9 Creative New York City Winter Date Ideas


I feel like I hear so many of my friends complain that there’s nothing to do in New York City during the winter months. Well, I’m here to put the kibosh on that once for and all (with a little help from my boyfriend, Jordan). Dating in the middle of a frigid New York winter isn’t just possible; in my opinion, it’s actually the loveliest, coziest, most romantic time of the year to head out on the town. There are SO many hidden gems (think: candle-lit restaurants, bars with roaring fireplaces, and indoor garden oases …not to mention deals you can only find in the winter.

Below are 6 of Jordan and my personal favorite dates from the past season. Whether you live in the area or you’re just visiting for a weekend, there’s still plenty of time to make ‘em happen with your special whomever. And if you’re not coupled up this year…keep reading, anyway! Go it alone and fall in love with the city all over again. You’ll be glad you did.

Hot Chocolate at Cafe Lalo
Hayden Planetarium

I can’t be the only person in the world above the age of 5 who loves the Planetarium. Just trust me; this place is where it’s at. Especially in the winter! And after you’ve been captivated by the sweet sound of Neil deGrasse Tyson explaining the mysteries of dark matter, you can explore the rest of the National History Museum, or just bounce and go have a hot chocolate at Cafe Lalo (You’ve Got Mail, anyone?!). Or, if you’re not big into reenacting Meg Ryan movies, just grab a bowl of matzah ball soup at famed Jewish deli Barney Greengrass nearby. (Which is notoriously hard to get into on the weekends, but put down your name — it’s worth the 15-20 minute wait.)

There are tons of other great restaurants right there on the Upper West Side if neither of those first options sounds appealing to you — try The Mermaid Inn (I used to love going here), Jacob's Pickles (a little loud, but a fun vibe with great comfort food), Good Enough to Eat (again, huge line on the weekends, but for good reason) are a few favorites from when I used to live uptown. If you want to get a little fancier, try Nice Matin. There’s also a Sarabeth’s up there for standard American brunch fare, or you could run to Irving Farm for a quick coffee. Oh! And Levain, for world-famous cookies.

Bronx Botanical Garden Greenhouse
+ lunch at

Growing up in Connecticut, one of my all-time favorite childhood memories involves the warm, wonderfully humid paradise that is the glass Haupt Conservatory greenhouse at the Bronx Botanical Garden. My dad would bundle up my many siblings and me and drive our giddy, way-too-excited selves to the Garden, where we’d run inside and quickly shed our winter coats. The greenhouse houses the Garden’s rain forest and desert collections, so it legitimately feels like a tropical oasis, and you forget all about the harsh winter air as soon as you step inside.

All these years later, that blast of warm, tropical air still feels like magic, which is why a trip to the Bronx remains one of my favorite winter date activities. You and your person could easily spend an hour or more just wandering around inside the Conservatory; there’s a lot to see and it’s a big space. Just remember to wear layers, because it really will feel like a hot summer day once you’re inside.

Since you’re already up in the Bronx, I’d suggest you pair the Garden date with a trip to the “real Little Italy” around Arthur Avenue and 187th Street. It’s one of New York’s best-kept secrets, in my opinion. Wander through the open-air market, taste pastries and fresh pasta and espresso…or just warm up again with a real-deal Italian lunch at Roberto’s.

magic show at the McKittrick Hotel
+ dinner at
Chop Shop
+ midnight concert at

Okay. THIS. So, I think Jordan would agree that this was possibly the best date night in the history of our date nights…and even just from reading the headline on this one, it’s probably not hard to understand why.

If you’re not familiar with the McKittrick Hotel, it’s this magical, eclectic New York theatre-ish institution that’s home to Sleep No More (which is also apparently a fun date option, but I’ve never been). But they also have other interactive shows, including Wonders at Dusk, which is the show Jordan and I saw back in December (clearly, we went on a lot of fun dates that month!). I honestly don’t think I’d be able to do the show justice by telling you about it here — you just have to go see for yourself.

But what I can tell you is that this was hands-down one of the coolest, most incredible theatrical experiences I’ve ever had. And there’s no rabbit-in-a-hat magic here, by the way; it was completely grown-up (there’s a bar in the theatre with incredible cocktails) and sophisticated, intensely captivating, and a little eerie. But only in the best, most beautiful sense. At times I even found myself in tears (and not just because I’m an emotional freak of NATURE) — it was just sort of an extraordinary experience.

How’s that for a glowing review?

While you’re at the Hotel, you can grab a dinner right there on the roof at Gallow Green, or follow Jordan and my lead and head to Chop Shop just a few blocks away. But if you do step off the McKittrick premises, be sure to head back at midnight to take in the moodiest, most intimate concert at Manderley Bar.

YUP. Midnight. Concert. So very cool.

The end.

Pasta-Making at Aunt Jake’s
+ Drinks at
The Marlton Hotel

Swanky meets cozy meets bar-with-a-fireplace at The Marlton in Greenwich Village. Seriously, it doesn’t get much more romantic than mahogany-lined walls, red leather banquettes, and gloriously dim lighting. SIGH. Jordan and I went here back in December and loved it.

If you want to make an entire night of it, though, head to Aunt Jake’s beforehand. It’s literally just a few doors down on West 8th Street (there are two locations, though, so make sure you’re reserving at the right one!), and they have fabulous, reasonably-priced pasta-making classes almost every Saturday and Sunday. If a full class isn’t your thing, you can also check out Loring Place for dinner — it’s another West Village favorite of mine, and it’s also just two doors down from the coziness over at The Marlton.

Brooklyn Museum
marshmallow-roasting at Olmsted

If there were requisite THINGS to be had / done / eaten on any “coziest winter afternoon ever,” they’d probably include: 1) a museum run, 2) veritable bucketloads of hot chocolate, and 3) ultra-fluffy blankets. Good news: Olmsted in Prospect Park has all three. Well. You’ll have to do the museum run on your own. But once you make that happen, Olmsted is where it’s at. Their make-your-own s’mores — which you roast over coal-fueled fires in their gorgeous backyard while donning BLANKETS and sipping hot CHOCOLATE, for goodness’ sake — feature house-made marshmallows, fancy-as-heck graham crackers from a local bakery, and (thankfully) classic Hershey’s chocolate.Get this: The roasting sticks are even whittled down from fallen tree branches. Which is just about the strangest, coziest, and most delightful thing this gal’s ever heard.

Drinks at the Empire Hotel
+ a night
at the ballet

FUN FACT: Jordan and I met at the Empire Hotel! Actually, we met on a plane months earlier. Accccctually, we met while I was in San Francisco and he was in New York.

It’s complicated.

The point is, we first met face-to-face at the Empire Hotel rooftop. And it was the greatest. So, naturally, that special place had to make this list! It’s also right up by Lincoln Center, which happens to be my all-time favorite, favorite, favorite New York City neighborhood.

If you do follow in our first date footsteps, and you’re not actually on, you know, a first date, you’d be wise to catch a show across the street at Lincoln Center, which is only the greatest cultural institution in the entire world and universe. (I’m partial to the ballet and the musicals over at LCT3, but there are always operas to be seen and symphonies to be heard, too). The events there aren’t cheap (unless you can snag discounted tickets or win them through a lottery), but they’re always beyond worth it and so, so special and memorable. And there’s really no better excuse to dress up.

Dinner in Hell’s Kitchen
+ dancing at
Swing 46 

Before we go any further, ladies and gents, I feel like I should warn you that we’re getting into third-fourth-fifth date territory here. I mean, by all means, go ahead; swing dance your cares away on Date One if that floats your boat. But just know that a dancing date gives the dangerous impression that you’re completely, rapturously, head-over-heels in love.

At least, that’s the vibe Jordan and I were giving each other when he took me here last year.

But if you’re cool with that — and willing to pull out all the stops — then you GO, reader. You go.

So, about Swing 46. It’s not somewhere I’d be thrilled to actually wine and dine the entire night away, per se. It’s more of a slapdash, late-night, after-the-real-date kind of affair. But assuming you grab dinner in the neighborhood first (which shouldn’t be too difficult, since Hell’s Kitchen boasts upwards of, what, 83 katrillion restaurants?) — and assuming you understand the aforementioned risks associated with a dancing date — you’re guaranteed to have the best night ever here.

And no, you don’t have to actually know how to dance. There’s live music and happy people and I promise you’ll be smiling and laughing and twirling right along with them before you know it.

Angelika film Center
+ Drinks at
Pegu Club

Love Pegu Club! It’s a trendy, dimly-lit spot way downtown with spacious booth seating and excellent drinks. (Random note of caution — I did once forget to bring an ID and wasn’t allowed in. At age 24, mind you. So, don’t do what I did.)

Before you grab a drink, head to Angelika, which is an adorable theatre showing (mainly) indie films. Jordan and I do not agree on movies (I usually only go for the ones with a romantic plot and equally romantic sub-plot and very little other-type-of- plot) but there’s something for everyone here. Promise.

Skating at Rockefeller Center
dinner at Le Colonial

Skating, duh! There’s not much to say about this one, except that it’s a classic — the obvious wintertime date. And though you’re inching closer to Times Square and smack-dab in the heart of midtown, Rockefeller Center is just as magical as you think it’ll be. (If skating’s not your thing, I actually also love throwing on some extra layers and going up to the roof of 30 Rock (though you’ll have to purchase a ticket and plan this ahead of time) — you get an incredible, picture-perfect view of the Empire State Building. Even after nearly a decade of living in New York City and a few years working in the building at my former job, that rooftop view still takes my breath away.

Either way, Le Colonial is your best bet for a classy midtown joint that you’ll come back to over and over again. It’s one of Jordan and my all-time favorite NYC date spots and is such a hidden gem. The bar itself is tucked away on the second floor of the establishment, so it all just feels very romantic and secretive. We’ve only had drinks there, but they do serve a full menu of upscale French-Vietnamese food, and the restaurant decor is supposed to be reminiscent of 1920s Southeast Asia.

That’s all I’ve got! Have you guys tried any of these spots (or do you have others to share)? Which ones do you love most?