How To Do Christmastime in NYC Like a Pro

Christmastime in New York City!! It really IS the Most Wonderful Time of the Year!  I absolutely love the holiday season and I love being in the city to celebrate.

Without further ado, here are my favorite ways to get festive this winter in NYC! And expect further details on many of these activities as the holiday season continues.

Look at Festive Things


Everyone MUST go see the Rockefeller Center Christmas Tree. Yes, it will be VERY crowded and NO, I wouldn’t advise bothering to join the crowds ice skating down below. But you must see the tree if you truly want to celebrate Christmas in New York. If you’re really feeling brave, come by for the official tree-lighting on Wednesday, November 28th. Otherwise, I recommend doing a fairly quick stop over - day or night - en route to viewing the beautiful holiday windows along Fifth Avenue. No matter when you go, it WILL be crowded.



Right near Rock Center and the tree, don’t miss the windows at Saks or Bergdorf Goodman - both Fifth Avenue luxury department stores curate gorgeous holiday displays every year. As you walk up Fifth Avenue from Saks to Bergdorf, you’ll see plenty more festively dressed windows (and crowds). For example, each December the Cartier Flagship Mansion gets decked in a huge red bow.

Bloomingdale’s 59th Street holiday windows went up very early this year and we got a peek. The windows are Grinch themed and include displays asking you to show your “Resting Grinch Face” and to karaoke with the Grinch. Inside Bloomies, there’s also “ice” skating in the Ralph Lauren Men’s Department and human-sized snow globes and gingerbread houses to celebrate the season. 

Macy’s in Heralds Square also does a great window display each Christmas - but more on that location later.


In the Bronx, each holiday season, the New York Botanical Garden delights thousands of visitors with their world famous Holiday Train Show. Timed entries to the show are offered daily from November 17th through January 21st. Guests of all ages will enjoy seeing the beautiful working toy trains intermixed with plant life and NY-centric scenery. My favorite part of the show is spotting all the models of famous New York City buildings.


Beginning the evening of November 27th and going through January 4, 2019, visit Luminaries, a gorgeous multi-colored canopy of suspended lanterns in the Winter Garden at Lower Manhattan’s Brookfield Place. Light shows will play every half-hour throughout the day from 8am until 10pm (excluding November 30th after 3pm through December 2nd and all day December 9th).

And from 10am through 8pm daily, guests can send a wish to the lanterns via three touch-activated “Wishing Stations” that will cause the lanterns above to magically change color. For every wish sent up during the holiday season, Brookfield Place will donate $1 to Little Essentials. The installation will kick off at 5:30pm on Tuesday, November 27th with a “Light Up Luminaries” show.


If MEGA Christmas light displays is what you’re after, head to Dyker Heights, Brooklyn for the neighborhood’s famous holiday light displays (aka Dyker Lights). For the past 30 years, about 100,000 visitors per season flock to this section of Brooklyn in the month of December to gawk at the over the top Christmas light and decorative displays put on by homeowners in the area. Many houses shut off their lights around 9pm so aim to arrive on the earlier side to ensure you’ll see everything and to get a head start on the massive crowds. We’ll be there next month to check it out and I can’t wait to report back!

See a Festive Show


The mother of all Christmas shows is right in our backyard - The Radio City Rockettes Christmas Spectacular. It’s a must do activity at least once in a childhood, but since tickets are fairly pricey, it’s probably best to wait until your kid reaches at least age 5 to attend. Performances are offered daily from November 9th through January 1st. Catching a performance and then walking over to Rock Center to see the tree and then to Fifth Avenue to see the holiday windows is a perfectly spent NYC holiday day.


If ballet dance is more your speed, the New York City Ballet’s Nutcracker is also a holiday must. Even if you’re not a ballerina, go for the breathtakingly beautiful costumery and overall elegance of the performance and Lincoln Center generally. Performances begin on November 23rd and run through December 30th. This 2 hour experience is best suited for older children who can sit still and be quiet for the full show.  


I’m also really excited about the touring Dr. Seuss’ How the Grinch Stole Christmas Musical because, this year, the Grinch will be played by the amazing Tony-nominated Gavin Lee, whom we just saw knock it out of the park as Squidward in SpongeBob the Musical! The show will be at MSG’s Hulu Theater from December 13 through 30th. While younger kids *could* be frightened by the title character, this show, compared to the other two options mentioned above, is appropriate for all ages.

Have a Festive Meal or drink


Make a reservation ASAP for a holiday lunch at Rolf’s, an old German restaurant in Gramercy Park that leaves its insanely ornate holiday decor up through May of each year. The extremely festive ambiance is just perfect to get you in the holiday mood. Last year, I probably reserved our table in October and managed to snag a prime time reservation for a Saturday in December.


This is one of many “Miracle” Christmas themed cocktail bar pop-ups set to open across the US and Canada this season. Miracle on 9th has been kicking it on East 9th Street for a few holiday seasons now and the reviews are mixed. Even if it’s not the best service or drinks you’ve ever had, I honestly don’t think I could be too unhappy boozing in a bar with festive Christmas decor. Miracle on 9th will be open November 23 through December 31 from 4pm until 2am on weekdays and 2pm to 2am on weekends.


At the Plaza Hotel, you can have Tea with Eloise in the Palm Court daily between noon and 4:45pm this holiday season. The menu of sandwiches, sweats and teas or cold lemonade is $60 per child.


And over at the posh Carlyle Hotel, you can ogle over Ludwig Bemelman’s famed Madeline murals while enjoying a chi-chi Madeline’s Tea every Saturday from December 1st to December 29th at 10:15am or 1pm. The cost is $80 per person ($40 for children under 3 years old).

Shop for Festive Gifts


The weather is usually still perfectly crisp and warm enough in November and early December to be outside. On one such nice day or early evening, it’s lots of fun to roam through one of the three Urbanspace Holiday Markets that pop up in Manhattan during the holiday season. Located in Columbus Circle, Bryant Park and Union Square, these markets feature artisan merchants selling festive gifts for your holiday shopping list and all kinds of delicious eats to give you the fuel you need to shop.

My favorite of the three markets is the one in Bryant Park because that park is also home to the Bank of America Winter Village this time of year. The Winter Village includes a FREE pop up ice skating rink and rink-side food court called The Lodge.

If checking out the Columbus Circle Holiday Market, don’t skip the beautiful Holiday Under the Stars display at the Shops at Columbus Circle, featuring Swarovski crystal illuminated and color changing stars hung from the ceiling of the indoor shopping complex’s lobby area.


If you’re a commuter or crunched for time, check out the Grand Central Holiday Fair in Vanderbilt Hall. The shopping gets going there beginning on November 12th and lasts through Christmas Eve. And if your kids need bribing, visit the FREE Holiday Train Show at the NY Transit Museum Annex while you’re there.



New York’s most iconic toy store is BACK. FAO Schwarz will reopen its doors on November 16th, this time in smaller digs right near to the Christmas tree in Rockefeller Center. Expect it to be mobbed during the holiday season.


And if you prefer brand new to historic icons, consider visiting Camp, a new retail chain set to open its first store in mid-December at 110 Fifth Avenue.  Camp will feature toys, clothing, gifts and an on-site Milk Bar, combined with play time and interactive experiences. Best of all, Camp will change its overall look and merchandise every 8-12 weeks.

Visit the Most Festive Guy I Know at Macy’s Herald Square Santaland

Sure there are Santa sightings all over the city (Ugh SantaCon) but the real Santa(s) live at Macy’s Santaland! I grew up visiting Santaland as a child, so it will always hold a special place in my heart. Even if it’s brand new to you, the Macy’s Herald Square flagship store  is wonderful around the holidays.

The entire 8th floor of Macy’s Herald Square (151 West 34th)  is transformed into a winter wonderland, culminating in a FREE visit with Santa that is like no other. In the past, the lines to meet Santa here could get atrocious, but Macy’s now requires advanced reservations. Set your alarm clocks for November 18th when reservations go live. Santa is only accessible by advanced reservation for a pre-set time slot.

Guests can join the line for Santa at their reserved time. And don’t worry, there are plenty of festive landscapes to enchant you while you wait. The path toward Santa is filled with beautiful holiday displays known as Santaland Village. If you’re in a rush, Macy’s now offers an express line directly to Santa Fridays through Sundays (but I think this misses most of the fun).

As mentioned, visiting Santa is totally free, however professional pictures are available for purchase beginning at $20.99 a package. Macy’s will also do their best to have your children meet a Santa that best matches their cultural background. Just mention this request to any elf you see.

Wishing you the happiest of holidays!