Trip Ideas

9 Bucket-List Ways to Experience a Classic Christmas in New York City

As much as we love all the new and now happening in Manhattan throughout the year, sometimes, it's the most classic experiences that make it what it what it is—one of the greatest cities in the world, especially around the holidays. From legendary train shows to iconic ice skating to Radio City's world-famous Rockettes, here's how to enjoy the most wonderful time of the year in New York, New York.

See recent posts by Jetsetter Staff

Central Park Ice Skating

Ice Skating

When the mercury drops in New York each fall, a handful of parks and outdoor dining venues transform into ice rinks filled with bundled up tourists and locals. Head to Rockefeller Center for a quintessential New York skate session; the tree lighting ceremony is Dec. 4, and it will remain lit until midnight on Jan. 17, 2020. Bryant Park’s Winter Village provides unrivaled Midtown skyline views, but if you’re looking for some suds after skating, head to the Standard High Line in the Meatpacking District. Families should check out Central Park’s Wollman Rink; it offers youth figure and synchronized skating classes.


New York Botanical Garden Holiday Train Show

The New York Botanical Garden Holiday Train Show kicks off Nov. 23 and features more than 175 scaled New York landmarks crisscrossed by miniature G-scale locomotives chugging along almost a half-mile of track. Devised by Paul Busse and his team at Applied Imagination, this microcosm of the Big Apple is an architectural masterpiece and is constructed out of natural materials such as leaves, bark, acorns, and cinnamon sticks. This year, the display spotlights Central Park and its iconic sights including Belvedere Castle, Bethesda Fountain, and NYBG's own Enid A. Haupt Conservatory—not to mention world-famous city landmarks like the Chrysler Building, the Brooklyn Bridge, and the Statue of Liberty. Certain Friday and Saturdays in December are dubbed “Bar Car Nights,” where each ticket includes after-dark admission to enjoy specialty cocktails, DJ sets, artistic ice carving, festive performances, and more.


Department Store Holiday Window Display

The frenzied holiday shopping season is fast approaching and while some of New York’s biggest retailers are getting ready to slash prices, they’re also hard at work on putting together intricate holiday window displays, each with a different theme. The big players include Macy’s Herald Square, Bloomingdale’s, Bergdorf Goodman, Tiffany & Co., and Saks Fifth Avenue; last year’s standouts included themes such as "Dr. Seuss' The Grinch" and "#BergdorfGoodies, " which was inspired by holiday sweets.

People visiting Christmas Market stands in Union Square in Midtown Manhattan.

Union Square Holiday Market

From Nov. 21 through Dec. 24, UrbanSpace’s Holiday Market sets up shop in Union Square, with over 100 booths designed to mirror the traditional pop-up shops in Northern Europe. Spend an afternoon picking up gifts for your friends and family (or for yourself); some trinkets you can expect to find are holiday-themed crafts, ornaments, handmade jewelry, bags, and blown glass houseware.


Radio City Christmas Spectacular

Watch the Rockettes dance in perfect unison (including their signature high line kick) at the Radio City Christmas Spectacular. The show is set to include a mesmerizing 3D ride with Santa, from the streets of New York City to the North Pole, as well as ice skaters, dancing teddy bears, and a living Nativity.


Tea Time at the Plaza

The crown jewel of the fabled Plaza Hotel, Palm Court served as a setting for scenes in The Great Gatsby, and its ornate stained glass ceiling and stately columns exude a grandeur and charm that have been wowing guests since its opening in 1907. In true Plaza fashion, the holiday decorations here are elegant and timeless. Take a break from shopping and stop in for afternoon tea (we recommend the New Yorker or Eloise varieties).


Guggenheim Rotunda Holiday Concert

Get in the holiday spirit this December at the Solomon R. Guggenheim Museum. Pulitzer Prize-winning composer Caroline Shaw, eight-voice ensemble Roomful of Teeth, and the three percussionists of Tigue will come together to spread the holiday cheer with a performance in Frank Lloyd Wright’s beehive-shaped rotunda on Dec. 15 and 16 at 7 p.m. Tickets sell out quickly so be sure to book in advance: prices for floor seating are $55 for members, $60 for adults; prices for ramp seating are $20 for members; $25 for adults.


The Nutcracker by The New York City Ballet

One of the most classic holiday experiences in The City That Never Sleeps is seeing a performance of George Balanchine's The Nutcracker, which is put on by the revered New York City Ballet and runs from Nov. 29 through Jan. 5, 2020. Admire the poise and talent of the show’s 90 dancers and 62 musicians as you’re transported to a fantasyland of nutcrackers, toy soldiers, giant mice, and handsome princes.

Homes with Christmas Lights in Dyker Heights neighbourhood of Brooklyn, New York, USA.

Dyker Heights Christmas Lights, Brooklyn

For something a bit different, make your way to Brooklyn’s Dyker Heights, where Christmas decorations are on steroids. This predominantly Italian-American section goes all out for the holy holiday; houses are tricked out with over-the-top ornamentations like gaudy lights, 30-foot toy soldiers, animatronic toys, and motorized displays. See just how seriously this nabe takes decorating by booking the Christmas Lights Tour from Dec. 1 to Dec. 31 (except the 24th and 25th), which lasts approximately 3.5 hours, and just be glad you’re not paying their electric bill.

Want more?



All products are independently selected by our writers and editors. If you buy something through our links, Jetsetter may earn an affiliate commission.