The Ultimate Holiday Guide to New York City

Whether you're local or visiting, here's where to spend the festive season

December 12, 2023 6:36 am
Christmas in the Big Apple
Christmas in the Big Apple
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It’s the most wonderful time of the year, but for New York and its visitors, it can be the most overwhelming time of the year to comb through hundreds of holiday-themed events and narrow down which are worth a spot on the itinerary. But as the only person who can rival Mariah Carey’s love for Christmas (she can squeeze into a pair of red leather tights and hit all the notes in “O Holy Night,” after all), I’m here to help with a comprehensive list (that I’ve checked twice) of seasonal must-sees around the Big Apple. From bars and restaurants to shows and outdoor experiences, one thing’s for certain: we all must have been really good this year to get this much festive variety. Check out my recommendations below to plan the ultimate big city winter escape. 

The Bars and Restaurants

Rolf’s gets all of the love and attention, especially on social media, for its tinsel and ornament-lined ceilings. And while it’s a space you have to check out once in your lifetime, there are a handful of other gastronomical experiences and pop-ups that should top any travel list. Quirky and ornate Oscar Wilde, known for its thematic cocktails featuring mezcal and tequila, looks like a scene from Santa’s study with Christmas trees, stockings and oversized bows. PHD Terrace at Dream Midtown showers its guests in canopied lights at its rooftop winter wonderland, dubbed Midwinter Night’s Dream. 

Block-long La Grande Boucherie offers a cozy backdrop to Sunday brunch with classic French dishes like steak tartare and escargot, though you should save room for a slice of Breads Bakery’s famed chocolate babka to enjoy as you meander down Fifth Avenue and relish the impressively intricate department store window displays. 

All of that said, at the end of the day, Christmas is all about tradition. My friend Anthony and I visit the Rockefeller Christmas tree every year, snap a few photos and then zig-zag our way through the crowds to get to Ocean Prime — a timeless and luxurious Midtown haven with dirty Martinis, custom-built shellfish towers, steaks and a warm butter cake that always steals the show. It may typically be a place to take someone on an important business lunch, but it’s our home base to cheers to the official start of the holiday season. 

The New York Botanical Garden Holiday Train Show
New York Botanical Garden Holiday Train Show
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The Great Outdoors 

Bronx and Brooklyn’s botanical gardens are the two largest and most popular in the city, and they both offer wonderful outdoor holiday experiences. The former, located just off the Metro North’s Harlem line, is home to the beloved Holiday Train Show, a 30-plus year tradition that features nearly 200 scaled and iconic NYC buildings and more than 25 model trains and trolleys. A step outside will lead you to its NYBG Glow installation, a holiday light show in its fourth year that wows spectators with thousands of choreographed bulbs in different shapes and colors. The latter hosts a series called Lightscape which, like Glow, displays an avalanche of glittering lights, except this set-up takes visitors on a curated, multi-sensory trail that highlights the property’s sculptures, water features and moments of site-specific music and sounds. 

While in Brooklyn, a trip to Dyker Heights is also a must-see to observe some of the country’s most over-the-top and impressive home decorations. But if you’re limited to Manhattan, simply set aside some time to enjoy one of its many ice skating rinks (Central Park’s Wollman Rink is a personal favorite because of its larger size) and fresh air that isn’t tainted by taxi exhaust or unidentifiable sewer smells. 

The Christmas Spectacular
The Christmas Spectacular
The Rockettes

The Shows 

The Christmas Spectacular, featuring the Radio City Rockettes, is an obvious choice, as well as any touring musical act with holiday-themed shows (this year brings in stars like Mariah Carey, Brett Eldredge, Darren Criss and Il Divo). There are also a few other entertainment standouts worth considering. 

Cirque du Soleil has added a little jingle to its signature acrobatics with its first-ever holiday production, ‘Twas the Night Before. Created especially for families, the Madison Square Garden spectacle touts flips, twists and an original soundtrack to complement the story of a girl in search of a little Christmas magic. For a more spiritual departure, the New York Philharmonic’s performance of Handel’s Messiah is an audio masterpiece, playing all two and half hours of its iconic melodies from start to finish for four evenings. The organization also streams its musical event online for anyone who can’t join in person. 

You also can’t go wrong with any interpretation of The Nutcracker. This year includes George Balanchine’s rendition at the New York City Ballet, Keith Michael’s rendition at the New York Theatre Ballet, Company VIX’s Nutcracker Rouge burlesque show and Frances Patrelle’s 25th anniversary of The Yorkville Nutcracker

But if you find yourself on Santa’s Naughty List and have outgrown the tragedy that is SantaCon, Santa’s Secret in Hudson Yards combines craft cocktail imbibing with naughty cabaret performances set in a vintage speakeasy environment. Combining the words “sexy” and “Christmas” may not have been on your holiday bingo card, but it’s bound to become your new favorite NYC tradition. 

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The holiday market in Bryant Park
The holiday market in Bryant Park
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The Markets 

Though you can find most of the same stuff at every NYC holiday market, the vibes and highlights vary at each locale. Winter Village at Bryant Park has quickly emerged as the go-to destination for tourists considering its iconic ice skating rink (with bumper cars!) that is, frankly, more manageable than the chaos at Rockefeller Center. It’s also bordered by a number of shops and food stalls — more than 180 to be exact — so that you can tack on any last-minute gift-buying after partaking in some good old-fashioned holiday cheer. 

But don’t overlook the intimidatingly busy Union Square Holiday Market, which transforms its uber-popular Greenmarket into a winter wonderland with 160 local and national vendors selling everything from fragrances and home goods to jewelry and Bavarian pretzels. Most purchases also support small businesses and charitable initiatives since it’s the season of giving, after all. 

Other highlights include Urbanspace at Columbus Circle for its handmade items, Upper West Side’s Grand Holiday Bazaar for its antiques, Hester Street Fair at The Seaport for live music and the Brooklyn Navy Yard for its enormous selection of offerings in a 100,000 square-foot retail space. 

Holiday light display at McGraw-Hill Building on Avenue of the Americas at 48th Street
Holiday light display at McGraw-Hill Building on Avenue of the Americas at 48th Street
Getty Images

The Spirit 

No matter how you decide to plan your trip, there’s an undeniable spirit in the air that makes New York one of the most sought-after destinations around the holidays. And while such a statement sounds like it was plucked straight from a cheesy Hallmark movie, it won’t feel hyperbolic after immersing yourself in the seasonal sights, sounds, thrills and tastes that the country’s most festive city has to offer.


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