There is something about New York City at Christmas that keeps me coming back.

Maybe it’s the lights strung above the streets, the shop windows dressed for the season, or the way the city seems to lean completely into the magic of December. But for me, I think part of it will always be nostalgia.

When I was younger, my mom and I used to take an annual mother-daughter trip to New York with a local church. We would walk through Little Italy and Chinatown, visit the American Girl store, see the Rockefeller Center Christmas tree, and experience the city at its most magical time of year.

Years later, coming back at Christmastime still brings some of that wonder with it.

For this trip, my friends and I arrived on a Friday morning and left Sunday afternoon. We had a handful of reservations, but some of my favorite moments came from the things we hadn’t planned at all: racing through Manhattan on Citi Bikes, splitting bagels while waiting outside Rolf’s, stumbling upon Christmas music at dinner, and waking up Sunday morning to find the entire city covered in snow.

If you’re dreaming of your own Christmas weekend in New York City, here is how we spent three wonderfully festive days in the city.

Friday: The West Village, Little Italy & Late-Night Jazz

We left Virginia early Friday morning and arrived at Moynihan Train Hall, dropped our bags at our friend’s West Village apartment, and almost immediately headed back out.

First stop: Boucherie.

We had walked past Boucherie on several trips before and always wanted to go inside. Around Christmas especially, the restaurant is beautifully decorated and always seemed to be bustling, so this time we knew better and made a reservation. This photo above was from the year prior. We stopped outside to get a picture and knew we had to make it inside next year! We did it!

It was the perfect cozy lunch after a morning of traveling–hearty, warm, and delicious drinks!

Naturally, I couldn’t turn down the French onion soup—warm, cheesy, and classic—and an espresso martini provided exactly the little pick-me-up we needed after our early morning.

After lunch, we took a slow walk through the West Village to let our food digest and enjoy the neighborhood at Christmastime.

We love just strolling through the West Village when we are there. Brownstones, little restaurants, decorated stoops, people coming and going—and also some nostalgia from previous trips and it being where our friend lived and we visited for so many years!

A Coffee Stop at Fellini

Gabrielle and I are the coffee connoisseurs of the group, so another caffeine stop was inevitable.

We stopped at Fellini Coffee, one of our favorite little West Village coffee spots, for another pick-me-up before what we knew would be a late night.

Then we headed back to our friend’s apartment to finally see her after work, catch up, and get ready for a fun evening ahead seeing the Rockefeller Center Christmas Tree, dinner plans in Little Italy, and a jazz show! 

Seeing the Rockefeller Center Christmas Tree 🎄

Before heading home to get ready for dinner, we made our way uptown for one Christmas tradition that has become especially meaningful to us: seeing the Rockefeller Center Christmas Tree.

Caitlin’s roommate works at Rockefeller Center, and for the past two years she has taken us to see the tree up close. It has quickly become one of my favorite traditions of our annual Christmas weekend.

If you’ve ever visited Rockefeller Center in December, you know just how crowded it can be. It seems as though there is never really a quiet hour, with people gathered several rows deep trying to catch a glimpse of the tree. So having the chance to step away from the crowds and stand so close to it feels incredibly special.

And no matter how many times I’ve seen it in photographs or Christmas movies, the tree really is breathtaking in person. The sheer size of it, the thousands of lights, the skating rink below, and Rockefeller Center glowing all around you—it’s one of those New York Christmas traditions that deserves the hype.

There is also something really sweet about knowing that this has now become our little tradition. Two Christmases in a row, the same friends, the same tree, another year of memories.

Dinner in Little Italy

That evening, we had dinner reservations at Da Gennaro in Little Italy, a historic neighborhood in Lower Manhatten centered around Mulberry Street.

I always love walking through Little Italy when I’m in New York because it immediately takes me back to those childhood trips with my mom. We’d walk through Little Italy and Chinatown, visit the American Girl store, see the Christmas tree—it is probably one of the reasons New York at Christmas still feels so nostalgic to me.

And that night, we got one of those completely unexpected New York moments.

While we were seated at dinner, a band of musicians came strolling through the restaurant playing Christmas classics. They took requests from the crowd, everyone began singing along, and suddenly the entire restaurant seemed to be part of it. It was the best surprise and had all of us smiling, swaying, and singing along to their classic Christmas carols! It was amazing and so much fun!!

If you’re looking for a sweet treat after dinner, stop at Ferrara Bakery & Café. Located at 195 Grand Street, this bakery has been serving Italian pastries since 1892 and I can confirm it is delicious! We would always make sure to hit this stop growing up on our trips to NYC!

Jazz at Mezzrow

Warm from dinner—and perhaps from all the singing—we bundled back up and headed into the cold for Mezzrow Jazz Club, where another wonderful college friend who happened to be visiting New York with her husband met us.

We settled in for live jazz, drinks, and a cozy evening together with friends. We saw the Adam Birnbaum Trio at 10:30 p.m. which was late, but you have to stay out late in the city that never sleeps, especially on your first night to kick off a great trip!

Afterward, we found a local dive bar and caught the end of the Golden State Warriors game.

And with that, we decided this was the perfect cap to end our first night in New York City at Christmas.

Saturday: Rolf’s, Christmas Markets & Cocktails at The Plaza

Saturday morning was my favorite part of the entire trip.

And almost none of it was planned.

We had purposely left most of Saturday open, with just one reservation on the calendar: drinks at The Plaza that evening.

After sleeping in following Friday’s travel and late night, I brought up something I’d been talking about forever.

Rolf’s.

I had wanted to see Rolf’s German Restaurant at Christmas for years. Not necessarily because I was desperate to have a full meal there, but because of the decorations.

And, of course, bonus points for being German.

Rolf’s is famous for its completely over-the-top Christmas décor. The restaurant says its decorations take approximately three months of work and include more than 200,000 lights alongside thousands of ornaments and icicles, vintage pieces, dolls, wreaths, garlands and ribbons.

Getting a last-minute dining reservation during Christmas season seemed nearly impossible. But then we had an idea! What if we just got there right when they opened and tried to get into the bar?

And thus began one of my favorite New York mornings ever.

Our Rolf’s Christmas Mission

Caitlin and I quickly got ready while the other girls went to grab bagels and planned to meet us there.

Then Caitlin and I hopped on Citi Bikes.

Electric Citi Bikes.

In Manhattan.

I had never ridden an electric bike before, much less through one of the busiest cities in America. I did run into the back of Caitlin once, but we arrived at Rolf’s—with ourselves and the bicycles intact.

Success.

There was already a line wrapping around the corner, but it looked promising.

We immediately called the girls: We have a spot. No rush. While we waited, we started chatting with the people around us. One couple told us they do this every year—get in line early and start their Christmas day at Rolf’s with drinks.

Eventually, the rest of our group arrived carrying bagels, which we split among ourselves while standing in line. A very practical decision considering what we were about to do before noon.

The line slowly crept forward.

We huddled together against the cold.

And then we were in.

Christmas Exploded—in the Best Possible Way

Nothing quite prepares you for the inside of Rolf’s.

A long bar stretches through the restaurant, but it’s almost difficult to notice anything at eye level because your eyes immediately go upward.

The ceiling isn’t simply covered in decorations.

It’s swathed in them.

Red and gold ornaments cascade overhead alongside angels, garlands, lights, ribbons, greenery, and what seems like every Christmas decoration imaginable. Nearly every available inch has been transformed.

It felt as though the Ghost of Christmas Past himself had decorated the place.

It was a amazing and we loved every bit of it! We couldn’t stop snapping photos. If the decorations weren’t already impressive enough, the drinks took us over the edge.

The holiday cocktail menu was just as fun, and while we were there we met a family whose story made the morning even better. The menu varied from all sorts of festive cocktails from warm mulled wine to spiked a spiked almond egg nog–my favorite!

Every year, two families reunite for an annual bar crawl. Nieces, nephews, cousins, and relatives who now live elsewhere come back to New York on the same weekend, and Rolf’s is where they meet to begin the day.

We laughed, talked, drank our Christmas cocktails, and all looked at each other thinking the same thing: We need a tradition like this!

For something we’d barely planned that morning, Rolf’s became my favorite memory of the entire weekend.

And here’s a useful tip if you want to recreate it: Rolf’s currently confirms that its bar is first come, first served, while reservations are for dining.

Union Square Holiday Market

From Rolf’s, we wandered toward the Union Square Holiday Market.

We found a photo booth and, obviously, squeezed inside for pictures. We browsed the little wooden stalls, found a few pretty rings, and essentially created our own mini walking food tour.

Instead of committing to one lunch, we tried different things as we went—creamy Alfredo from one stand, empanadas from another, and whatever else looked good enough to share.

That is one of my favorite ways to do a Christmas market: don’t arrive with a plan. Walk around, split things, and try whatever catches your eye.

Eventually, we subwayed back to the West Village to rest our feet before the evening.

Pizza, Wine & Getting Ready

Before heading home, we stopped at our favorite neighborhood wine shop for a bottle and grabbed squares from our favorite pizza place.

Back at the apartment, we kicked up our feet, ate my favorite Made in New York pizza, drank wine, and slowly got ready for the reservation I had been looking forward to all weekend.

The Plaza.

Christmas Cocktails at The Plaza

I’ve always wanted to experience The Plaza at Christmastime.

It is one of New York’s most iconic hotels, but for me, Christmas adds another layer of nostalgia because of Home Alone 2. The Plaza is so woven into that movie—and into this almost storybook version of Christmas in New York—that walking inside during December felt special in a way I can’t quite explain.

The Christmas trees, ribbons, lights, and decorations made the already grand hotel feel even more magical.

One day, I would love to actually stay there.

For now, drinks at The Plaza felt pretty wonderful.

Our friend Brooke had made our reservation well in advance because she knew this was something we wanted to do. That’s something I would absolutely recommend if you’re planning your own Christmas trip: don’t leave The Plaza until the last minute.

The Palm Court currently accepts evening reservations and, for its holiday experiences, The Plaza releases reservations to the general public 60 days in advance.

We all ordered festive cocktails, but I think mine won.

The Peppermint Twist arrived bright green with a candy cane hanging from the martini glass. I immediately renamed it The Grinch because of how green it was! It was honestly so green, it was hilarious.

We were able to wander through parts of the hotel before and after our reservation, admire the decorations, and take plenty of pictures to remember the night.

It was elegant, festive, slightly ridiculous thanks to my green mouth—and exactly the kind of Christmas-in-New-York experience I’d hoped it would be.

One More Stop: The Dead Rabbit

Because apparently we weren’t finished yet, we took the subway downtown to meet more friends at The Dead Rabbit NYC in the Financial District.

And as we made our way across the city…

it started to snow.

The Dead Rabbit is on Water Street in Lower Manhattan, so your Financial District memory was right.

We ended Saturday night with friends, drinks, and snow beginning to fall outside.

We couldn’t have planned a better ending if we’d tried.

Sunday: Waking Up to Snow in New York

Sunday morning, we woke up and looked outside.

New York was white.

The streets, sidewalks, cars, rooftops—everything had been covered overnight in fresh snow.

After a weekend filled with Christmas decorations, markets, holiday cocktails, music, and old traditions, somehow New York had saved its best trick for last.

We bundled up and braved the cold for Sunday church at Church of the City.

It was Advent, which made worship that morning feel especially meaningful after such a festive weekend.

After church, we crossed over toward Central Park and caught a glimpse of the park blanketed in fresh, powdery snow.

It was quiet and beautiful and felt almost impossibly perfect.

And then, just like that, we were back where we’d started.

Moynihan Train Hall.

Bags in hand.

Ready for the train home.

All in All

You really don’t need an entire week in New York to experience Christmas magic.

Sometimes, a weekend is enough.

We ate French onion soup and Italian food. We listened to live jazz and Christmas music. We raced through Manhattan on Citi Bikes. We split bagels while waiting in the cold. We drank Christmas cocktails beneath what felt like a million ornaments at Rolf’s and dressed up for drinks at The Plaza.

We saw old friends, made new ones, revisited childhood memories, and stumbled into moments we never could have planned.

And then New York gave us snow.

Maybe that’s why I continue coming back to this city at Christmastime. It isn’t only the decorations or the markets or the famous tree.

For me, it’s the memories attached to all of it. The ones I made here as a little girl with my mom. And the new ones I’m making now with my friends.

This New York Christmas weekend is one I’ll remember for a very long time, and I’m so glad I get to share a little piece of it with you.

If you visit any of these places—or have a favorite New York Christmas tradition of your own—I would love to hear about it.

Merry Christmas and happy holidays!!

Thank you for reading <3

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