Holiday Season in NYC

New York | United States

Holiday Season in NYC

The holiday season in NYC is magical. The city has so much holiday spirit, it actually inspired the famous poem ‘Twas the Night Before Christmas’. The weather is colder, the largest parade in the country takes over the streets Thanksgiving Day, ice skating springs up at Rockefeller Center under a dazzling Christmas tree, European style holiday markets abound the parks, and under the hustle and bustle of the city the mood becomes more festive. It makes for an enjoyable long weekend.

Length: 4 days – can add more if this is a full trip to visit NYC

Transportation: Walking/ Metro – This is a walking heavy trip, though we recommend you get a metro card first thing on landing from the airport or coming in by train – you’ll be using it. NYC’s metro is the best way to get around. You can also use taxis/lyfts/ubers for more difficult locations/connections.

Movie Inspiration: Miracle on 34th Street, Elf

Best Guide Book:

Day 1 – Uptown

Day 2 – Midtown

Day 3 – Artistic New York

Day 4 – Brooklyn

In Depth Itinerary

Day 1 – Uptown

Central Park in late fall

If you’re coming from the airport you’re most likely flying into JFK, LaGuardia, or Newark. From LaGuardia, take a bus to the subway. JFK take the air train to LIRR. From Newark it’s most likely easiest to take a bus to the Port Authority or train. Depending on if its rush hour these may or may not be longer than grabbing a cab, but they’re certainly cheaper.

For lodging we recommend: The Library Hotel, The Lexington, Bryant Park Hotel, or Park Terrace Hotel. New York is expensive and that’s just something you have to accept. We recommend you try and stay somewhere in midtown for the easiest access to everything. Bryant Park is a nice area in which to stay, but we’ve also had luck around Penn Station. Of note, NYC is cracking down on AirBnbs so there is a potential risk associated with that choice. If you’re looking for something cheaper you can consider the Moxie, but we have to give it mixed reviews after our stay.

it’s also wise to dress warmly and comfortably today. Start today by heading to the Frick Collection Museum. Get off at 72nd metro stop and walk to museum. While not as famous as The Metropolitan Museum of Art or the Guggenheim, this museum is housed in a lovely brownstone mansion along Fifth Avenue, and houses famous art of Vermeer, Titian, El Greco, Van Dyck and Rembrandt. It’s especially lovely during the holiday season when the city is mobbed and it’s cold outside. It’s a perfect quieter way to start your day.

From the Frick Museum, head to Central Park. Lovely all time of year, it’s a delightful (albeit cold) walk in a winter wonderland. Head first to The Mall, aka a long promenade in the park of trees arching over the many street artists selling wares. Head to Wollman Rink, right in the park, and enjoy one of NYC’s iconic winter activities: ice skating. If you’re going to ice skate in the city, this is our recommendation. It can be slightly less crowded than other rinks and offers a beautiful view of the NYC skyline. Even if you don’t skate, spend a few minutes enjoying those that do whirl around the ice.

Next head to Tavern on the Green for lunch. Tavern on the Green embraces the holidays with a gusto. You’ll get a full dose of holiday cheer with their fantastic decorations while eating great fare. Make reservations ahead!

After you warm up with lunch, it’s time to visit your first holiday market: Columbus Circle Holiday Market. Part of what makes NYC so much fun in the holiday season is its European-style holiday markets. Enjoy wandering around the stalls selling their craftwork, food, and drink. They’re large and charming – some house 150 vendors.

With your wallet perhaps lighter, it’s time to wander along Fifth Avenue’s window displays. As you’ve probably noticed, the city goes all-out for the holidays and the store fronts of 5th Avenue are no exception. Department stores try and outdo each other in their cheer with lights, scenes, and decorations (often themed). Stroll down Fifth Avenue from 58th to 34th street to enjoy the storefront decor. The ornate displays can attract many people, so wait your turn for a view of the window. Stop and enjoy a coffee or hot chocolate along the way.

Our recommended walk starts at the Plaza Hotel (near Columbus Circle). Duck in to enjoy the decorations and if you’re in the mood, warm up with a coffee or cocktail in old NY elegance. Next, head down Fifth Avenue to Bergdorf Goodman between 58th and 57th streets. From there head to Tiffany and Co across the street and head inside for their decorations. Next walk to St. Patrick’s Cathedral between 51st and 50th streets. If open, head inside and appreciate the history, quiet, and peace. From the cathedral make your way to Saks Fifth Avenue between 49th and 50th. If you have more stamina you can head all the way down to 34th Street to Macy’s famous window display (probably the most famous of them all). The display is typically both on Fifth Avenue as well as Broadway. Inside Macy’s you’ll find Santaland at Macy’s, a fully decorated Christmas explosion (trees, elves, trains, snow) that ends with a visit to Santa. While you’ll see a lot of kids kids, adults are welcome too, and it will give a giant dose of holiday cheer. Reservations are required.

Once you finish your walk (or get too cold to continue) it’s time for dinner. We recommend an option from our NYC Restaurant Recs page.

Winter in Central park

Day 2 – Midtown

Ice Skating in Bryant Park

Today start with a visit to NYC’s most famous museum – the Metropolitan Museum of Art. It’s a not-to-miss site any time of the year, but it embraces holiday magic just like everything else. During the holiday season stop by the Medieval Sculpture Hall to enjoy the Met’s magnificent 20 foot blue spruce tree as well as the 18th century Neapolitan nativity scene at its base. The museum will take you a few hours so by the time you finish it will be close to lunch.

We recommend leaving the museum and walking down along 5th Avenue. There are somewhat limited options nearby if you don’t like hot dog trucks, over-touristed and overpriced fare, or want to walk 20 minutes east, however Cafe Sabarsky offering Austrian food in the Neu Museum and Russ & Daughters offering Jewish delicacies in the Jewish Museum are under the radar finds. You don’t need a ticket to either museum, you just have to enter it to get to the dining area.

If instead of lunch you would rather an elegant NYC experience of high tea, step back into old world Manhattan elegance at the Palm Court in The Plaza Hotel (starting at lunch time).

Next make your way to Rockefeller Center and Rockefeller Plaza to enjoy a National Landmark of old buildings, famous buildings, cool sculptures, and of course, NYC’s biggest Christmas tree and most iconic ice skating rink.

From Rockefeller Center walk to Bryant Park and the Bryant Park Winter Village. Our favorite Holiday bazaar in the entire city, this one offers 150 vendors, good food and drink, and is situated right next to the NYC Public Library. If there’s time and you’re cold, pop in to marvel at the beautiful building, map room, and consider the vast literary treasures that sit under Bryant Park (where you were so recently standing).

Grab a casual dinner at one of the stalls in Bryant Park, then head to a show in the evening. You can either opt for a Holiday themed show including: Radio City Rockettes’ Christmas Spectacular, The Nutcracker at the NYC Ballet, A Christmas Carol on Broadway, A Christmas Carol at the Merchant’s House, or a holiday concert at St. Patrick’s Cathedral, St. John the Divine, or the NY Philharmonic. Or if you’re wanting a break from holiday themed activity, head to a show on or off Broadway.

If you need a bite to eat or drink after your show, check out a spot in Hell’s Kitchen on our NYC Restaurant Recs page.

For lodging, stay in the same place as the previous night (night 2/3)

The Chrysler Building

Day 3 – Artistic New York

Dress warmly today and wear your walking shoes. Head over to 34th Street and 12th street (near the Hudson Yard subway stop) and climb the ramp up to the High Line. NYC’s urban park created on an old railway line, the High Line offers a park reprise in the middle of the city as well as sweeping views of the city. It’s beautiful all times of the year. Stroll along the roughly 1.5 mile path to the exit at Chelsea Market.

By this time you’ll probably be cold. Head into the market offering an impressive array of restaurants, coffee shops, and markets. Grab lunch at one of the options that grabs you. After you’re done browse the pop-up holiday shop the market hosts.

Next head to the Whitney Museum of American Art. While not as famous as the NYC Met, Guggenheim or MOMA (and yes, you can opt for one of those instead), this museum offers up an amazing collection from famous American artists including Georgia O’Keeffe and Jasper Johnson. It’s well worth the visit (and in the right neighborhood for the day).

After the museum make your way to the Union Square Holiday Market. Grab a hot beverage at the market and browse the over 150 vendor booths.

Next, enjoy Greenwich Village. Consider a Holiday walking tour to stay in the spirit. Or if today is a Friday, Saturday, or Sunday enjoy the 2pm Literary Pub Crawl where you’ll learn about the history of the village. If it is not Fri-Sun or you prefer, do your own self-guided tour, options tours include this one and this one or pick your type of self-led tour here.

For dinner you should absolutely not miss Rolf’s. A german eatery, Rolf’s explodes in Christmas decoration and holiday cheer (along with great food and beverage). Make a reservation to ensure a spot, it’s very popular.

After dinner enjoy a show at nearby jazz club Blue Note, who at the holidays invites artists including Chris Botti for a holiday concert. Or catch a show on Broadway where you can’t go wrong.

Day 4

Brooklyn Bridge

You have an option this morning.

Option 1) If you feel like an adventure in the morning, head up to the Bronx to the New York Botanical Gardens Holiday Train Show where you can either visit with kids or let your inner kid loose marveling at trains, ferries, and trollies whiz past 175 NYC landmarks.

Option 2) Head to Grand Central Station to enjoy the beauty of the building and experience another (inside this time) holiday market.

After this, we recommend you spend the rest of your day in Brooklyn. Brooklyn is a great area adjacent to Manhattan and with enough time in NYC, shouldn’t be missed. Start by walking across the Brooklyn Bridge which will offer incredible views of Lower Manhattan. It’s a fun walk and very easy.

Next head to the DUMBO (Down Under the Manhattan Bridge Overpass) neighborhood with cute shops and good restaurants. If you enjoy art, not only will you love the stunning street art adorning buildings, but you can pop over to the A.I.R. Gallery, the first all-female art cooperative gallery in the US. Consider lunch at The River Café, Cecconi’s, or Juliana’s. If it’s a beautiful day you may want to explore Brooklyn Bridge Park (spreading out directly below the Brooklyn Bridge on either side). And on that note, head to Jacques Torres Chocolate DUMBO to grab a hot chocolate for the next portion of your journey.

If it’s the weekend, head to the Brooklyn Flea Market. If a drink is more your thing than hot chocolate, you can stop along the way to the flea market for a holiday drink at Mace or Maison Premiere. The Brooklyn Flea Market offers This market offers a great holiday market open Saturdays and Sundays from 10 – 6.

As the lights go down, it’s time to hit up NYC’s best light show. Cab/uber/lyft to the Dyker Heights Neighborhood where you’ll see a light show unlike any other. Beginning in the 1980s as a friendly competition amongst neighbors, people now come from all over the city to enjoy it. The Dyker Heights tour has become legendary and is growing every year. Residents of the neighborhood create masterpieces of lights and holiday decorations in each yard as they try and outdo each other on decorating. You can walk yourself around the neighborhood or grab a tour on foot or bus. The best lights are on 10th Avenue to 13th Avenue and from 80th to 86th Street. We recommend grabbing an uber/lyft/taxi to get to the neighborhood from DUMBO (though you can opt to take the train back to Manhattan).

You can train or cab back to Manhattan from Dyker Heights. Once back, head to one of our NYC restaurant recs.

Bid NYC adieu either that evening or the next day.

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