Even when the streets are crammed with tourists and icy wind pierces the air, New York City is always worth a visit, especially during the holiday season. With five boroughs — counting Staten Island — and over 300 miles to cover, there’s a lot to see and do, but where should you start? Massive trees hauled in from upstate New York and rows of candy canes kicking with iconic precision may dance in your head, but we have some alternative sights to add to your list of must-sees, most of which you probably wouldn’t know about unless a native told you. You’re welcome!
It doesn’t matter whether you’re planning a staycation or traveling from Kansas, there are some steps you must take before hitting 5th Ave or the Brooklyn Bridge running. First, pack your bags. We didn’t consult every New Yorker for this story, but we can tell you they’d all agree a portable charger, warm scarf you can wrap around your neck at least three times, and easy-to-carry bag that can fit said portable charger are necessary. Although we’re not traveling very far, we’ve already got our Burberry Narrow Check Cashmere Scarf, Small Knight Bag, and, for those below-freezing days (because they will come), Check Wool Hot Water Bottle ready to go. Do you?
Next consult our guide, which features everything from candlelit concerts to winter solstice campfires to Kwanzaa celebrations. Ahead, a (somewhat) comprehensive guide to spending the holidays in New York City.
Don’t Ignore the Parks
Those who like to wander will find sanctuary in Central Park, an uptown oasis where a skating rink, duck pond, and carousel await. There aren’t many places that make you feel like you’ve stepped into a Currier and Ives print, but Wollman Rink, located near the famous Gapstow Bridge, is one of them. There will be a lot of people, but not so many that you’ll lose breathing room on the ice. No matter what you’ve seen in TV shows and movies, feeding the park wildlife is strictly prohibited, but that doesn’t mean you can’t admire the ducks from afar. Technically, the historic carousel is in the Children’s District of the park, but no one really outgrows the ride, so consider making a stop there, if your legs need a break from all that walking. Merry-go-rounds make you nauseous? Take the two-minute walk to the Chess and Checkers House to see if your gambit is clever enough to beat one of the local masters.
When in dire need of some holiday spirit, walk to the Harlem Meer in the northern part of Central Park. There, as if by magic, lit Christmas trees float in the lake. Further downtown, you’ll find Sutton Place, where the conservatory’s third annual holiday sing along will commence. After all, the only way to spread holiday cheer is singing loud for all of “Little London” to hear. But when it comes to celebrating everything the holidays have to offer, the Marine Park Alliance in Brooklyn always does it right by honoring the winter solstice and also Kwanzaa on December 26. Remember that hot water bottle? It’ll come in handy while hiking through Van Cortlandt Park with NYC Parks Urban Park Rangers who will finish off the day with a celebratory campfire in anticipation of the upcoming spring equinox.
Embrace the City’s History
New Year’s Eve may be overrated, but staying in New York to ring in 2024 is not, especially if you spend the weekend at the historical Apollo Theater experiencing its annual Kwanzaa celebration. When in need of something more low-key, especially if you’re a resident hosting out-of-towners, consider grabbing dinner at Fraunces Tavern near Bowling Green. It’s incredibly old and historic — it even has its own museum — but that’s not the only reason we like it. No, it’s the cozy, decorated interior that keeps us coming back for more. After that, grab a drink at Whiskey Wonderland, the holiday pop-up at Great Jones Distilling Co.. It’s not old, but it is the city’s first whiskey distillery. Or sneak down the steps to the Back Room in the Lower East Side — brave the darkness of the building’s back alley, where, on the right, you’ll find one of the only speakeasies from Prohibition left in New York City.
Most of the functioning hideaways from that era no longer exist, but their demise helped give rise to the city’s sprawling jazz scene. Today, you can find a club in almost every neighborhood. The Village Vanguard — the “most famous basement in New York City” — opened in the late ’30s and continues to be a hotspot for shows today. A slightly more upscale option, Dizzy’s Club, can be found on the west side at Lincoln Center.
See a Show You Can’t Anywhere Else
Award-winning tribute artist Peter Mac is spending this December bringing Judy Garland back to life. Not seeing his entertaining homage to Garland’s legendary 1963 CBS Christmas special would be a mistake. Gossip Girl fanatics will appreciate the recent extension of the Mckittrick Hotel’s Sleep No More, an interactive performance of a Shakespearean tale, which officially concludes its 13-year run in 2024. Maybe you’ll be the one lucky guest taken to the elusive sixth floor — not even we really know what’s up there. While Sleep No More is sexy in a frightening way, Candlelight Concerts offer up the romance missing from those bloody bath scenes. Like the name suggests, these concerts take place amid a sea of battery-operated LED candles that flicker for an hour as a musical ensemble fills the venue with a variety of sounds, spanning a range of genres, including jazz, pop, and movie soundtracks.
Explore the Holiday Markets
Holiday markets — specifically those in Union Square and Bryant Park — will be crowded, but even natives, and the arbitrary scrooge, will say browsing the hundreds of vendors is a rewarding tradition. Leaving Manhattan? Visit the Black Girl Magic Street: Winter Artisan Market, which kicked off the first week of December in Bed-Stuy, but will continue each weekend through the month. This winter village includes a curation of Black-owned brands, art, and live music. It’s nearly impossible to walk away without a gift. The Astoria Market at Bohemian Hall lives about seven miles north. On December 17, it transforms into a full-blown holiday party featuring handcrafted gifts and a “Grandma’s Kitchen” menu. Friendly warning from us to you: Don’t tell your actual grandmother if the apple strudel at the market is better than hers — she might actually put coal in your stocking.
Never Miss Any Take on The Nutcracker
The New York City Ballet won’t continue its performances of The Nutcracker until the new year, but you can catch New York Dance Theatre’s take on the story the weekend before Christmas, a performance that’s taken place since 1982. As a part of New York Theatre Ballet’s Once Upon a Ballet series, comes Keith Michael’s Nutcracker, a show best suited for children, although we’re just as enthusiastic about the owl that reportedly flies over the audience. Anyone in search of a more nontraditional show should consider getting tickets to the Brooklyn Nutcracker at Kings Theatre on December 16. No plans for Christmas Eve eve? The Hip Hop Nutcracker, another modern version of Tchaikovsky’s ballet, can be seen at Prudential Hall in — don’t hate us — New Jersey. It’s worth the PATH ride.
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