Stereotypes are often based on some reality. In the case of Greenwich, the preppy stereotype definitely applies.
As such, nightlife in Greenwich matches its target demographic. If you’re looking for raging night clubs or bars open later than 2am, the Gold Coast of Connecticut is not the place for you.
But as far as things to do in Greenwich, Connecticut, at night, there are still plenty of options. And not just for people looking for a dressed-up, fancy occasion, either.
Here are our typical recommendations for guests at Stanton House Inn, curated according to the vibe you may be searching for while here.
We also added some choices beyond Greenwich’s borders. After all, no location in Fairfield County or Westchester County is too far from downtown Greenwich.
How best to enjoy the nightlife in Greenwich, CT
Downtown Greenwich is more of a dinner and drinks atmosphere as far as nightlife is concerned.
Of course, there are other options, like movie theatres and art galleries. But you can see a movie anywhere, and many of the art galleries close the same time as shopping stores do, around 6 PM.
Artistic Things to Do in Greenwich at Night
Not to say those aren’t fun things to do here before or after you grab dinner and drinks.
Check out our guide to Greenwich art galleries if you’re interested in planning an artistic tour of Greenwich Avenue.
Where to go out if you want to get Dressed-up & Fancy
This is the type of evening for which Greenwich, Connecticut, is known. And if you are celebrating a special occasion or just feel like dressing-up and ignoring the prices on the menu, Greenwich will not disappoint.
Our top recommendations in town are the epitome of upscale dining, either on the waterfront of Greenwich harbor, or a refined country French atmosphere.
While the dining portion of the building is closer to I-95, traffic noises typically won’t distract you if you’re enjoying a drink or dinner out on the patio. And the service and food at L’Escale Restaurant in Greenwich, CT is splendid.
Even if you’re not in the mood for dining here, I would still recommend at least grabbing a cocktail on a nice evening before heading somewhere else on Greenwich Avenue.
Situated on the center of Greenwich Avenue, Bistro V offers a fantastic wine selection to go with its upscale bistro fare.
Places to eat and drink with a cozy atmosphere
When guests are looking to find a more down-to-Earth, homey feel when they go out, below are my recommendations. These places are more casual, but often not as high-energy as some of the other choices on this list.
Steam replaced a Chinese takeout restaurant that previously occupied the same site.
Town gossip claims that the previous occupants couldn’t meet health requirements.
But that’s definitely not a problem for Steam. Multiple Inn guests have returned raving that they enjoyed the best Chinese food they’ve ever found here.
This place is tiny, and the menu is limited, but that means that what they serve, they serve quite well.
The Ginger Man
Head back up Greenwich Avenue from Steam towards Stanton House Inn and pop into The Ginger Man for a nightcap.
The Ginger Man is a local staple, most people don’t even remember how long it’s been there. At this point, it feels like forever.
The vibe is an old pub, and there are more than a few pieces from the front door and further inside reclaimed from historic buildings in town that were demolished. Don’t miss the main entrance door (a former barn door), circular staircase, and the bar itself.
I recommend our local New England tavern for more than just the pieces inside, though. It has the best beer list in town, and the pub food is quite good.
And walking here from the Inn for a beer at the end of the day is only going to take you about 10 minutes.
Where to go for a fun, casual night out in Greenwich
I’m not going to lie, some of my favorite choices for this list are not in downtown Greenwich. In fact, a few aren’t even in Greenwich at all.
But Stamford and Port Chester are right next door in opposite directions. And the choices I’ve listed could be reached from their respective train stations, so you can easily imbibe without having to get behind the wheel.
And if you’re in a hurry, there’s always a taxi.
As the night progresses at all these places, the crowd gets larger, and the music louder. Hopping from each of these locations may be a lot in one evening, but you could theoretically start at The Spread in downtown Greenwich. After that, head over to BarTaco for dinner or a margarita, then finish the evening off at Barcelona in downtown Stamford.
The outside seating area looks back towards Greenwich. And nearby moorings make it easy for boaters to sail up, park their boats, and enjoy a cocktail or dinner overlooking the water.
Barcelona Wine Bar
We used to have a Barcelona in Greenwich, a few storefronts away from the Avenue on the Post Road. It closed after a fire, and didn’t reopen. There are a few nights I miss it, as it was a great place for late-night people watching when it turned into our only night club.
But the Barcelona in Stamford is even better. The nightclub crowd wasn’t always well-behaved.
Their happy hour menu is great, and they’ve got the same good tapas menu to go with their wine list. And its location on Summer Street makes it easy to go bar-hopping afterwards.
Options in Greenwich for Romantic Seafood Restaurants
I get requests for romantic spots with seafood a fair amount. And Greenwich has one of the best options on the Gold Coast.
And possible one of the most romantic restaurants in Connecticut, in our humble opinion.
Elm Street Oyster House
As the name implies, Elm Street Oyster House is just off of Greenwich Avenue on Elm Street. The ambience is cozy and romantic, and the seafood is phenomenal.
Can you find low-key, dive bars in Greenwich?
I had to add this section to a list of things to do in Greenwich at night, as it’s the most unexpected for those not intimately familiar with our town.
There used to be more tavern-style places in Greenwich and nearby, but they’ve become unicorns here. And I am intentional in calling them unicorns, as they’re a precious reminder of the working class neighborhoods that still exist and used to be much stronger in town.
Taverns, according to the state of Connecticut, are enclosed bars that are not obligated to serve food but can only serve alcoholic beverages with ABVs below 6%. I learned this out of curiosity during the pandemic.
Everyone in town (myself included) has memories of going to these dive bars with shuffleboards and cheap beer. And running into everyone else in town there, too.
These are really come as you are kind of places. Though I wouldn’t recommend coming from Thomas Henkelmann or L’Escale without changing. You may feel out of place.
Bruce Park Grill
This was the final Greenwich dive bar within walking distance of Stanton House Inn in downtown Greenwich. It was close to the Greenwich train station, up a hill and back down before the turnoff leading to Bruce Park.
Their pizza was well-known in the area. And I celebrated my 21st birthday here, enough said.
Two Door Restaurant
This is another local watering hole, still proudly standing in the Chickahominy neighborhood of Greenwich. It’s not far from downtown, but a half-hour walk or so is what you’d be signing-up for to get here.
Thursdays are chicken parmigiana night, and it’s worth the trip. But the bar scene is great, and meal specials on other nights are fantastic as well.
Sam’s Bar and Grill
This tiny little bar sits on the Port Chester side across the state line from the Byram neighborhood of Greenwich. Sam’s Bar and Grill‘s shuffleboard and juke box add to the ambience of this neighborhood restaurant serving American bar food.
This neighborhood dive bar in Stamford near Scalzi Park draws a loyal and local following. The relaxed atmosphere is perfect for enjoying their extensive beer and ale list and American comfort food.
Fiddler’s Green is Stamford’s Shippan neighborhood’s local bar. While the dart boards and pool tables are a draw, the food itself is what many people rave about, especially the chicken wings.
Date Night Ideas Near Greenwich, CT
If the above options don’t excite you, or you’re looking to go a little farther afield, there’s plenty more to explore.
Greenwich is in a prime location between both Fairfield and Westchester counties.
If you’re looking for a fist-pumping, night club-hopping scene, try nearby White Plains, NY, or downtown Stamford. I’m hesitant to make recommendations on that experience, as that’s not my personal idea of a fun night out.
How to plan a date night out in Port Chester or Rye, New York
While it would take me an hour, I can easily walk from downtown Greenwich to the New York State border at Port Chester.
Not that I’d recommend it when going out, just emphasizing that the best things to do in Port Chester, NY, are close. Port Chester’s train station is the next stop heading towards New York from the station in Greenwich. If you’re planning on drinking, I’d recommend taking that route.
That same night, or any night of the year, the concerts at the historic Capitol Theatre in downtown Port Chester typically offer something for everyone.
A perfect date night out in Stamford, Connecticut
Before they close at 5 PM, head to Franklin Street Works to start your afternoon and evening out in Stamford. This contemporary art exhibition space and cafe hosts three to four art installations per year.
If you’re still feeling artistic yourself afterwards, head to Pinot’s Palette in the Harborview neighborhood of Stamford and take a painting class, glass of wine in hand. Even if you’re not very creative, or artistic, or talented; the wine will help.
The Avon Theatre overlooking Stamford’s town green on Bedford Street is a viable alternative if you hate the idea of making poor imitations of other people’s work. This historic landmark of a movie theatre shows classic, independent, and documentary films.
The Palace Theatre is a better option in downtown Stamford for live entertainment, like comedy shows.
If you’ve already checked-out Barcelona on Summer Street, there are plenty of other great restaurants in Stamford. One is Brasitas, an upscale Pan-Latin restaurant with tropical decor. Cafe Silvium is a fantastic Italian restaurant that usually has a long wait for understandable reasons.
After dinner, check out the bars along Summer Street, Bedford Street, or around Harborview for a nightcap.
A date night out along the Hudson River
I love the towns that line the Hudson River in New York, from the village of Tarrytown, NY, all the way up north.
Not that my date night recommendation is going to go that far, but this is a farther drive than the previous choices.
That said, this date night is a great end to an afternoon spent on hiking trails in Rockefeller State Park Preserve, as the activity options circle around the park.
If it’s not too late, head over to A Maze in Pottery in Briarcliff Manor for a pottery class, or walk-in to paint your own pottery. It would definitely be a more unique and memorable date night activity, and you’ll have a memento to remember your visit.
Afterwards, or instead if this suits you more, head to Captain Lawrence Brewing Company. They’re a micro craft brewer in Elmsford, New York, that offers tours and tastings, as well as food.
Stay there for the evening, or head to Tarrytown and enjoy the hip dining scene overlooking the Hudson. The Main Street offers a wide range of choices from cozy taverns like Tarry Tavern to contemporary Italian-New American cuisine at Bistro12 to farm-to-table menus at Sweet Grass Grill.
You’ve finished the list of things to do at night in Greenwich. What about during the day?
Congratulations! You now have the tools you need to plan a great night out, or the perfect date night in Greenwich.
What about during the day? There are even more options during daylight hours:
- From learning about Greenwich history where it happened
- To perusing the shops and stores in the Greenwich Avenue shopping district
And exploring the many outdoor activities in Greenwich, Connecticut:
- From the various hiking trails near Greenwich
- To the best beaches near Greenwich and the best beaches across Connecticut, if you’re down for a day trip
Check out our complete guide to the best things to do in Greenwich, CT, and download our Visitor’s Guide if you’re planning a getaway here.