A Cozy, Can’t-Miss Winter Weekend in New York City
Yes, it’s chilly—but winter is hands down my favorite
time for Connecticut residents (newcomers and long-timers alike) to make New
York City a weekend getaway. January through early March is the city’s sweet
spot: fewer tourists, tons of indoor activities, and shockingly affordable
hotel rooms. Friday and Saturday nights, in particular, can be absolute steals
on sites like Hotwire or Trivago. (Sunday through Thursday can be pricier
thanks to business travelers—but that’s a problem for another trip.)
Here’s how I’d do it.
Thursday Evening: The Planning Sweet Spot
Pop open your laptop Thursday night and start stalking hotel
deals. This is usually when prices for a Friday–Saturday stay drop to their
lowest. If last-minute booking makes you nervous, reserve a fully refundable
room at full price as soon as you’ve decided on a weekend—then cancel it once
you score a great deal.
While you’re at it, Google “NBC Studio Tour” and book
tickets for Saturday morning. Trust me, it’s worth locking that in early. More
on that in a bit. Once you’ve read below there are other adventures you may
want to book in advance, such as SUMMIT One Vanderbilt (see Saturday
night, below).
Friday: Broadway, Burgers, and a Legendary Bar
Head into the city and check into your hotel around 3:00 pm.
Freshen up—but don’t linger. You’ve got theater plans.
Make your way to Times Square and the TKTS booth at 49th
Street to grab discounted Broadway tickets. This time of year, most shows
(sorry…probably not Hamilton) are available at 25–50% off, and
half the fun is seeing what’s available.
Before the show, it’s cocktail time—and since you’re in the
theater district, you must stop at Sardi’s on West 44th Street.
The walls are plastered with caricatures of Broadway legends, and it feels like
stepping into theatrical history. A word of advice: don’t eat dinner there (the
food is…not great, in my humble opinion). Instead, walk in, head up the stairs
to the right, and settle into the second-floor bar, which overlooks 44th
Street and two of Broadway’s major theaters, the Shubert and the Broadhurst.
Fun fact: the second-floor ladies’ room is where
Tallulah Bankhead, a major stage star of the 1940s and 1950s and a big
personality, once found herself in an adjacent stall to another woman—both
without toilet paper. Tallulah famously called out through the partition: “Well,
if you don’t have any tissue, do you have two fives for a ten?”
For actual sustenance, duck around the corner to Iron Bar
& Grill for a solid burger or a personal pizza. Then it’s showtime. Tip:
double-check your curtain time—Friday performances aren’t always 8:00 pm
anymore. Some start at 7:30 or even 7:00.
After the show, you can hunt down a nightcap—or do what I
often do and happily crash back at the hotel.
Saturday: Studios, Sandwiches, and Skyline Views
After breakfast, head to Rockefeller Center for the
NBC Studio Tour. Nothing tapes on Saturday mornings, which means you get full
access: the Tonight Show studio where you can stand on the exact spot
where Jimmy Fallon delivers his monologue, and sometimes even a chance to sit
behind Seth Meyers’ desk. You’ll also look down into the Saturday Night Live
studio—and if there’s a live show that night, you may catch rehearsals.
Is it intellectually enriching? Not really. Is it fun?
Absolutely.
Since you’re already at 30 Rock, head downstairs to the ice
rink level (yes, that world famous ice rink) where there are plenty of dining
options. My go-to is Alidoro for one of the best Italian sandwiches in
the city. Simple, perfect, and exactly what you need.
From there, choose your own adventure:
- Top
of the Rock has some of the best views in NYC—but I usually save it
for warmer weather and clear skies.
- Ice
skating at Rockefeller Center is iconic…and wildly expensive. You’ll
pay an arm AND a leg. Walk a few blocks to Bryant Park, where
you’ll pay an arm OR a leg instead of both.
- Museums
galore:
- MoMA
is an easy walk and a classic.
- The
Met is a quick cab ride and great for a broad, immersive experience.
- The
most family-friendly option? The American Museum of Natural History,
also a cab ride away.
Saturday night is a wild card. Another Broadway show? (I’ve
been known to see four in one weekend—Friday night, Saturday matinee and
evening, Sunday matinee—but that might be a bit ambitious.)
A great alternative is dinner at Pershing Square,
right across from Grand Central Terminal. And you must step
inside the station—stand in the vast main hall, look up at the celestial
ceiling, and just take it in.
After dinner, spend a couple of hours at SUMMIT One
Vanderbilt. This isn’t just an observation deck—it’s a full-blown immersive
experience with mirrored rooms, glass floors, and jaw-dropping views that make
you feel suspended over the city. It’s dramatic, slightly surreal, and
especially magical at night when the city lights are blazing.
Sunday: Dim Sum and One Last Curtain Call
Eat light in the morning—you’ll want room by noon. Take the
subway down to Chinatown (your hotel can point you to the nearest line
heading to Canal Street) and settle in for a classic dim sum lunch.
My go-to is Ping’s at 22 Mott Street, but
honestly, it’s hard to go wrong anywhere in Chinatown on a Sunday afternoon.
The energy alone is worth the trip.
What happens next depends on your stamina—but if it were me,
I’d head back to Times Square, hit the TKTS booth one last time, and squeeze in
one more Broadway show before heading home.
Cold outside—sure. But Manhattan in winter—warm, lively, affordable, and endlessly entertaining—absolutely.