A Very Merry Christmas Guide to New York City | www.agreatbighunkofworld.com | A Great Big Hunk of World
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A Very Merry Christmas Guide to New York City

Queue "Silver Bells" by Bing Crosby.

* This post has been updated for the 2019/2020 holiday season. Additional updates coming soon.

Queue “Silver Bells” by Bing Crosby.

If there is one thing I love most about New York City, it’s the way the atmosphere seems to change around the holiday season. There is something about the holiday lights shining bright amongst the city lights, while grey slush puddles shoppers fill the streets that just makes this city seem a little more magical.

I have always been a winter person. Some people tell me it’s because I was born in February, but I’ve always believed it’s because the holiday season here is like no holiday season anywhere else. After 25 years, I have yet to grow tired of all there is to experience at Christmastime, and I think it’s time to share the wealth.

The Holiday Shops

The Union Square Holiday Market – Union Square Park, Southern Side, New York, NY
November 21 – December 24, 2019
Nearest Subways: N,Q,R,4,5,6,L

While this area of Union Square is typically reserved for the Union Square Greenmarket, during the holiday season it transforms into a holiday market of approximately 200 vendors, selling everything from custom artwork, to handmade to jewelry, to leather goods.

A Very Merry Christmas Guide to New York City | www.agreatbighunkofworld.com | A Great Big Hunk of World

Winter Village at Bryant Park, 476 5th Avenue, New York, NY
October 31, 2019 – January 2, 2020
Nearest Subways: F,B,Q,R,N,6,1,2,3

Bryant Park’s Winter Village is by far my favorite of the Christmas markets and is the one I visit most frequently. With a huge ice rink and a 64-foot tree in the center of it all, it makes for a fun, half-day of holiday fun. Be sure not to fill up before dropping by; you don’t want to miss out on the macaroons, fried pickles, and Max Brenner Hot Chocolate.

A Very Merry Christmas Guide to New York City | www.agreatbighunkofworld.com | A Great Big Hunk of World

Grand Central Holiday Fair, 89 E 42nd Street, New York, NY
November 18 – December 24, 2019
Nearest Subways: 4,5,6,7,S

If you’re visiting New York for the first time, I’d be surprised if Grand Central Station wasn’t on your list of sights to see. Visiting around the holiday season technically makes this spot a two-for-one. This market is one of the only ones that lets you get in on the Christmas market fun without having to endure the New York winter outside.

A Very Merry Christmas Guide to New York City | www.agreatbighunkofworld.com | A Great Big Hunk of World | Photo: Marc A. Hermann / MTA New York City Transit

Columbus Circle Holiday Market, Central Park West and 59th Street, New York, NY
December 4 – December 24, 2019
Nearest Subways: Q,N,W,R,1

You’re in New York City, you’re within walking distance of Central Park (the 3rd most visited attraction in the world), and it’s Christmastime. Now add on the 50 vendors all selling unique crafts, art, food, and home accessories, and you’ve got a great day of holiday festivities. And while you’re in the area drop by the Columbus Circle Shopping Center where you might catch “Holiday Under the Stars” – A dozen 14-foot color-changing lights that dance to holiday music.

A Very Merry Christmas Guide to New York City | www.agreatbighunkofworld.com | A Great Big Hunk of World


The Holiday Shows

The Radio City Christmas Spectacular
November 8, 2019 – January 5, 2020

I’d be lying if I said I didn’t once dream of becoming a Rockette, but unfortunately, I stopped growing at about 5’4. Still, that never stopped me from my almost-annual tradition of going to see the Rockettes, live in action. Between the sets and costume changes, special effects, heartfelt storyline, and amazing dance numbers, this is a hard show to top when you’re visiting for the first time, and especially when visiting during the holiday season.

You can purchase tickets to the 84th year of the Christmas Spectacular here. Since tickets have been on sale since around July-August, I’d recommend snagging yours as soon as possible.

A Very Merry Christmas Guide to New York City | www.agreatbighunkofworld.com | A Great Big Hunk of World

The Nutcracker at the New York City Ballet
November 29 – January 5, 2020

For a little over a month each year, visitors can experience George Balanchine’s Nutcracker with the New York Ballet Company at Lincoln Center, a building worth a visit in it’s own right. Other season favorites also include Romeo & Juliet, and Swan Lake.

A Very Merry Christmas Guide to New York City | www.agreatbighunkofworld.com | A Great Big Hunk of World

A Christmas Carol at the Lyceum Theater
November 7, 2019 – January 5, 2020

A cast of only seven bring this classic alive, with a wonderful retelling of the story of Scrooge and his adventure with three Christmas spirits. Smaller in size, the Beckett Theater provides a more intimate feel than other large-scale theaters, which is exactly the type of environment needed for this show.

Handel’s Messiah, David Geffen Hall, 10 Lincoln Center Plaza, New York, NY
December 17 – December 21, 2019

Experiencing a performance by the New York Philharmonic should be on every New York bucket list. For one week, you can experience Handel’s “Messiah”, which is considered a holiday favorite. Tickets can be purchased here.

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Christmas Windows

Fifth avenue takes on a whole new vibe during the holidays, and I’ve never been able to go a season without a self-guided tour passed the Christmas windows. Designs range from mannequins dolled up in their finest holiday fashion, to avant-garde, light filled displays; to windows like those at Macy’s, designed and arranged to tell a new story each holiday season.

Macy’s Herald Square, 151 W 34th St, New York, NY
Nearest Subways: B,D,F,M,N,Q,R,W

A Very Merry Christmas Guide to New York City | www.agreatbighunkofworld.com | A Great Big Hunk of World

Lord & Taylor, 424 5th Ave, New York, NY
Nearest Subways: B,N,Q,W,R,2,4,5,6,7

A Very Merry Christmas Guide to New York City | www.agreatbighunkofworld.com | A Great Big Hunk of World

Saks, 611 5th Ave, New York, NY
Nearest Subways: B,D,F,M,1,6,N,Q,R

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Bergdorf Goodman, 754 5th Ave, New York, NY
Nearest Subways: Q,N,W,R,F,1,4,5,6

A Very Merry Christmas Guide to New York City | www.agreatbighunkofworld.com | A Great Big Hunk of World

Barney’s, 660 Madison Ave, New York, NY
Nearest Subways: Q,N,W,R,F,1,4,5,6

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Bloomingdales, 000 Third Avenue, 59th Street and Lexington Avenue, New York, NY
Nearest Subways: Q,N,W,R,F,1,4,5,6

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Tiffany & Co., 727 5th Ave, New York, NY
Nearest Subways: Q,N,W,R,F,1,4,5,6

A Very Merry Christmas Guide to New York City | www.agreatbighunkofworld.com | A Great Big Hunk of World


Ice Skating Rinks

One of my favorite lines, from one of my favorite films, P.S. I Love You is “If we’re all alone we’re all together in that too.” While Kathy Bate’s character wasn’t talking in the same context, I’ve always related it to New York City. Despite the fact that you can pass thousands of people on the street regularly, most New Yorkers tend to be caught up in their own little world. I always get chills when I’m skating around a packed ice rink with some friends, surrounded by dozens of smiling people altogether, while the city and Christmas lights glisten in the background. This may sound super cheesy, but I guess we can blame the Christmas spirit coming out a bit early this year.

Most ice rinks also stay open a months after the Christmas shop season has ended, so it’s a great addition to any itinerary for those who weren’t able to visit earlier in the season.

The Rink at the Bryant Park Winter Village, 476 5th Ave, New York, NY
October 31, 2019 – January 2, 2020
Nearest Transportation: F,B,Q,R,N,6,1,2,3

This one was mentioned earlier, but I’ll reiterate how much I recommend going. It’s the prime location, surrounded by holiday shops and might be the best time for you to whip out that pair of ice skates you have thrown in the back of your closet since skating is free but rentals cost a small fee. FYI, the line for the ice rink can often wrap around the entire perimeter of the park. Get their earlier in the day, and try to plan your visit for a couple of weeks before Christmas Day for the shortest wait time.

A Very Merry Christmas Guide to New York City | www.agreatbighunkofworld.com | A Great Big Hunk of World

Wollman Rink at Central Park, 830 5th Ave, New York, NY
October 20, 2019 – TBD
Nearest Subways: A,B,C,D,1,N,Q,R,F

The Home Alone vibes are alive and well here, at least for me since I’ve never been able to think “Central Park at Christmas” without thinking about my favorite Christmas movie. Wollman Rink is not as huge as some others, but the city skyline in the background and close proximity to Central Park definitely makes it a worthwhile spot. Price of admission runs about $12 per person, $6 for children under 11, and skate rentals run at $9, tax included.

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The Rink at Rockefeller Center
October 12, 2019 – January 4, 2020
Nearest Subways:B,D,F,M,1,6,N,Q,R

Skating at this rink is popular amongst visitors during the holiday season, due to it’s close proximity to Radio City Music Hall and the ever-so-popular Rockefeller Christmas tree. Since the price of admission is a bit higher than others, roughly $25-32 a person depending on the season ($15 for those under 11), and skate rentals at $12 per pair, this is a slight splurge when visiting with a large family. For those looking for a more in-depth experience, add-on’s like Breakfast with Santa and Christmas Spectacular tickets are available.

A Very Merry Christmas Guide to New York City | www.agreatbighunkofworld.com | A Great Big Hunk of World


Christmas Themed Bars

Some local bars go all out for the holidays, and while this list could be quite extensive, I’m going to share my favorite festive bars which all happen to be in pretty close proximity of each other. Holiday pub crawl, anyone?

Rolf’s, 281 3rd Ave, New York, NY

I have a love/hate relationship with Rolf’s. This German restaurant and bar have gone viral every year due to their insane amount of Christmas decorations, which stay up until sometime in May. The wait time, in my personal opinion, isn’t always worth it as pictures are quite deceiving in how large the space actually is. That being said, the holiday drinks are strong, and the decorations are in fact as outlandish but amazing as you’d imagine. If you don’t mind waiting in a 40-minute line to get in, definitely make this stop #1 on your pub crawl to get it out of the way. Another option is making a reservation for dinner, which you should do weeks in advance if possible, and enjoy some decent and overpriced German cuisine while taking in the surroundings. FYI, the Spiked Apple Cider and Holiday Smoothie are top-notch.

A Very Merry Christmas Guide to New York City | www.agreatbighunkofworld.com | A Great Big Hunk of World

Pete’s Tavern, 129 E 18th St, New York, NY

Just how many lights does Pete’s Tavern string across their ceiling during the holiday season? The world may never know. But what I do know is that you didn’t do Pete’s Tavern right until you’ve tried one of their Spiked Eggnog’s.

A Very Merry Christmas Guide to New York City | www.agreatbighunkofworld.com | A Great Big Hunk of World

Paddy Macguire’s Ale House, 287 3rd Ave, New York, NY

Paddy’s does very minimalistic holiday decor, but the tinsel-ordained shop-front and strands of tinsels, lights, and wood-working fireplace inside make this Irish pub seem like the perfect laid-back spot to finish off your year with a cold one, and a few of your closest friends.

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Molly’s Pub, 287 3rd Avenue, New York, NY

This pub, which looks as if it were plucked from the streets of Galway and dropped into New York City, also follows the less-is-more approach; but it’s still one of my favorite bars to visit during the holiday season. This spot doesn’t have an extensive holiday drink list, but after dropping over $10+ a drink at many other spots, it’s nice to kick-back with a more reasonably priced beverage.

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Lillie’s Victorian Establishment, 13 East 17th Street, New York, NY

While Lillie’s sticks to the typical train-style floor plan, it feels a bit more spacious than some others, though I’m sure there are nights where that isn’t the case. Being a bit further away from the other’s, this is a perfect way to end the night.

A Very Merry Christmas Guide to New York City | www.agreatbighunkofworld.com | A Great Big Hunk of World


Other Worthwhile Holiday Experiences

The Dyker Heights Christmas Lights, 11th Avenue to 13th Avenue and from 83rd to 86th Street
Nearest Subways: D,M

This Brooklyn neighborhood has received much acclaim for their awesome holiday displays. While some families go all out; one house used to have a small-scale moving ferris wheel being ridden by elves, some go a more simpler route, covering their entire home with 30,000 LED lights. Some displays even cost homeowners upwards of $15,000! I’ve recently seen tours being offered, because who wouldn’t want to bank off the popularity, but in all honesty, I’d recommend grabbing some hot chocolate from Dunkin Donuts and tackling the neighborhood on your own by either foot or car. You can book a guided tour of the Dyker Heights Christmas Lights here.

A Very Merry Christmas Guide to New York City | www.agreatbighunkofworld.com | A Great Big Hunk of World

Santacon, TBD
December 9, 2017

The first time I ever experienced Santacon, was freshman year of college while walking to work. You’d imagine my surprise when I was suddenly thrust into a cluster of what felt like 2,000 Santa Claus’s. Of course, I decided to take part in the nonsense the following year.

Santacon has become a popular pub crawl over the last few years in a handful of cities and involves dressing up as Santa (or a reindeer, or an elf, or in some cases Jesus, himself) and crawling from bar to bar, beginning around 10am. Usually, the only brunch is an excuse to day drink, but I guess Santacon can be added to that list. The price of admission, which gets you a wristband that usually allows for some discounted drinks gets donated to that year’s charity of costs.

As usual, Santa’s route isn’t released until decently close to the day of, but you can sign up for updates here. Santacon is not for the faint of heart, and those with anxiety of large groups may prefer a different activity.

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The Rockefeller Tree Lighting, 30 Rockefeller Plaza, New York, NY
December 4, 2019
Nearest Subways: B,D,F,M,1,6,N,Q,R

Each year, a tree is brought in from upstate New York and dropped in the middle of Rockefeller Center. The tree, which can sometimes average 94 feet tall and 56 feet wide has become a focal point for holiday excursions around the city. Live performances usually take place the day of the lighting from 7-9pm, followed by the lighting of the tree, which will remain lit until January 7th.

A Very Merry Christmas Guide to New York City | www.agreatbighunkofworld.com | A Great Big Hunk of World

Visit Santaland at Macy’s, 151 W 34th St, New York, NY
November 29 – December 24, 2019
Nearest Subways:B,D,F,M,N,Q,R,W

During my freshman year of college, I actually worked seasonally as an elf at Macy’s. After all, Santa’s real elves were busy back at the North Pole making gifts and Macy’s offers their elves a really nice hourly. It was always amazing seeing the excitement on the faces of children, not only when meeting Santa but during the entire experience. To make the wait a bit more tolerable, and just to add to the fun, the entire queue is designed to take you on a guided walk through the villages of the North Pole. After passing through the rock train that takes you to the North Pole, you pass magical snow globes, brilliant train displays, caroling snowmen, and more all before ever reaching the big guy. There’s also a couple cute photo ops along the way, which you can purchase along with your Santa photo once you’re done.

A Very Merry Christmas Guide to New York City | www.agreatbighunkofworld.com | A Great Big Hunk of World

The Macy’s Thanksgiving Day Parade, From 77th Street and Central Park West to Macy’s Herald Square at 151 W 34th St, New York, NY
November 28, 2019

Little fact about me; I was actually in the Macy’s Thanksgiving Day Parade from about age nine, to age seventeen when I finally aged out. As I always still wanted to remain a part of it, because to me the parade signifies the official start to the Christmas season, I join my grandparents each year as a make-up artist, helping to paint the faces of all 900 or so clowns you seen make their way down the parade route. It involves waking up at 3am, and by the time I get home, I usually crash as the parade replays on tv until dinner, but it’s always been one of my favorite parts of the year.

I’ve met dozen who’ve told me that they come all this way each year just for the parade, even lining up early in the morning despite how cold it may be that day. If you’ve ever gotten excited just seeing the parade on television, it’s a whole other feeling seeing it in person if you’re able. The parade concludes with Santa and Mrs. Claus making their way down the route in his sleigh, on his way to Macy’s where you’re able to meet him beginning the day after Thanksgiving.

Find out where to park your family by checking out the parade route here.

A Very Merry Christmas Guide to New York City | www.agreatbighunkofworld.com | A Great Big Hunk of World

The Holiday Train Show at the New York Botanical Garden, NYBG Main Entrance, 2900 Southern Boulevard, Bronx, NY
November 23, 2019 – January 26, 2029
Nearest Subways: B,D,4,2

Enjoy miniature New York landmarks as part of carefully put together train displays at the Holiday Train Show, located in the Bronx. Tickets run around $23-30 per adult and $10-18 for children 12 and under, but the show is definitely a great value for your money.

A Very Merry Christmas Guide to New York City | www.agreatbighunkofworld.com | A Great Big Hunk of World

See the Lighting of the World’s Largest Menorah, Fifth Avenue and W 59th Street, New York, NY
TBD
Nearest Subways: N,W,R,F

For a week straight, you can enjoy the lighting of this menorah which stands at about 32-feet tall and weighs close to 4,000 pounds. Over in Brooklyn, you can enjoy the lighting of a slightly smaller menorah at Grand Army Plaza, where you can enjoy a concert and latkes on the night or the first lighting.

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The Tree Lighting Under the Arch at Washington Square Park
Washington Square N, New York, NY
December 5, 2019
Nearesr Subways:A,B,C,D,E,F,M

The second longest-running tree lighting is right under the arch at Washington Square Park. For closet-singers, this a great time to let your inner star shine as Washington Square Park is one of the best spots for caroling. And at 5pm, enjoy the lighting of this 45-foot tree in front of one of the most popular backdrops.

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There’s no denying that New York City is one of the amazing cities for the holidays; and there is so much more to make your holiday merry and bright, like stopping by every holiday photo op such as the giant ornaments near Radio City Music Hall, or enjoying Christmas Eve Mass at St. Patrick’s Cathedral. But you’ll never be bored, and you’ll probably never experience a Christmas as magical as one in New York when it’s Christmastime again.

Recommended Tours

Christmas in New York with the Rockettes + Holidays Lights

New York City: 2-Hour Private Christmas Holiday Tour

oatmeal A Very Merry Christmas Guide to New York City | www.agreatbighunkofworld.com | A Great Big Hunk of World

25 comments on “A Very Merry Christmas Guide to New York City

  1. willsavefortravel

    Love this! We visited last year in early January so we missed a lot of these but I love the Christmas Tree at Rockefeller Plaza. It’s like quintessential Christmas to me!

    Like

  2. NYC is the best place to be at Christmas time. I have been lucky to see it once, and I would go back every year, at that precise time of the year. Your guide is amazing, I saw a tiny portion of all it features, but my favourite part was the shopping windows. Christmas markets – yeah, seen others around the world. But the shopping windows… Oh my, have never seen anything as everything as Christmas themed NYC shopping windows!

    Liked by 1 person

  3. silvia_romad

    Great article really enjoyed reading it! Christmas is the second best time to be in NYC after summer.

    Like

  4. Going to New York for Christmas an so, so excited!! This post is great and gives me an idea of where to start on our itinerary. I’ll definitely be looking back at this post multiple times over the next few months!!

    Kacie
    RegallySoled.com

    Like

  5. Momma To Go

    So I’ve lived in NY almost my whole life and I never actually done any of these! I mean i watch the parade and tree lighting on tv, and visit the tree each year, but I need to get on this! Now that my kids are old enough to some of these things. This year i have eyes set on Dyker Heights and the Christmas Spectacular!

    Liked by 1 person

    • I try to do both annually, and never get tired of em! Little heads up, there’s actually a Groupon deal on Christmas Spectacular tickets at the moment for great seats 😉

      Like

  6. I would love to hang around Bryant Park’s winter village and the Columbus Circle Holiday Market. For a night out, listening to Handel’s Messiah would absolutely be on my wishlist.

    Like

  7. I would LOVE to spend Christmas in New York, and your article has made me want to book my flights right now! Elf the musical sounds like so much fun… and I love looking at all of the window displays in the top department stores! If you like the displays at Bergdorfs and Lord and Taylor, you should check out the displays at Selfridges and Harvey Nichols in the UK 🙂

    Like

  8. This is such an awesome guide! It’s always been a dream to visit NYC at Christmas, I hope I can eventually make it, and with this guide I’ll certainly hit up all the best bits!

    Like

  9. Anuradha Goyal

    Wow, you make me feel everyone should at least once attend Christmas celebrations in New York.

    Like

  10. This is a lovely post. I am so fond of Christmas Carols. This makes me want to experience the Christmas celebrations in NY.

    Like

  11. Oh goodness, I am a completely NYC addict as it is and now I have to plan a Christmas visit to!!
    I have skated in the Central Park rink a couple of times in January but it’s not the same.
    We are coming to New York on Monday so I’ll drag my friends to Bryant Park for the market and ice rink there

    Like

  12. Wow – New York looks like THE city to visit for Christmas. Love this article and the photos too. I have spent the last three years in East Africa, and Christmas is pretty much the antithesis of the New York Christmas experience. I guess I will have to add this to my bucket list (and start saving up!)

    Like

  13. I love this guide!! I have done a ton of this stuff but not all of it. So I need to get some of this done. And boy do I semi remember Santacon. We used to do that allt he time. And super cool you were in the Thanksgiving Day Parade!!

    Like

  14. WOW. This is so useful — I have been thinking about a Christmas trip to NYC for the last couple of years and this post has moved it so much higher on my list! THANK YOU for putting this together. Bookmarking!

    Like

  15. Such a great read! Im actually headed to NYC next weekend and appreciated the tips!

    Like

  16. There is something magical about NYC during the holidays! Still haven’t seen the Macy’s parade, but hoping to do that soon.

    Like

  17. I’ve always wanted to visit NYC during Christmas. I have traveled to Buffalo, NY where my dad’s family lives during that time which is so close, but unfortunately unable to see NYC during the winter. It looks like such a beautiful city during that time of the year and so nostalgic with movies like Home Alone. Thanks for sharing this post!

    Like

  18. This makes me want to book a flight to NY right now! It is surely the best place to spend the holidays; so much going on!

    Like

  19. This is such a magical post! I would love to see the lighting of the tree as I am ice skating. I hate hoards of people but I feel like NYC is a MUST during the holidays!

    Like

  20. Lovely post! To start let me tell you that, as a fellow February girl, nop, that does not mean you love winter. I in fact hate it hahaha. But even though I do not like the cold, there is nothing like Christmas, and Christmas in New York have that “classy magic” that goes with the city all year long, but that it gets better around the holiday season! Thank you for sharing!

    Like

  21. I am swooning over this post! I legit need to go to NYC before the holidays and also side note: how fun does Santacon look?

    Like

  22. Oh yes! NYC is on my list during Christmas and this seems like a perfect motivation to make that trip into reality 😍

    Like

  23. What a well compiled list! I’ve always wanted to visit new york around christmas time, my dream is to ice skate at an outdoor rink!

    Like

  24. Pingback: Must-Try Bites at Bryant Park’s Winter Village | A GREAT BIG HUNK OF WORLD

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