at the holiday markets.

If you live within a reasonable distance, consider taking a train or bus. You can typically grab cheap last-minute bus tickets on Megabus, Greyhound and OurBus. My favorite place to look for cheap tickets is on Wanderu. As for the train, Amtrak is good about running sales frequently. If you live close enough for a day trip then you can take advantage of Amtrak’s 2-for-1 deals on select routes available on Saturdays. Another deal worth mentioning is Amtrak Share Fares, which offers discounts up to 45% on groups of six. Taking the train or bus not only saves you some serious cash, but it’s also super convenient because the drop-off locations are within the city and you won’t have to worry about paying for parking in the city.

Bottom line

Christmas in New York is unlike any other. There’s no better way to get into the holiday mood than walking around the city with a cup of hot cocoa while admiring all of the decorations. 

Before you head out to explore, be sure to map out your day. It’s possible to cross off quite a few items in just one short day, but planning is key. Check out our map to get an idea of how you can see the most.

Want more advice for planning a trip to New York City? Visit our new destination hub, and check back throughout the week for hotel guides, restaurant recommendations and more.

Featured photo courtesy of imagenavi/Getty Images.

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