New York Holiday Moments Not To Miss

December 8, 2022

The Best Holiday Moments in NYC I wit & whimsy

This time of year my inbox and DMs always become full of questions regarding the best things to do in New York City during the holidays. Since it had been several years since I last did a post on things not to miss during this festive season, I wanted to put together an updated comprehensive guide with all my favorites. 

What to Do in New York During the Holidays

What to see in New York City at Christmas

Fifth Avenue Windows

Start at Bergdorf Goodman and then head down Fifth Avenue to Tiffany & Co., Saks Fifth Avenue and more. Don’t forget to look up at the decorations on some of the buildings like Harry Winston, Cartier; among others while you’re at it!

Upper East Side Home Tour

The Upper East Side townhomes go all out for holidays and Christmas is no exception. The most memorable ones are in the 70s between Fifth Avenue and Madison.

Sequin Romper I wit & whimsy

Saks Fifth Avenue Light Show

I absolutely love the Saks light show that happens outside the store every ten minutes once it is dark out. The music, display and lights is a little slice of magic across the street from the Rockefeller Center Christmas tree.

Palace Hotel Christmas Tree I wit & whimsy

The Palace Christmas Tree

Take a detour from the Christmas windows along Fifth Avenue and pop over to The Palace Hotel’s courtyard to see their gorgeously adorned tree (where these photos were snapped.) The entrance to the courtyard is off of Madison Avenue.

Holiday Dress

The New York City Ballet ‘s The Nutcracker

A personal favorite holiday tradition of mine is to get dressed up and see The Nutcracker at Lincoln Center! It is so special to get all dressed up, have a fun dinner beforehand and see this beautiful ballet. The first time I saw it I was awe-struck. Do not miss buying tickets to this beautiful performance. It delights every, single year.

New York City Christmas Ice Skating

Ice Skating in Central Park

There are several places to skate in New York this time of year, but I love the Wollman rink in particular since you get to take in the park and the towering buildings above. A few things to note to make your visit better: 1. it is cash only; 2. no bags are allowed on the ice so plan accordingly and 3. it is pricey so you may want to plan to stay awhile! Bring a snack to have while you rest your feet.

Other places to consider skating? Rockefeller Center and Bryant Park! Bryant Park has the penguins to help little ones try their hand at skating, too.

Holidays in New York City

Rockefeller Center Christmas Tree

This destination practically goes without saying! I always love getting a glimpse of the magnificent site of this tree every season. All lit up and something to truly marvel at. Put some Christmas music in your ears, drown out the crowds and look up in awe. It’s wonderful during the day but perhaps even better at night!?

Christmas in New York

More adventurous? Join the skaters on the Rock Center skating rink!

The Best Holiday Moments in NYC I wit & whimsy

The Radio City Christmas Spectacular

Cheesy but a true delight and of course an iconic New York City Christmas tradition. I’d recommend doing it once to say you have! It’s also fun to hear the little ones’ commentary throughout!

Plaid Pants Holiday Outfit I wit & whimsy

Hot Chocolate

Warm up with hot chocolate all across the city. You’ll find rich, thick hot chocolate in the French style at Angelina and Laduree or you’ll find a variety of vendors selling it at the Christmas markets that pop up all across the city.

Union Square Christmas Market

New York City boasts several Christmas markets but the Union Square one is my personal favorite. I love shopping at the local businesses showcasing their goods and having some mulled wine while doing so.

New York Philharmonic

They always have some amazing holiday programming I like to attend and this weekend I can’t wait to see their Holiday Brass concert on Sunday!

Rolf’s German Bar

This spot is famous thanks to Instagram and while it is wildly crowded nowadays, you have to make a stop here for a spiked eggnog or mulled wine. Go late at night or arrive before opening to get in line on a weekend and enjoy your drink under the best Christmas decorations any joint has ever offered. This place is like drinking inside of a Christmas tree!

Bryant Park NYC Holidays I wit & whimsy

Winter Village at Bryant Park

I love how Bryant Park transforms this time of year with the additions of a skating rink (seen here) and their Winter Village of shops curated with treats and fare from small businesses.

Dyker Heights Christmas Lights

Dyker Heights

A sure-fire way to get in the holiday spirit, this Brooklyn neighborhood goes all-out when it comes to home decor. The lights, music and displays are amazing. I recommend bringing some hot cocoa in tow in a reusable cup. Come bundled as you’ll be walking through the neighborhood for some time to see all the lights.

Christmas in New York City

New York Hotel Lobbies

I love popping into iconic New York Hotels to see how the decorate this time of year and many often have installations out front, too! I recommend seeing The Carlyle, The Plaza, The St. Regis and The Peninsula. Get your girlfriends or family together, some hot drinks in hand and do a hotel lobby crawl! Note that you can’t go into The Plaza during regular operating hours and they only open it to guests after 8PM unless you have a reservation for the restaurant or bar.

The Standard East Village Winter Garden

The Standard opened up this winter garden a few years back and it’s a cozy favorite spot of mine this time of year! During the day they are selling Christmas trees but at night you can reserve a yurt and have a fondue party or just grab a table to sip on mulled wine or hot cider cocktails. All the lights and the blankets make this spot so cozy.

Bemelmans Bar NYC

Bemelmans Bar

This place is like traveling back in time to old New York. Between the dark wood-covered walls, famed murals by Ludwig Bemelman and piano music drifting in the air, you can’t help but feel elated when you settle in and the Manhattan hits your hand. Take in the lights on Madison Avenue and the decorations in at The Carlyle as you make your way to the bar.

Expect a line so arrive early! They open mid-day so if you don’t mind drinking in the afternoon you can usually get a seat then otherwise lines usually begin around 4PM – especially during the holiday season! It is snug so not a lot of seats available but also since the drinks are so pricey tables do tend to turn over quickly.

The St. Regis King Cole Bar

My favorite special occasion bar in Midtown. Be sure to capture your photo with the giant nutcrackers standing guard outside this storied hotel this time of year.

Holiday Train Show at the Bronx Botanical Garden

This is such a fun activity to do with kids during the holiday season! See more than 25 G-scale model trains and trolleys hum along nearly a half-mile of track underneath recreations of NYC’s most famous bridges.

The Best Holiday Moments in NYC I wit & whimsy

And of course, when you’re seeing the Christmas sites, it is only fitting to have the perfect festive ensemble. If you need some ideas head to my Party Attire Picks.

Have you been to New York City during the holiday season? I’d love to hear what you enjoy doing!

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comments +

  1. Melanie says:

    This look is FIRE! Absolutely stunning!

  2. GF says:

    you absolutely have the best “holidays in NYC” content! I have friends visiting me in NYC this holiday season; excited to try some of these ideas with them!

  3. Annie says:

    That nutcracker look – my GOLLY, you look beautiful!! Also love the entire category of “New York Hotel Lobbies” … these are all wonderful NYC holiday ideas!

    Big hugs xxo! – Annie from

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