A Very New York Holiday Season

Its the Most Wonderful Time of Year in New York

The bright lights, big city feel hits extremes this time of year when New York City gets dressed up for the holidays.  The city itself has enough to see, eat, and do to keep you busy for years, but adding that touch of holiday sparkle can make it even more daunting.  Here is my guide to what not to miss during New York’s holiday season!

What to see:

Dyker Heights, Brooklyn – This neighborhood of Brooklyn decorates so brightly I’m sure you could pinpoint it from outer space! There are guided tours that require booking in advance to see the lights, or you can walk it yourself.  Its best to wait until mid December to check them out so the lights will be in full swing.

Rockefeller Center Tree – Its a classic.  While the crowds can be ridiculous I think seeing the tree is such a spectacular sight.  I’ve gone to see the tree every year for the past 27 years and I recommend it to everyone.  Ice skating below the tree is also a real treat but the lines can be dreadful.  If you are an early bird I say go for it, otherwise, keep reading for other rinks to hit.

Department Store Windows – Oh the windows.  Its actually insane to hear how much production and money goes into these windows every year.  I had a roommate who worked at Lord & Taylor and told me the cost just for the unveiling party, which I’ll keep a secret but say it is more than I’ll see in a lifetime (fingers crossed that changes though).  Try to visit the tree at Rock Center after dusk so you can see the light show on Saks Fifth Avenue.  I love watching it from across the street in the row of angels.  Inside is also a real site through the bottom floor.  Its done up in beautiful white decorations. Another favorite of mine are the Tiffany windows, because who doesn’t love diamonds posed in a wintry setting. Bergdorf Goodman’s windows are an ode to New York this year, so make sure you check those out!

Where to eat / drink:

Rolfs – This is a must visit place when in New York for the holidays.  Rolfs is a German restaurant open year round, but come holiday time it looks like Christmas exploded inside the bar.  There are more decorations than in the North Pole.   The line will normally wrap around the corner, but it tends to go by quickly because it does get quite warm inside.  I’ve only been for drinks, and lucky for you I’ve tried them all. The spiked warm apple cider and burnt toasted almond are my 2 favorites but they are all good, just depends on your taste preferences.

230 Fifth – I love this rooftop year round but there is just something about sitting in an igloo on the top of a building in Manhattan that screams fun. I’ve been for light bites and drinks here, and while the prices are a little nuts, I’ve not been disappointed.  Its a great spot year round as well, and has incredible views of the city.

Baita – This is the rooftop at Eataly, which turns into an Italian Alps chalet in the winter.  Anything Eataly is a must, its just the most wonderful place in the world but the rooftop is very cool.  They’ve got a great selection of beer, wines and cocktails, including some high altitude wines which are delicious.  It’s also home to New York’s first Polenta Bar, because, who doesn’t love polenta?

Shake Shack Madison Square Park – If you haven’t eaten Shake Shack, you must, and if you have, then you know you must.  There are a ton around the city but I say go to Madison Square Park for a few reasons.  For starters, its the original location for the brand, but I also like the decorations put up in the park.  On December 7 the gingerbread houses will go up for a 2 week stay.  So you can enjoy a gingerbread milkshake in the gingerbread house!

What to do:

Ice Skating – So many places around the city put out a skating rink for the holidays, that you have every opportunity to avoid Rockefeller Center.  Its an experience, I’ll give it that, but overpriced and overcrowded.  I would suggest ice skating at Wollman Rink in Central Park, Bryant Park Winter Village, or at the Standard Highline for a change of scenery.

Holiday Markets – The Winter Village at Bryant Park is by far my favorite place to go during the holiday season.   Each year there are a ton of pop up shops and food options alongside the skating rink and main restaurant.  I love 5th&Madison candles, I stock up on Molokai when I’m there!  This year there is also a Dö outpost and Insta-famous, Chick’n Cone.  Don’t miss Arancini Bros. and their French Onion ball though, its unreal! Union Square and Grand Central holiday markets also have great shops and dining.  Union Square has a Milk Bar outpost so you can stock up on compost cookies and birthday cake truffles!

Radio City Rockettes – If you’ve never seen the Christmas Spectacular, you are missing out.  I’ve seen it multiple times, and honestly if you don’t splurge for the first 2 tiers I don’t think you are going to really get the beauty of it. Underneath Radio City there is a food hall so if you are looking to grab a quick bite I say get Harry’s Italian Pizza Bar, its delicious.

Santa Con – Going to be in town December 9? Prepare to see thousands of Santas running around NYC, and no, their bags are probably not filled with presents. If you see a bar overthrown in red and white and are not in a party mood I suggest finding a new location, however, they are a really fun bunch to throw a few drinks back with.

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