The Coolest Things to Do in NYC This Winter Season

The days might be short but you can still make new memories.

Ice Rink at The Seaport
Ice Rink at The Seaport | Photo by Jane Kratochvil
Ice Rink at The Seaport | Photo by Jane Kratochvil

Winter is a bustling season in New York City with numerous holidays and annual traditions that help the cold days go by a little quicker. Even after the new year, magic fills the city. Sure, you won’t be picnicking at the park for the next few months, but you can certainly make new memories.

This year, there's plenty to be excited for as covered patios and holiday pop-ups return, along with can’t-beat entertainment in the form of musicals, museums, and leisure activities. Here are our top recommendations for how to pass the time with ease between now and March.

Union Square Holiday Market
Union Square Holiday Market | Photo by Jacob Williamson

Shop local markets for holiday gifts

Through December
Various locations
There’s no better feeling than finding a unique gift (even if that gift is for yourself) from a local artist or entrepreneur. The NYC holiday markets, posted up in various hotspots around town through December—Union Square, Bryant Park, Columbus Circle among them—offer a variety of artisan crafts, home decor, and wearables, plus delicious treats to keep you satiated while you browse. It’s a quintessential holiday season experience, whether you purchase something or not, and certainly worth venturing out for on a slow winter day.
Cost: Looking is free

Naughty or Nice
Photo courtesy of Naughty or Nice

Various dates
Various locations
Some venues know how to transform for the Christmas season with December makeovers that get guests in the holiday spirit: Try the The Dead Rabbit’s Jingle Jangle pop-up in FiDi and Loreley Beer Garden’s Heated Winter Wonderland in the Lower East Side. Others stay festive all through the cold months, like the ski-resort-themed Haven Ski Chalet in Midtown and The Hideout at Gallow Green in Chelsea, both on rooftops. Whether it’s snowing outside or not, New York’s winter pop-up bars will have you eager to cozy up with a hot toddy.
Cost: Varies

Sunday, January 1
Coney Island
For the 120th year, the bravest among us will gather at Coney Island to start their year with a refreshing shock to the system: the Polar Bear Plunge. The annual event, in which thousands crowd on the shore wearing everything from bathing suits to costumes, is exactly as it sounds: You run full speed into the ocean, freeze your tail off, and feel invigorated to make the new year a great one. It’s simple, and it supports a good cause: Donations from the event support Coney Island organizations, giving them a boost of funding during the off-season that helps keep the community afloat.
Cost: Free, but donations are encouraged

Eastwind Oliverea Valley
Eastwind Oliverea Valley | Photo by Lawrence Braun

Starting Friday, January 6
Big Indian, New York
The Catskills are a beautiful getaway year-round. Though camping in the mountains might be better fit for the summer, Eastwind Hotels found a way to bring the beauty of the region to New Yorkers, even in the winter. Eastwind Oliverea Valley is an unconventional, Scandinavian-inspired hotel built into a mountainside, with only 30 rooms to preserve its tranquility—each offering a unique cabin-like experience. The property includes an outdoor pool, sauna, communal fire pit, hammocks, and a full bar-restaurant. Who said winter has to be spent inside?
Cost: Varies, but expect to pay a little extra for the experience

Thursday, January 12 to Wednesday, January 18
Various locations
Over the course of one week, more than 100 groups—400-plus musicians—will perform across 15 venues for the NYC Winter JazzFest, a celebration of all things jazz that also features some talks sprinkled throughout. If you aren’t into jazz, you’ve clearly never seen La La Land or Soul, which remind everyone that it’s never too late to get into the genre. Try something new and purchase a ticket. Right now, two-day passes, single-day Manhattan passes, and single-day Brooklyn passes are all on offer.
Cost: Single-day passes start at $65; two-day passes start at $105

Tuesday, January 17 to Sunday, February 12
Various locations
New York City Restaurant Week is the time of year that locals can eat their way through the city without spending thousands of dollars. For nearly a month, hundreds of participating restaurants across NYC will offer prix-fixe meals to guests for a discounted price, making the high-life more accessible to the other 99%. Starting on Wednesday, January 4, interested parties can visit the event website and begin making reservations—just be sure to review each individual restaurant’s options and dates of operation so there aren’t any surprises when you show up.
Cost: Diners will pay either $30, $45, or $60, depending on the meal option they select

Aunts et Uncles
Aunts et Uncles | Photo by Cole Saladino for Thrillist

Support Black artists, chefs, and entrepreneurs during Black History Month

During February (and beyond!)
Various locations
The month of February is an annual reminder of the role that the Black community has played in America’s history, actively plays in America’s culture, and will play in America’s future. In honor of Black History Month, you can make an intentional effort to support Black-owned businesses, whether that's dining out, shopping locally, or ordering from online shops. It's also a great time to educate yourself by visiting a variety of historic sites across the five boroughs, and watching both impactful and entertaining films by Black directors.
Cost: Varies

Find your plus-one before wedding season returns

During February (or whenever, really)
Various locations
Being single is hard when you’re surrounded by couples, but Valentine’s Day doesn’t have to be lonely. Whether you’re looking for a forever love or a brief encounter, destiny sits in your hands during the upcoming season of romance. In the spirit of Valentine’s, consider stopping into one of several speed dating events hosted at bars around the city this February—including one for everyone, one for ages 30-45, and one specifically for Black men and women. If the idea of speed dating feels too forced, linger at one of the city’s best bars for singles. And if all of this feels too heteronormative, take comfort knowing that sparking conversation is even more welcomed at queer-centric bars (of which NYC has plenty!).

Pebble Bar
Pebble Bar | Photo by Cole Saladino for Thrillist

All season long
Midtown
Rockefeller Center is the uncontested heart of all things winter, but tucked beneath its outdoor ice rink and Christmas tree is a remodeled plaza of shops and eateries to explore. The center is now filled with top-tier bars, so you can catch up with friends in a convenient location, and modern restaurants helmed by culinary champions, so you can kick your feet up after a day of roaming Midtown. Of course, it has all the sweets, too: Magnolia Bakery, Breads Bakery, Dough Doughnuts and the recognizable FAO Schwarz candy shop. If you’d sworn off the old Rockefeller Center in your past life, give the new one a chance.
Cost: Varies

Whenever it snows
Various locations
You might equate sledding with the mountains, but the city has plenty of hills fit for a ride any time snow falls. In Central Park, there’s the ever-popular Pilgrim Hill and Cedar Hill. In hilly Upper Manhattan, just about any park will suffice. Governors Island is a fun day-trip destination, the major Brooklyn and Queens parks are well-suited, and Clove Lakes Park in Staten Island works just great. The city’s your playground, so play on it!
Cost: Free

All season long
Various locations
Bar trivia is a staple of any town’s nightlife scene and New York is no exception. NYC Trivia League is a free, citywide organization that organizes trivia events and allows teams to compete any night of the week they choose, at one of dozens of participating bars and restaurants. Each week your team’s points will be tallied, and at the end of the “season,” the top teams in the city will face off in a championship dubbed the King’s Cup. You can jump into a season at any time—just check the calendar to find the venue and time that works best for you.
Cost: Free, and prizes are awarded to winning teams

Winter Village at Bryant Park
Winter Village at Bryant Park | Photo by Angelito Jusay for Bank of America

All season long
Various locations
New York has some of the most recognizable ice skating rinks in the world, like the Rockefeller Center rink beside the city’s world-famous Christmas tree and the Wollman Rink in the heart of Central Park. But that’s just the beginning: At least a dozen impressive venues welcome skaters around the city, with some staying open until the first signs of spring—just be sure to check the rink’s season-end dates before heading over. Whether you’re bringing a love interest, going solo, or giving the kids a day to remember, ice skating is one of the best ways to shine a bright light on a cold winter day.
Cost: Varies

'A Strange Loop'
'A Strange Loop' | Photo by Marc J. Franklin

All season long
Theater District
Broadway in December offers a mix of plays and musicals and classics and originals, and the hottest show in town is constantly changing as new productions open and casts rotate. Right now, all eyes are on the brand-new and verifiably adorable musical Kimberly Akimbo, Lea Michele’s portrayal of Fanny Brice in Funny Girl, and best new musical winner A Strange Loop, which closes on January 15. No matter your interests, you’ll find something to adore on Broadway’s extensive winter roster.
Cost: Varies

"Gustav Klimt: Gold in Motion" at Hall des Lumières
"Gustav Klimt: Gold in Motion" at Hall des Lumières | Photo courtesy of Hall des Lumières

All season long
Various locations
There’s a reason tourists flock to museums when they visit New York—they’re home to art, artifacts, and experiences found nowhere else in the world. Right now, you can learn about queer liberation at MoMA PS1, ageism in relation to sexuality at the Museum of Sex, and the power of shoes at The Museum of FIT (and those are just starting points).
Cost: Varies, but some are free!

Veselka
Veselka | Photo by Cole Saladino for Thrillist

All season long
Various locations
New York’s food scene is so eclectic that it’d be a sin to rely on chain restaurants when you’re in the five boroughs. With the best pizza and bagels in the world, multiple Chinatowns, two Little Italys, and just about every cuisine imaginable represented, there are endless must-try dishes that’ll take you all winter to get through—like cheesecake from Junior’s, a hot dog from Gray’s Papaya, dim sum from Nom Wah, pancakes from Clinton Street, and a chopped cheese from Hajji’s. Don’t feel overwhelmed, we’ll walk you through it.
Cost: Varies

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Kyler Alvord is a former staff writer at Thrillist who keeps coming back for more. Find him on Twitter and Instagram, or in any Brooklyn coffee shop that serves bagels.