Holiday To-Dos in New York City

Hi there, friends! How are you? I hope you’ve gotten a great start to the New Year.

I feel like we have some catching up to do, and the first place I want to start is highlighting a lot of what we’ve been up to over the holiday season in New York City. Scott and I had several groups of visitors between Christmas and New Year’s and we practically walked the entire city. More than once. It was exhausting, but also exhilarating and inspired me to share my list of must-sees around NYC during the holiday season!

I hope you enjoy reading today and be sure to return next week when we’re back to chatting the usual favorites. Happy Friday!

Things To Do in New York City During the Holidays

• Holiday Nostalgia Train

It’s so fun to ride the holiday train! It’s a vintage subway train straight from the 1930s that is only used during the holiday season between Thanksgiving and New Year’s. All you need is a quick search of the train schedule and a metrocard to catch a ride. The train runs on the F line and starts at 2nd Avenue in Lower Manhattan. It goes all the way up to 145th street and can get crowded. You’ll most likely see people dressed in vintage clothing and a lot of photoshoots during the stopping points!

• The Radio City Rockettes Holiday Spectacular

I’ve seen this show over a handful of times and it’s just as cool now as it was the first time. (Special shout out to my good friend Lauren who was in the show for ten years!) The show doesn’t change much from year to year, and that’s part of the charm. Over one million attend per season, and a lot of those people make it an annual tradition with their families. The girls are dazzling and extremely talented, and the show also features skits with Santa, an ode to The Nutcracker, and a live nativity scene.

• Central Park Ice Skating

While a lot of people chose to fight the crowds for the chance to go ice skating at The Rink at the Rockefeller Center, you’re better off going to Wollman Rink at Central Park. We went a few days after the New Year and the lines weren’t crazy at all. Plus, the views of the city skyline are killer.

• 5th Avenue Windows & Saks Fifth Avenue Light Show

I’d recommend starting all the way by the park (after ice skating!) and stopping into The Plaza Hotel for a warm treat before you go! It’s neat to see the location where Home Alone was filmed, and they have an underground market with food, drinks, shops, and public restrooms — which is something you’ll want to keep in mind while touring around Manhattan.

Once you’re done, head down Fifth Avenue and check out all of the holiday showcases while you window shop. All of the stores up their display game around the holidays, the most notable being Bergdorf Goodman. The displays are unreal. You’ll definitely want to make a stop by Saks Fifth Avenue (the best view is directly across from the Rockefeller Tree) and stick around until you see the popular light show that runs every ten minutes. It’s magical!

• Rockefeller Tree

If you’re in town early enough, you could catch the Rockefeller Tree Lighting during the first week of December. Be prepared for a heavy crowd, however, as spots are first come first serve. The tree stays lit until the end of January and is truly a spectacle to see in person. We went through a lot of the routine you just read a few times this holiday season, as we had different visitors in town throughout the last week of December and first week of January. If possible, try to go see the tree any other time besides the days leading up to New Year’s Day. That was the busiest I’ve seen yet and was almost impossible to navigate with a stroller. Even the third of January was much, much better.

• Top of the Rock Observation Deck

This was a new one for us this year, and it was also very crowded, as we went on New Year’s Day. You can purchase tickets to the Top of the Rock any time of the year, but I wanted to add it to this list because of the extra lights you’ll get so see from a top deck of the city! (Check out the bottom left of the photo above — it’s the Macy’s holiday windows mentioned later in this post.)

• Bryant Park Winter Market & Union Square Holiday Market

I love Bryant Park. It’s provides a refresh to touristing around with an open-air market, just streets from from Times Square. The winter time is extra special because there is more than a hundred boutique shops, food, and an ice skating rink! Skyler loves riding the carousel, and we always take visitors by the park on our tour through the city! The holiday market is open by November and runs through the first week of January.

Union Square Holiday Market is another big one worth the trip! Located in Union Square Park, this one has a warming station, live music, and just under a hundred tents with gifts from local craftsman, artists, and vendors. There’s so much to do and see!

• Rolf’s

While we didn’t make a trip over to Rolf’s this year, it’s a must-see for sure. The German restaurant and bar is located in Gramercy Park and is well known for its over-the-top holiday decorations. The best part about it is that the cheer stays up year round.

• Macy’s – Herald Square

If you’re looking for more windows to explore, don’t miss Macy’s at Herald Square. There are six window displays, all incredible and linked to a theme each year. This year there were several components that incorporated live interaction that included taking your picture and petting a giant dog!

• Dyker Heights Christmas Lights

If you’re looking to see more suburban light strolling, then head down to the southwest corner of Brooklyn and over to Dyker Heights. The area draws locals and tourists alike, with elaborate Christmas decorations, life-size Santas, music, and more. You can purchase tickets for a tour by foot and bus, or just get there and explore on your own. Word to the wise, however, you’ll want to take the train or a car service, as parking isn’t always available.

• Brooklyn Bridge Fireworks

If you’re here around the New Year, you’ll be able to see fireworks from most roof tops! One of the best spots to view them is by the Brooklyn Bridge. I’ve never made it out there, but I have seen them from the rooftop of our building. There is also an impressive display in Prospect Park (in our Park Slope neighborhood)! Enter at Grand Army Plaza for refreshments and even live entertainment before the new year turns.

• Times Square Ball Drop

This one definitely isn’t for everyone, as the crowds are a lot. If you aren’t looking to stay on a budget, then I’d recommend researching restaurants near the area that host a New Year’s Eve “ticket” to dinner, drinks, and an escort experience to see the Ball Drop. I’ve been lucky enough to do this twice, thanks to Scott’s former employment at Hunt & Fish Club. It certainly isn’t cheap, but it is a one-of-a-kind experience that allows you to see the ball drop and only be in the crowds for about twenty minutes. Phew!

If you are looking to brave the crowds, check out these helpful tips for survival. It’s suggested to arrive early in the afternoon to get a spot, and you’ll want to come full, layered up, with an empty bladder, and with a lot of patience, as you will most likely have to stand your ground to keep your spot. Either way, seeing the actual ball drop that airs on television every year is an incredible experience! There’s more confetti than you can even imagine, and starting a new year off in those steps feels liberating.

May the odds be ever in your favor!

While New York is a fun place to visit and even cooler place to live, I highly recommend everyone coming to see the city around the holidays. There’s so much more that I could have added to this list and never enough time to do it all. If you have any more suggestions, please add them in the comments below.

Until next year!