The Ultimate Guide to NYC During the Holidays

*Updated 10.28.23

I have a really hard time deciding what my favorite time of year is in NYC – spring is gorgeous, the lush green of Central Park in the summer is beautiful and the change of the leaves in the fall is something to absolutely live for. But when it comes to the holidays in NYC, there truly is magic in the air! I’ve officially spent 10 holiday seasons in NYC and I couldn’t be more excited to share this post with you. I thought I’d break it up by area of the city and if you’re interested, here’s a link to a three day itinerary (including suggestions for where to stay and what to pack) I’d follow if I were visiting! I’ve also created a 17 page guide with a link to a custom Google Map you can purchase here – it has everything from the best décor, where to eat before/after a holiday show, activations and kid-friendly activities (including where to find Santa!).

Without further adieu, here is my guide to the most wonderful time of the year in the greatest city in the world!

MIDTOWN

Rockefeller Center – it’s hard to decide which is more iconic: the tree or the ice skating rink. I remember growing up and seeing the ice rink in the background of the Today Show and it was so fun to finally check this off my list in 2021. Make sure you buy your tickets in advanced and note you buy them for a set time and have 60 minutes to skate from the arrival time of your ticket (so if you’re late, your time on the ice gets reduced!). The tree is beautiful both during the day and the evening but if you can time it right, I think dusk is the best – you still get a little light around the buildings and the lights glow really beautifully. *Note the tree lighting is Wednesday 11.29.23.

Radio City/Christmas Spectacular – the Radio City Christmas Spectacular with the Rockettes is such a classic holiday performance and a super fun way to spend an evening (or a late afternoon), but in my opinion, as a single adult it’s one of those things you only need to do once (but would be fun to bring kids to).

Fifth Avenue Window Displays – take a stroll along Fifth Avenue between 48th Street and 59th Street and you’ll encounter some of the best store window displays you’ve ever seen. Between Saks Fifth Avenue, Tiffany & Co, Bergdorf Goodman and everything in between, it’s worth taking the stroll and giving yourself some time to take everything in. Also worth mentioning, the Saks Fifth Avenue display comes to life every hour with music and light show and it’s absolutely spectacular. *This year Christian Dior is doing a takeover of the light show and an activation of the ground floor in Saks – I can’t wait to check it out when they unveil it on November 20th.

Hotel Holiday Décor – while you’re strolling Fifth Avenue, pop into the Plaza, the St. Regis and the Peninsula to experience their holiday décor. One year I grabbed a glass of champagne at the Plaza in their cozy Rose Club with some friends before I went home for the holidays and it was magical! The Peninsula is a stop you absolutely cannot miss. Their lobby, while on the smaller side, is pure magic and their rooftop bar, Salon de Ning, converts the outdoor portion into a chalet themed bar so definitely grab a drink up there if you have time! And not far from Fifth Avenue (only a block away from Saks) is the Lotte New York Palace hotel. The outdoor tree in the courtyard facing Madison Avenue is quite literally my favorite tree in Manhattan. While the inside of the hotel is also beautifully decorated, the large outdoor tree makes for the perfect festive photo op. Due to construction, they didn’t set one up in 2021 or 2022 so tbd if there will be one again this year – the photo below is from 2018.

Sixth Avenue Holiday Décor – the buildings between 46th to 57th Streets really go all out with their holiday displays. The giant candy canes at 1271 Avenue of the Americas are newer in the décor roster and there’s also now a giant tree in the redesigned plaza at 1221 Avenue of the Americas. It’s definitely worth a stroll along the Avenue in the evening to soak it all in!

Bryant Park Winter Village – between the really well done holiday market and the ice rink, Bryant Park is a holiday hotspot! The holiday market has evolved in the most amazing way over the years and the vendors are really something special to check out. This year they have cozy igloos you can rent out and you can also stop by The Lodge for food and drinks overlooking the ice rink (and the rink is the city’s only free admission rink!). Check out this website for all of the info on the Bank of America Winter Village at Bryant Park.

New York Public Library Tree – if you’re checking out Bryant Park, it’s definitely worth your time to stop by the New York Public Library. Each year the tree in Astor Hall is dressed to the nines (and the inside of the library is just as spectacular in its own right!). *Note the library has been undergoing renovations so TBD if they will put up a tree display this year.

Grand Central Holiday Fair – in the event it’s absolutely freezing, this is an indoor option for those looking to check out a holiday market.

FLATIRON/THE VILLAGE

Union Square Holiday Market – typically the Union Square Holiday Market is buzzing with activity, similar to the Bryant Park Market. But due to COVID, it will not be opening this year.

Washington Square Park – this is always an iconic NYC stop but the tree under the arch is really special to see at night. I actually only saw it for the first time in 2018. I was doing some holiday shopping on Fifth Avenue and while walking to dinner at Minetta Tavern I went through the park and spotted it. Such a nice surprise! If it’s a clear night and you angle your camera right, you can capture the Empire State Building in the background of a photo.

West Village – if you have time, wandering through the neighborhood is totally worth it because you’re likely to discover many of the townhouses and buildings are festively decorated. I made a guide and custom Google Map of all my favorite photo spots to save you some time while exploring!

Dine at Rolf’s – known for it’s 15,000 ornaments and over 100,000 holiday lights, an evening dining at Rolf’s is what holiday dreams are made of. Even if you’re not a fan of German food, I highly suggest making a reservation (and making it early) and finding at least a snack or drink on the menu just to experience the festiveness.

Serra by Birreria – this is Eataly Flatiron’s seasonal rooftop restaurant and they really go all out each season. Every winter they mix up the décor but I can promise you, if you’re looking for good food in a winter wonderland, this is the restaurant for you.

230 Fifth – if drinking inside an igloo on an NYC rooftop sounds like your idea of a party, head to 230 Fifth Avenue.

DOWNTOWN

Brookfield Place – between expansive dining options, family-themed events, the ice rink and the Luminaries light display, a trip to Brookfield Place should be on your list. Luminaries is a really unique light display that’s been around for a few years now and I’m so glad they keep bringing it back! And while most of the shopping is pretty high end, it connects through to the Westfield World Trade Center mall so there’s shopping options for every budget.

Pier 17 at the South Street Seaport – this downtown destination has become quite the hot spot and has really revamped the area since Hurricane Sandy. Every winter they create an ice rink on the roof and this year’s theme is Disney’s The Santa Clauses’ Winter Wonderland (aka they’re bringing The North Pole to Manhattan!). I highly recommend a reservation – check out their site to sign up for the waitlist to be notified when reservations are available!

Wall Street Tree (in front of the NYSE) – Wall Street is a quick walk from Pier 17 and World Trade Center, so it’s easy to stroll by and check it out. My favorite vantage point down there is to climb up a few steps at Federal Hall (26 Wall Street) so you can get a picture above the crowds (*note Federal Hall has been undergoing renovations so TBD if the steps will be uncovered by the holiday season).

UPTOWN

Central Park – if it snows during your trip to NYC, you must make it to Central Park. You should take a walk through the park anyway, but a stroll through to park in the snow is the best. If you’re coming from Midtown, I highly recommend entering near the corner of 59th/5th and walking north on the path until you get to the Mall and Bethesda Terrace. These spots are a little touristy, but so iconic. And you can pause at Gapstow Bridge along the way to look over the pond at the Plaza Hotel and other buildings on 5th Avenue.

The Nutcracker – I know I suggested the Radio City Christmas Spectacular and said it’s good to go at least once but I could literally go to the Nutcracker every year and it would never get old. Between the gorgeous David H. Koch theater and the costumes and just the fact that it’s a classic, the Nutcracker is a must do on your holiday trip to NYC.

UES townhouses – my neighborhood, the Upper East Side, is well known for it’s simple, but chic holiday décor. Think of it as all the townhouses wrapped up like presents! There are a bunch of townhomes in the 60’s between Park and Fifth Avenues, some in the 70’s anywhere between 5th and Third Avenues (that’s a lot of ground to cover, but there’s a ton nestled in that area!), and a handful in the 80’s – some between 5th and Park Avenues and others between Lexington and Third Avenues. If you don’t want to hunt *too* hard, I created a guide and custom Google Map to all the best photo spots in the UES. And while you’re there, make sure to plan a stop at Ralph’s Coffee for festive décor and a warm drink (Ralph’s can get crowded and can feel a little overrated, but the festive décor is 1000% worth it).

Serendipity 3 – a classic establishment where you can grab a frozen hot chocolate!

WORTH THE TRIP

Dyker Heights Christmas Lights – if you’re staying in Manhattan, this will be a bit of a trek, but I’ve heard it’s 1000% worth it. The Dyker Heights neighborhood of Brooklyn goes ALL OUT every single year. They operate a tour bus from Manhattan near Bryant Park to do a guided tour and also offer guided walking tours. Or if you want to do your own thing, you can either hire a driver or grab a cab (might get pricey though!) to take you on a ride through the neighborhood. Have your hotel help you with the transportation if you want to go it on your own.

New York Botanical Garden – with both the Holiday Train Show and NYBG GLOW, there’s a lot to do at the Botanical Garden during the holidays. Also a bit of a trek from Manhattan but totally worth it, the Botanical Garden’s holiday activities cater to everyone. For the train show, they recreate New York Landmarks out of natural materials and set up model trains to zip through the scenery and GLOW is a beautiful outdoor light display. *Due to COVID this year, reservations are restricted to members only. Be sure to check the website for all the details and book early!