Holiday Planning: 5 Festively Free Activities in NYC


For many of us, this time of year is a logistical nightmare, as lining up flights home, planning vacation time, and everything in between can be a test of patience of biblical proportions. For those of us staying put however, it can often mean playing host to friends and family from out of town, which can be just as diabolical.

This year more than ever, the perfect host will be one who pays attention to the bottom line. For the sake of your own hip pocket, or in homage to the holiday spirit itself, keep this guide handy. Below are StyleCaster’s favorite holiday activities, all festively free this winter.

Chess in Central Park:

For most of us, the proposition of a game of chess in central park would call for a picnic and SPF with many New Yorkers pegging this as a summertime-only activity. However, for those of you with an encyclopedic knowledge of Central Park, you’ll perhaps be familiar with the Chess and Checkers House, set back from the 65th street entrance, or a couple of hundred yards north of the Trump ice skating rink. The Chess and Checkers House was a genius gift from the philanthropist Bernard Baruch, and has stood atop the “Kinderberg” rock cropping since 1952.

Worth the visit alone for the fantastic views of midtown Manhattan, the deal is made even sweeter by a team of volunteers that staff the Chess and Checkers House year round, ensuring that there are enough tables and chess sets for everyone–free of charge. Just make sure you bring your photo I.D. and you’re all set.

The Chess and Checkers House is open Tuesday through Sunday, 10 am to 4 pm.


Ice Skating at Bryant Park:

Sometimes it’s the most obvious things that New Yorkers put off or never get around to doing. It’s not uncommon to meet a native who’s never been to the Statue of Liberty, Central Park Zoo, or The Empire State Building. While most of us could probably find 100 better things to do with our time than wait in line for the metal detector at a national monument, ice skating is still one winter activity that doesn’t require photo ID and a federal police background check.

While the rink at Rockefeller Center might be the most well-known, it is also the most crowded and most expensive. The same goes for the Trump-owned Central Park location, which is a little bit like skating in the nosebleed section of a Miley Cyrus concert these days.

Strangely, what might be the city’s most well situated ice skating rink at Bryant Park is also the most overlooked. Without the madness you’ll find at other Manhattan rinks, you’ll also be able to skate all day for free! Catering to a crowed that is a little more local.

The rink is open Sunday to Thursday until 10 pm, and on Friday and Saturday you will be able to skate up until the clock strikes midnight.


Art Openings:

One of the most frustrating things about New York City is how early in the day the major museums and art galleries close. With the exception of a few late nights scattered throughout the year, most galleries are done for the day at around 5:30 pm, which forces you to often sacrifice a day on the town to make sure you fit some art into the itinerary.

Although this is often the sacrifice you have to make in order to see the major collections at the MoMA, the Met and the New Museum, there is still a smorgasbord of art to be seen after dark as New York City’s independent galleries and museums come to life. With a handful of openings and parties scheduled on almost every night of the week, independent and commercial galleries can be the perfect place to take friends and family after a long day’s shopping trip or as a pit stop before a late dinner.

Once upon a time, the art world was largely closed, allowing access only to those “in the know.” With sites such as it is easier than ever to plan which openings you’ll attend though their online calendars and message boards. With parties all year round open to the public in the vast majority of cases, you’ll be hard pressed to find a better way to end the day with an open bar.

Need help balancing your work life with holiday planning? See our helpful tips.


Sledding in Queens:

Subject to an especially heavy dumping of snow, Lower Highland Park (Jamaica Ave & Elton St, Queens) hosts its annual snow day sleigh-riding fest, open to anyone who enjoys sledding, live music, and hot chocolate–all of which are provided for free. Although it’s nearly impossible to plan in advance for this once a year winter festival, when all your other plans are cancelled in the event of such a snowstorm, this could be a terrific stand by.

Lower Highland Park is also accessible from Brooklyn’s J subway line. Be sure to check for updates on New York’s parks website before heading out to Queens. Alternatively you can call the park for more information at 718.235.0815.


Brooklyn Heights Promenade:

There might not be a better view of Manhattan than that from the Brooklyn Heights promenade. Stretching 1/3 of a mile perched high above the Brooklyn Queens Expressway, the promenade offers an unobstructed view of lower Manhattan all the way up to midtown and beyond. In winter, the viewpoint is far less windy than its lofty counterparts at the Empire State Building and Rockefeller Plaza and can be reached via a short walk across the Brooklyn Bridge or via the 2/3 subway line.

As well as the perfect winter view of Manhattan and the Statue of Liberty, the promenade is located within the Brooklyn Heights historic district, one of the most intact 19th century urban landscapes in North America. Home to famous writers such as Truman Capote and Arthur Miller, Brooklyn Heights was immortalized in the Bob Dylan song “Tangled Up Blues,” written about his time living on Montague Street.

Take a look at the perfect holiday outfit for strolling along the promenade.