Holidays in the Big Apple: A Field guide to Celebrating!
Ah, New York City during the holidays—where dreams of sugarplums meet the harsh reality of elbowing a tourist in the stomach to get a decent photo of Rockefeller Center’s tree. But fear not, intrepid urban elf! I’ve curated a list of merry misadventures to sprinkle some peppermint-flavored pizzazz into your yuletide season.
Explore Hidden Winter Wonderlands!
The Rooftop at Pier 17 Winterland: Skating on Top of the World
Whoa! Manhattan’s only roof-top skating rink make you feel like you’re gliding into the skyline itself! Panoramic views of the Brooklyn Bridge and the Statue of Liberty? Check. Cozy dining cabins straight out of a Hallmark movie? Double check. If you’ve ever wanted to experience the sheer joy of a rom-com montage without the pesky subplot, this is your moment.
Where Pandas Glow, Dragons Dazzle, and Holiday Magic Goes Full Wattage! Tianyu Lights Festival is no ordinary light show—it’s a luminous holiday playground where imagination runs wild. Stroll past fantastical light displays, hop aboard the whimsical magic rides (yes, they shine too!), and meander through a festive marketplace bursting with artisanal goodies and holiday treats. It’s part fantasy, part Instagram gold, and all the excuse you need to say, “I came for the lights but stayed for the cider.” A holiday outing so electrifying, even your holiday spirit will get a recharge.
A Jolly Good Time: Your Guide to NYC’s Most Ridiculously Festive Shenanigans
If Christmas spirit were measured in cocktails and questionable decisions, New York City would be the North Pole—and you, my dear reveler, are Santa Claus. Let’s dive into the holly-jolly madness.
Ho Ho Ho! The Santacon Sleigh Ride!
For Santacon shenanigans on December 14th, start at the East Village’s Barcade, where craft beers flow like holiday cheer, and retro arcade games transport you to a simpler, joystick-filled time. Feeling peckish? Head to Crocodile Lounge, where every drink comes with a free pizza—a carb-laden survival kit for navigating Santa’s spirited chaos. If you’re venturing to Hell’s Kitchen, Cantina Rooftop offers festive vibes and stunning skyline views, proving that even Santa deserves a margarita with a view. As Santacon routes are always in flux, check the official Santacon NYC website or app for the latest bar updates before suiting up in your finest red velvet. Cheers!
NYC Christmas Karaoke Night: Where Your Inner Mariah Carey Awaits!
If the thought of singing with a room full of drunk strangers doesn’t jingle your bells, grab a few friends and head to Gagopa Karaoke in Koreatown. Their cozy private rooms let you belt “All I Want for Christmas Is You” with only your nearest and dearest judging your high notes. Feeling braver? Swing by Sing Sing Karaoke in the East Village, where the festive crowd turns “Jingle Bell Rock” into a group therapy session (or a shared descent into musical chaos). Whether you’re a vocal virtuoso or a toddy-fueled tenor, it’s a holly-jolly way to unleash your holiday spirit.
So, throw on that sweater, grab a mic, and join the Santa horde—it’s the most wonderful (and weird) time of the year!
Feeling festive and daring? Join Santacon, where thousands of grown adults dress as Santa and stumble through the city fueled by questionable eggnog and poor life choices. If you’re more into visual chaos than participatory, find a discreet coffee shop to spectate—it’s the North Pole meets “The Hangover.”
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Naughty & Nice Shopping Gift Guide!
Find the Perfect Gift at these Quirky Holiday Markets
Looking for gifts that scream thoughtful, but also, WTF?!? Try Wildcard Taxidermy, where you can snag a taxidermy mouse playing cards, Victorian mousetail earrings – or a skull or two (don’t ask whose) at Myhalia Studio. For the chic and quirky crowd, Artists & Fleas delivers with handcrafted leather goods, vintage treasures, and “I swear this is one of a kind” jewelry. When your festive vibe requires refueling, stop by Rolf’s German Restaurant, a twinkling, ornament-stuffed Christmas wonderland where you might not be able to see the person you’re eating with through the garlands.
Need more ideas? Swing by Canal Street Market for a mix of indie brands and small-batch goodies that practically beg to be Instagrammed. Or brave the crowds at Chelsea Market’s Holiday Pop-Up, a labyrinth of seasonal delights where you’re just as likely to find artisanal chocolates as funky home decor. And if you’re really looking for the perfect blend of art and oddity, Brooklyn Flea serves up rare vinyl records, antique curios, and “conversation starter” furniture.
For the person who has everything (or worse, shops for themselves right before Christmas), these markets offer gifts they didn’t even know they wanted—because let’s be honest, no one impulse buys a Victorian medical tool for themselves.
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Offbeat Holiday Show That’ll Deck Your Halls!
“The Nutcracker Rouge“ – Tchaikovsky’s classic meets a risqué twist in this burlesque reimagining. Think fewer sugarplums and more cocktails – and an audience wondering if “The Dance of the Sugar Bum Fairy” was always meant to be this… cheeky.
The hilariously risqué Nutcracker Rouge by Company XIV is the reimagined Nutcracker you didn’t know you needed. This sensual burlesque show takes place at Théâtre XIV, located at 383 Troutman Street in Bushwick, Brooklyn. Known for its lavish mix of circus artistry, ballet, and sultry cabaret, the performance runs through January 27, 2025, making it a perfect alternative holiday outing for adventurous adults. Expect spellbinding aerial acts, seductive choreography, and plenty of holiday spice in this over-the-top production. Note: it’s strictly 21+, and tickets are available in various tiers, from standing room to champagne upgrade
Whether you’re naughty, nice, or just need a break from the umpteenth New York Ballet rerun, the “Nutcracker Rouge” puts the extra in extraordinary this holiday season.
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Offbeat Activities in Iconic Locations
Holiday Jazz at Dizzy’s Club
It’s jazz but make it jolly. Head to Dizzy’s Club for a holiday-themed set that blends bebop with “Jingle Bells,” all while you sip cocktails in a room with panoramic views of Central Park. Think smooth saxophones, cozy vibes, and a chance to feel sophisticated—even if you’re humming along off-key.
Coney Island Polar Bear Club Swim
Who needs chestnuts roasting when you’ve got toes freezing? On New Year’s Day, the fearless (and possibly frost-resistant) Polar Bear Club plunges into the icy Atlantic at Coney Island. Whether you’re braving the waves or cheering from the shore with a thermos of cocoa, it’s the perfect way to combine adrenaline and holiday cheer. Plus, it gives “dashing through the snow” a whole new meaning.
Get Artsy and Creative
Holiday Wreath-Making Workshops
Channel your inner artisan by creating a festive wreath at the New York Botanical Garden. Their workshops provide all the greenery and flair you’ll need to craft a masterpiece—no green thumb required! For another option, check out sessions in Brooklyn via ClassBento, where you can sip and snip your way to a bespoke holiday decoration (New York Botanical Garden, ClassBento).
Christmas Cookie Decorating Classes
Elevate your frosting game at Milk Bar or Magnolia Bakery, where hands-on workshops teach you to transform simple cookies into edible holiday art. Plus, you get to devour your delicious creations afterward—crafting has never tasted so sweet (Milk Bar, Magnolia Bakery).
Cozy and Unique Outdoor Adventures
Dyker Heights Lights Tour: Embrace Brooklyn’s most extravagant tradition with a guided walking tour of Dyker Heights. Learn the bizarre, charming backstories of its dazzling displays, from oversized Santas to synchronized twinkling lights. Leave the parking woes at home and let someone else lead the way (Dyker Heights Tour Info).
Horse-Drawn Sleigh Rides in Prospect Park: For the romantics or families seeking a Hallmark moment, bundle up and glide through the wintry charm of Prospect Park. This experience makes for perfect holiday photos (and lots of warm cocoa afterward).
Festive Kayaking on the Hudson: Yes, kayaking in December! For the thrill-seekers, look for holiday-themed paddle sessions on the Hudson. Bonus: those brave enough earn serious holiday bragging rights.
Happy holiday adventuring!
