New York City for the Holidays

Is there anything more magical than New York City for the holidays?

We planned the trip on a bit of a whim, and as we neared closer to December and the temperatures kept dropping, I was worried we’d made a horrible mistake. Walking around New York City during the busy holiday season, pushing a stroller in the freezing cold…what were we thinking?

Clearly we booked this trip when it was 90 degrees and sunny.

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Where to experience the holiday season in New York City! // Family Travel | Travel with Kids | Christmas in NYC | Rockefeller Plaza | 5th Avenue | Macy's Santa | Christmas Markets | US Travel | United States | America | White Christmas | Holiday Travel | Winter Travel

But, we actually lucked out big time. The weather in the city was absolutely gorgeous during our visit and perfect for seeing the city. Temperatures hung in the mid-50’s, and even hit the mid-60’s on a couple of days. We shed our winter coats and were able to walk almost everywhere we went.

Where to experience the holiday season in New York City! // Family Travel | Travel with Kids | Christmas in NYC | Rockefeller Plaza | 5th Avenue | Macy's Santa | Christmas Markets | US Travel | United States | America | White Christmas | Holiday Travel | Winter Travel

Where to experience the holiday season in New York City! // Family Travel | Travel with Kids | Christmas in NYC | Rockefeller Plaza | 5th Avenue | Macy's Santa | Christmas Markets | US Travel | United States | America | White Christmas | Holiday Travel | Winter TravelWe covered a lot of ground in 5 days. So much so, that trying to fit everything into one post would be outrageous. So instead, I’ll be sharing bits and pieces over the next couple of weeks, from the places we visited to the food we enjoyed.

But first things first (this was New York City in December after all), let’s get to the number one mission for the trip: catching some of that holiday spirit!

We got into town late Wednesday morning and took the long, slow cab ride from La Guardia into Manhattan. You could literally see the gears turning in Evelyn’s head as she tried to process all that was happening around her. There were so many people, cars, and buildings…everywhere! Almost an hour later, we pulled up to our new home for the week: a 27th floor Airbnb in Gramercy.

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Where to experience the holiday season in New York City! // Family Travel | Travel with Kids | Christmas in NYC | Rockefeller Plaza | 5th Avenue | Macy's Santa | Christmas Markets | US Travel | United States | America | White Christmas | Holiday Travel | Winter Travel

For me, easily the most stressful part of traveling with a baby is getting all of our gear to and from the airport. Luckily, when we arrived a doorman was there to help us lug our suitcases, stroller, and travel crib into the building. It was such a relief when we were finally able to drop everything inside the apartment. We laid out some blankets for Evelyn to play on the floor, did some quick unpacking, and then went out to the balcony to check out the view.

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Where to experience the holiday season in New York City! // Family Travel | Travel with Kids | Christmas in NYC | Rockefeller Plaza | 5th Avenue | Macy's Santa | Christmas Markets | US Travel | United States | America | White Christmas | Holiday Travel | Winter Travel

With the balcony facing west and no other tall buildings nearby, we had some amazing unobstructed views south as far as One World Trade Center and north all the way up to the Upper East Side. The apartment was in the perfect location for our 5 day trip for many reasons:  it was close to a ton of great restaurants in the Flatiron district, a short walk to several subway lines, easy access for getting in and out of Manhattan, and perfectly situated halfway between everything we wanted to see both uptown and downtown.

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Rockefeller Center

The next morning was our first full day in New York, so we figured we’d better start off with the most quintessential holiday activity in the city – a visit to Rockefeller Center! While we weren’t ready to lace up our ice skates just yet, we did get a chance to sit and watch those skating by under the big tree while Evelyn enjoyed a morning bottle. Thanks to the beautiful weather, we were able to sit on a park bench and take it all in, not having to worry too much about bundling up to stay warm. It was hard to believe it was the second week in December!

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Where to experience the holiday season in New York City! // Family Travel | Travel with Kids | Christmas in NYC | Rockefeller Plaza | 5th Avenue | Macy's Santa | Christmas Markets | US Travel | United States | America | White Christmas | Holiday Travel | Winter Travel

We tried to get some pictures under the Christmas tree, but Evelyn wasn’t cracking any smiles.

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Where to experience the holiday season in New York City! // Family Travel | Travel with Kids | Christmas in NYC | Rockefeller Plaza | 5th Avenue | Macy's Santa | Christmas Markets | US Travel | United States | America | White Christmas | Holiday Travel | Winter Travel

We strolled past the Today Show window where Matt & Savannah were delivering the morning news and then made our way inside Rockefeller Center. Of course, we couldn’t visit New York without a trip to the Top of the Rock! After taking in the views from the 70th floor, we made it back to street level, continuing along 5th Avenue where the high end storefront displays awaited us. Saks Fifth Avenue, directly across from Rockefeller Plaza, was fully decked out.

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Where to experience the holiday season in New York City! // Family Travel | Travel with Kids | Christmas in NYC | Rockefeller Plaza | 5th Avenue | Macy's Santa | Christmas Markets | US Travel | United States | America | White Christmas | Holiday Travel | Winter Travel

5th Avenue Decorated Storefronts

Also along 5th Avenue, Salvatore Ferragamo, Lord & Taylor, Tiffany’s and Harry Winston had some of my favorite decor. And you can’t miss the impressive window displays at Bergdorf Goodman. Just don’t visit on a weekend…the sidewalks are absolutely packed and you won’t be able to hardly move, let alone get a close up look at the displays. Instead, try to get out on a weekday morning when the streets are much quieter.

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Where to experience the holiday season in New York City! // Family Travel | Travel with Kids | Christmas in NYC | Rockefeller Plaza | 5th Avenue | Macy's Santa | Christmas Markets | US Travel | United States | America | White Christmas | Holiday Travel | Winter Travel

Where to experience the holiday season in New York City! // Family Travel | Travel with Kids | Christmas in NYC | Rockefeller Plaza | 5th Avenue | Macy's Santa | Christmas Markets | US Travel | United States | America | White Christmas | Holiday Travel | Winter Travel

Where to experience the holiday season in New York City! // Family Travel | Travel with Kids | Christmas in NYC | Rockefeller Plaza | 5th Avenue | Macy's Santa | Christmas Markets | US Travel | United States | America | White Christmas | Holiday Travel | Winter Travel

Where to experience the holiday season in New York City! // Family Travel | Travel with Kids | Christmas in NYC | Rockefeller Plaza | 5th Avenue | Macy's Santa | Christmas Markets | US Travel | United States | America | White Christmas | Holiday Travel | Winter Travel

Santaland at Macy’s Herald Square

No trip to NYC at Christmastime would be complete without a visit to Santa at the Macy’s flagship store at Herald Square. We arrived early the next morning to beat the long lines. Weekdays, first thing in the morning and early in the Christmas season are the best times to visit to avoid an exceptionally long wait.

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Where to experience the holiday season in New York City! // Family Travel | Travel with Kids | Christmas in NYC | Rockefeller Plaza | 5th Avenue | Macy's Santa | Christmas Markets | US Travel | United States | America | White Christmas | Holiday Travel | Winter Travel

We entered the huge department store through the Broadway entrance and took a few laps around the first floor before deciding we’d better ask someone for directions to Santa. Turns out, he’s actually kind of tricky to find. Save yourself the trouble and take the elevators right up to the 8th floor and head to the back of the store near the Au Bon Pain.

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Even if you get there early, expect to wait almost an hour or more before seeing Santa Claus; he’s in pretty high demand. Luckily the smart people at Macy’s have devised a clever way to keep your little ones interested while you wait. As we followed the winding road through “Santaland”, the anticipation kept building as signs continually reminded us how many steps were left to go. Slowly, we inched closer and closer, stopping for the occasional photo op. Finally at end of the road, an elf introduced herself and led us to Santa’s “hut”.

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Where to experience the holiday season in New York City! // Family Travel | Travel with Kids | Christmas in NYC | Rockefeller Plaza | 5th Avenue | Macy's Santa | Christmas Markets | US Travel | United States | America | White Christmas | Holiday Travel | Winter Travel

What the kids in line with us didn’t know was that there were actually 4 or 5 different Santa’s waiting to greet children, all hidden in their own “huts”. This is how they’re able to keep the line moving much quicker than your average mall Santa.

Don’t worry, with all of the excitement and anticipation, the kids didn’t even notice (and to be honest, as adults knowing the scheme ahead of time, we hardly did either).

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Where to experience the holiday season in New York City! // Family Travel | Travel with Kids | Christmas in NYC | Rockefeller Plaza | 5th Avenue | Macy's Santa | Christmas Markets | US Travel | United States | America | White Christmas | Holiday Travel | Winter Travel

By the time we made it to Santa, Evelyn was having a hard time staying awake and was so ready for her morning nap. We barely got a couple of sleepy pictures in before she gave up and fell fast asleep back in her stroller.

Where to experience the holiday season in New York City! // Family Travel | Travel with Kids | Christmas in NYC | Rockefeller Plaza | 5th Avenue | Macy's Santa | Christmas Markets | US Travel | United States | America | White Christmas | Holiday Travel | Winter Travel

Union Square Holiday Market

Later that afternoon after winding down from lunch at Gramercy Tavern, we decided to make a stop at the Union Square Holiday Market, a Christmas market similar to the more well-known Bryant Park Winter Village. We opted for Union Square simply because it was closer to our Airbnb and we weren’t up for another long walk.

The market was an eclectic collection of goods (mostly handmade), with everything from jewelry to puzzles, hats, and tasty treats. It was very busy though, and once again we had a hard time getting around some of the tighter walkways with our big stroller. We were sensing a pattern, and began to understand why New Yorkers invest in those fancier, slimmer strollers.

Where to experience the holiday season in New York City! // Family Travel | Travel with Kids | Christmas in NYC | Rockefeller Plaza | 5th Avenue | Macy's Santa | Christmas Markets | US Travel | United States | America | White Christmas | Holiday Travel | Winter Travel

The next day we continued our trend of walking everywhere, checking out Central Park and landmark buildings like Grand Central Station and the Chrysler Building in Midtown! But that afternoon, we got a little more than we’d bargained for.

After seeing all the sights, we found ourselves about 20 blocks from our Airbnb. We contemplated whether we should bother finding the subway entrance, but figured it would be an easy walk back down Third Avenue – about 30 minutes our GPS told us. So we opted to set out on foot instead.

Where to experience the holiday season in New York City! // Family Travel | Travel with Kids | Christmas in NYC | Rockefeller Plaza | 5th Avenue | Macy's Santa | Christmas Markets | US Travel | United States | America | White Christmas | Holiday Travel | Winter Travel

What we didn’t realize was that today was SantaCon NYC. Apparently this thing is a big deal, not only in New York, but in several major cities around the US (originating in San Francisco back in 1994). Thousands of people flock to the city dressed as Santa (along with the occasional elf) to essentially walk the streets and drink. With the high concentration of bars and young people from Murray Hill down to the East Village, we had plenty of company and got quite a show on our way home.

Where to experience the holiday season in New York City! // Family Travel | Travel with Kids | Christmas in NYC | Rockefeller Plaza | 5th Avenue | Macy's Santa | Christmas Markets | US Travel | United States | America | White Christmas | Holiday Travel | Winter Travel

I can almost imagine what people were thinking as we passed by, “Look at those out-of-towners, pushing their baby straight through a crowd of drunken Santas.” Whoopsie. Luckily the partying only lasted the night, and the next morning the streets were (exceptionally) quiet once again.

Where to experience the holiday season in New York City! // Family Travel | Travel with Kids | Christmas in NYC | Rockefeller Plaza | 5th Avenue | Macy's Santa | Christmas Markets | US Travel | United States | America | White Christmas | Holiday Travel | Winter Travel

Where to experience the holiday season in New York City! // Family Travel | Travel with Kids | Christmas in NYC | Rockefeller Plaza | 5th Avenue | Macy's Santa | Christmas Markets | US Travel | United States | America | White Christmas | Holiday Travel | Winter Travel

Festive Neighborhoods

Even though it didn’t quite feel like Christmas in the city, it certainly looked it. We loved strolling through the many different neighborhoods, seeing the classic greenery that decked the historic townhomes, schools and churches we passed.

I particularly adored the quaintness of the Village. “If we ever moved to the city, this is where we’d have to live,” Matt said. Something tells me that’s not happening anytime soon.

Where to experience the holiday season in New York City! // Family Travel | Travel with Kids | Christmas in NYC | Rockefeller Plaza | 5th Avenue | Macy's Santa | Christmas Markets | US Travel | United States | America | White Christmas | Holiday Travel | Winter Travel

Where to experience the holiday season in New York City! // Family Travel | Travel with Kids | Christmas in NYC | Rockefeller Plaza | 5th Avenue | Macy's Santa | Christmas Markets | US Travel | United States | America | White Christmas | Holiday Travel | Winter Travel

Where to experience the holiday season in New York City! // Family Travel | Travel with Kids | Christmas in NYC | Rockefeller Plaza | 5th Avenue | Macy's Santa | Christmas Markets | US Travel | United States | America | White Christmas | Holiday Travel | Winter Travel

And of course, even New Yorkers need Christmas trees! This floral shop around the corner from our Airbnb had quite the selection, both big and small.

Where to experience the holiday season in New York City! // Family Travel | Travel with Kids | Christmas in NYC | Rockefeller Plaza | 5th Avenue | Macy's Santa | Christmas Markets | US Travel | United States | America | White Christmas | Holiday Travel | Winter Travel

Where to experience the holiday season in New York City! // Family Travel | Travel with Kids | Christmas in NYC | Rockefeller Plaza | 5th Avenue | Macy's Santa | Christmas Markets | US Travel | United States | America | White Christmas | Holiday Travel | Winter Travel

If you have the chance to visit New York City, definitely consider a trip during the holiday season. There really is some special magic in the air, and even those tough New Yorkers are a little cheerier this time of year.

And how could you not be, with such beautiful surroundings?

Read Next: Foodie Parent’s Guide: Dining in New York City with a Baby

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Where to experience the holiday season in New York City! // Family Travel | Travel with Kids | Christmas in NYC | Rockefeller Plaza | 5th Avenue | Macy's Santa | Christmas Markets | US Travel | United States | America | White Christmas | Holiday Travel | Winter Travel
Where to experience the holiday season in New York City! // Family Travel | Travel with Kids | Christmas in NYC | Rockefeller Plaza | 5th Avenue | Macy's Santa | Christmas Markets | US Travel | United States | America | White Christmas | Holiday Travel | Winter Travel

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