Holiday Fun

31 Nice and Naughty Ways to Celebrate the Holidays All December Long

Every day during the holiday season can be a holly, jolly one.

Photo courtesy of Showfield

You set calendar alerts for the arrival of peppermint mocha season at Starbucks. Mariah Carey’s best album has been on repeat since Halloween. You’ve seen the Radio City Rockettes kick over their heads dozens of times. It’s official: You’re obsessed with the winter holidays.

Second only to the North Pole, New York is the merriest place to be during the holidays. Here’s where to deck the halls, sing some carols, light Hanukkah candles, and feel the Christmas spirit until the last of the Yule log burns. 

1. Practice your triple axles on a frozen tarmac at the TWA Hotel, and then perhaps canoodle in the heated pool-cuzzi afterward

2. Reminisce (and feel a bunch of secondhand embarrassment) over horrors of holidays’ past at Otto’s Shrunken Head‘s holiday-themed comedy storytelling night on December 2.

Photo courtesy of Otto’s Shrunken Head/Facebook

3. Attend some charming Christmas tree lightings—aside from the main show at Rockefeller Center. The Seaport kicks things off on December 2; Harlem will be holiday hopping on December 4; and Madison Square Park and Dumbo get lit on December 5.

christmas in new york
Photo courtesy of Rockefeller Center/Facebook

4. Roller-skate with Santa at Dreamland Roller Rink’s pop-up location at City Point.

5. All drag queens BenDeLaCreme and Jinkx Monsoon want for Christmas is your attention—so give it to them at Town Hall on December 11.

bendelacreme jinkx monsoon christmas in new york
Photo by Matt Baume/Courtesy of BenDeLaCreme + Jinkx Monsoon’s All I Want for Christmas Is Attention

6. Join a holiday sing-along with a few of NYC’s top performers: self-proclaimed country queens of Christmastime the Sweetback Sisters in Brooklyn; funky vocalist Brianna Thomas in Harlem; and Broadway’s Norm Lewis in midtown.

7. See all of the Nutcrackers—a hip-hop version at Kings Theater, Company XIV’s Nutcracker Rouge, Dorrance Dance’s jazzy take at the Joyce, and the conventional version at New York City Ballet.

8. Eat a different kind of Navidad dinner with stew-y tamales, brioche speckled with ham, and rich flan, courtesy of Venezuelan chef Mercedes Golip. Greenpoint cookbook shop Archestratus hosts this special feast on December 7.

Photo by Patrick Dolande/Courtesy of Archestratus Books & Foods

9. Who could possibly “bah humbug” at seeing A Christmas Carol? Tony Award–winning playwright Jack Thorne’s take on the Charles Dickens classic is earning raves at the Lyceum Theatre and plays through January 5.

10. A little more under the radar but just as worthy of your time is the Merchant’s House Museum’s version. Sending you straight back 150 years to the Victorian era, this immersive reading is derived from Dickens’s original 1867 script.

Photo courtesy of Merchant’s House Museum

11. Check out the tall and glorious lights of the world’s second-largest Hanukkah menorah, December 22–30! (Or the largest, if you want to be a snob about it.)

12. Wow, A Charlie Brown Christmas looks good for 52! Listen to the Christmas special’s timeless score, courtesy of the Cyrus Chestnut Quartet, at Columbia University. 

13. Celebrate the holidays like you would in Santa’s hometown—yep, he didn’t always live in the North Pole; was born and raised in Rovaniemi, Finland—with glogg at Bed-Stuy’s Skal, Julbord at Aquavit, and a ball at the American Scandinavian Society.

Photo courtesy of Aquavit NYC/Facebook

14. Live out your Big dreams and splurge on a FAO Schwarz–themed staycation at the Conrad New York Midtown.

Photo courtesy of Conrad New York Midtown

15. Cozy up with your fave holiday flicks: A Nightmare Before Christmas and Carol at Metrograph; Elf and The Grinch at Alamo Drafthouse; and It’s a Wonderful Life and Eyes Wide Shut at the IFC Center.

16. Set your #ApartmentGoals for 2020 at the Holiday House NYC, a designer show house on the Upper East Side where each room is inspired by the holidays.

17. Exchange gifts with your four-legged bestie (and some cute Insta-famous pups) at the dog-friendly café Boris & Horton.

Photo courtesy of Boris & Horton

18. Get aboard illustrator Richard Scarry’s “Holiday Express” at the New-York Historical Society.

Photo by Don Pollard/Courtesy of New-York Historical Society

19. Start your holiday gift shopping (while also plotting out some festive Instagram posts) at House of Showfields and Industry City.

20. And stock up for your holiday meals at our favorite new grocery store, Wegmans.

21. Salivate your way through Gingerbread Lane, which holds the record as the largest gingerbread village in the worldresiding in Flushing Meadows’s New York Hall of Science…

22. …or build your own gingerbread houses at the James Beard House, Monarch Rooftopand NY Cake

Photo courtesy of NY Cake

23. Make beautiful treats for your annual cookie exchange at The Good Batch and Brooklyn Kitchen

24. …or just pick some up; here are a few of our fave sweets.

25. Find an excuse (or three) to wear your ugliest sweater: Coney Island Brewery, BRIC, and Rosé Mansion are all hosting parties!

Photo courtesy of Rosé Mansion

26. Shop local in unconventional locations: in a Bronx distillery, under the Oculus, at the Queens Museum, and in an 18th-century Dutch Colonial house.

27. Torch and blow your own glass ornaments at UrbanGlass on December 14 and 15.

28. Drive or walk through Dyker Heights, the South Brooklyn neighborhood that single-handedly keeps the holiday lights industry in business by blanketing its homes, lawns, and streets in blinding Christmas decor.

29. If you don’t have the time or energy to travel through the depths of Kings County, the kitschy Pete’s Tavern is fully decked out for the holidays—and has plenty of hot toddies, to boot.

Drink Tipsy History Pete's Tavern NYC
Photo by Sayaka Ueno

30. If your kids are just as obsessed with Christmas lights as you are, Snug Harbor’s Winter Lantern Festival and LuminoCity at Randall’s Island are family-friendly excursions (literally) making the season bright.

31. Party in style and (finally!) have an actually fun New Year’s Eve at the always mysterious McKittrick Hotel, home to Sleep No More.

Photo by Loren Wohl/Courtesy of McKittrick Hotel

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