A Winter Wonderland in New York City

Let The Big Apple’s cozy vibes warm you during the chilliest season

photo courtesy of Erin Kestenbaum

New York City in wintertime – what a cinematic dream, right? Holiday markets, jazz music, flea markets, ice skating and even a hot chocolate festival are all just waiting to be your snowy-season utopia.

Dine Like Alpians

A heated rooftop restaurant and microbrewery, La Birreria, has the comfort of a snug mountain lodge with city convenience – the name’s concept actually translates to “small ski lodge in the Alps.” Adirondack chairs, pine trees and vintage Dolomite artwork decorate the eatery, featuring meats and cheeses, warm hearths, craft beer, more than 60 Italian wines, along with winter warmer staples like hot cocktails, tea, hot chocolate, espresso and eggnog.

The retractable roof and heaters keep the place open during all weather, too, be it rain, shine or snow. On the 14th floor at Eataly Italian marketplace headquarters at 200 Fifth Ave., La Birreria is open Mon. to Thurs. and Sun. 11:30 a.m. to 11 p.m.; Fri. to Sat., 11:30 a.m. to midnight (eataly.com).

Visit the Outdoor Market

Brave the cold for Union Square Holiday Market, if nothing else. This European-style winter market boasts more than 150 local and national vendors offering handcrafted gifts, ranging from jewelry and accessories to leather goods and artwork. The market is open through Dec. 24 (urbanspacenyc.com).

Stroll Past Cheery Storefronts

Navigating the city’s busy streets can be stressful at any time of the year, but luckily around the holidays passersby can at least feast their eyes on department stores' festive display windows – particularly on Fifth Avenue. From Bergdorf Goodman to Bloomingdale’s, Henri Bendel to Lord & Taylor and Macy’s, let your eye be the judge of the best.

Grab a Pair of Ice Skates

Of course, visitors have to lace up and go ice skating at one of the city’s seasonal rinks at least once. There are plenty of options in Bryant Park, Van Cortland Park, Central Park, and others around the city. Tip: go to the outer boroughs (Brooklyn, the Bronx, Staten Island, or Queens) for the less-crowded rinks.

Warm Up With a Jazz Festival

From Jan. 5-10, Winter Jazzfest gathers leading musicians from around the world, offering shelter from the cold at snug downtown venues. Ten locations and more than 100 artists are participating in the festival, scattered throughout Greenwich Village (winterjazzfest.com).

Search for Local One-of-a-Kinds at Brooklyn Flea

Brooklyn Flea, a market hailed by travel magazines as one of the best in the world, features furniture, vintage clothing, collectibles and antiques. Plus delicious fresh food. Open every Saturday and Sunday, the market has moved indoors at Skylight One Hanson in Williamsburg, from 10 a.m. to 6 p.m., for the winter months (brooklynflea.com).

Go Sledding!

Once the snow arrives, hit the hills in the city's boroughs, from Crotona Park in the Bronx to Fort Greene Park in Brooklyn. Central Park’s most popular spot, Pilgrim Hill (enter at 72nd Street and Fifth Avenue), is popular for its steepness and family-friendly vibe. Another option is Uptown’s Inwood Hill Park, which attracts crowds to its moderate slopes and picturesque views of the Hudson River. Sled like a Brooklynite by going to Prospect Park’s Long Meadow — perfect for all ages — with the added bonus of free hot chocolate at the nearby Picnic House.

Escape the Cold at Art Museums

Warm up while gazing at the work of Picasso, Monet or Pollack this winter. Start at The Metropolitan Museum of Art, one of the city's largest and most-visited attractions, where an entire day spent wandering its majestic halls only begins to scratch the surface of the museum’s collection (metmuseum.org).

Indulge at a Hot Chocolate Festival

Masterminds behind City Bakery, a Manhattan mainstay frequented for its gourmet coffee and pretzel croissants, devote the entire month of February to their hot chocolate, one of the city’s most celebrated winter-warming beverages. Each day of the 26th Annual City Bakery Hot Chocolate Festival touts a new flavor of steamy hot bliss, ranging from Vietnamese cinnamon to a Moulin Rouge flavor, which sounds bizarrely promising (thecitybakery.com).

Have a Pint & a Chat at Fireplace Bars

Shoolbred's is an authentic Scottish pub in the East Village, with a happy hour featuring two-for-one drinks daily until 8 p.m. Need we say more? Oh, and it has a fireplace. Other cuddle-up fireplace bars include Brandy Library, Black Mountain Wine House, and Fawkner.