Skip to Content

10 Epic Happy Hour Spots on the Upper East Side (That’ll Satisfy!)

Best wine bars New York City
Image Courtesy Five Mile Stone

Whoever coined the saying “two things in life are certain; death and taxes” should make a revision and add “and outrageous New York City prices”. Seriously, whenever I have out-of-town visitors I can’t avoid the dreaded earful about how expensive everything is. But at the end of the day, this is New York City, the place where people come to make things happen.

And if you’re frugal like me, you know just how important finding deals can be when trying to make it in the Big Apple. This is where I come in! In this post we’re going to cover the best happy hour spots the Upper East Side has to offer. So, without further ado, let’s cover the best Upper East Side happy hours!


Visiting New York City? If you haven’t decided where to stay (yet) check out our helpful guide on Where to Stay in New York City (The best neighborhoods for first timers +3 to avoid). Don’t have time? Here’s our favorite hotel in NYC, hands down.


Happy Hour Upper East Side

Table of Contents: Upper East Side Happy Hour Spots

Before we dive into this guide, please keep in mind prices and specials are subject to change at any time.


The Sefton

Website: The Sefton
Address: 1373 1st Ave., New York, NY 10021
Happy Hour: Monday-Friday 11am to 7pm

The Sefton on the Upper East Side is not just a great happy hour spot, but it’s also one of the best places for a good pint of Guinness. While they offer cocktails and wine, the real star is the straightforward brew. The bartenders at The Sefton are friendly, and I’d visit just for their service. I like sitting at the bar for some pleasant small talk and the full Irish pub experience.

The best part is the generous UES happy hour from 11 AM to 7 PM. Featuring $5 domestic bottles and $9 margaritas, you can spend a full eight-hour workday drinking booze at this Upper East Side happy hour spot (although I don’t recommend it).

Something to know: The Sefton is named after a horse that was seriously injured in the Hyde Park Bombings in London. The horse remarkably regained its health and became a symbol of defiance against terrorism, even winning Horse of the Year in 1982.


The Penrose Best Brunch Upper East SIde
Image Courtesy The Penrose

The Penrose 

Website: The Penrose
Address: 1590 2nd Ave, New York, NY 10028
Happy Hour: Monday-Friday 3pm to 7pm

The Penrose is famous for its delicious brunch, but it’s also one of the top happy hour spots on the Upper East Side. The bar has a cozy rustic vibe, and during brunch, it’s bright and welcoming. Regardless of when you visit, you’ll be impressed.

It’s one of the best cocktail bars in the area, offering a wide range of drinks. The UES happy hour special runs from 3 pm to 7 pm, offering $2 off beer, wine, and well drinks. One standout is their dirty-pickle martini—it’s unique and surprisingly tasty, even for non-pickle fans like me.

You should know that The Penrose is strictly 21+ after 8PM and reservations are only available for parties of 5 or more.


The Pony Bar 
Upper East Side happy hour
Image Courtesy New York Magazine

The Pony Bar 

Website: The Pony Bar
Address: 1444 1st Ave., New York, NY 10021
Happy Hour: Monday-Friday 4:20pm-6:20pm

The Pony Bar brings the Wild West to the upscale Upper East Side with its authentic saloon atmosphere. Starting at 4:20 PM, the Upper East Side happy hour spot offers $7 draft beer, well drinks, and wine, making it a steal. As the first NYC bar to exclusively serve American beer, you can sample brews from coast to coast.

The happy hour lasts two hours, providing ample time to enjoy the affordable drinks. On Mondays, the special runs all day, with $2 tacos alongside the discounted drinks and traditional bar fare like wings and nachos.


Stella & Fly 
Upper East Side happy hour
Image Courtesy Stella and Fly

Stella & Fly 

Website: Stella & Fly
Address: 1705 1st Ave., New York, NY 10128
Happy Hour: Monday-Friday 3pm to 8pm 

Stella & Fly operates as a cozy cafe during the day, but in the evening transforms into one of the best wine bars on the Upper East Side. The neighborhood bar has become a local hot spot for an after-work drink. When most folks think of a wine bar the image of a relaxing and quiet establishment often comes to mind. Stella & Fly is anything but, thanks to a loaded schedule full of trivia, open mics, and live music. 

For those of us who are always on the lookout for a good deal, Stella & Fly has plenty. Wine Wednesday offers $9 wine all evening, and Cocktail Thursday has $10 drinks. This Upper East Side happy hour spot is worth making a detour for since the same pricing applies from 3-8 PM Monday through Friday.


The Five Lamps

Website: The Five Lamps
Address: 1586 York Ave, New York, NY 10028
Happy Hour: Monday-Friday 4pm to 7pm 

Created to “feel like home” The Five Lamps has curated an atmosphere that makes it easy to lose track of time. The bar has plenty of seating and the waitstaff is so welcoming they can begin to feel like roommates. 

The Five Lamps is one of the best Upper East Side happy hour spots if you’re looking to score a deal. You can expect $2 tacos and $6 margaritas on taco Tuesday (after 4PM) or enjoy a burger and a beer for only $20 on Wednesday.

If you’re looking to try your hand at trivia you need to head to The Five Lamps. Every Thursday at 7:30 PM the bar hosts the NYC Trivia League for good ol’ fashion neighborly competition (prizes for 1st, 2nd, and 3rd place teams).


Five Mile Stone

Website: Five Mile Stone
Address: 1640 2nd Ave, New York, NY 10028
Happy Hour: Monday-Friday 3pm to 6pm

From the outside Five Mile Stone looks like a restaurant you’d find in New Orleans. The two-story bar has a balcony that swells with animated locals in the summer like a scene straight out of the French Quarter. 

The bar offers an impressive 24 rotating craft brews on tap making it one of the best happy hour spots in the Upper East Side for beer-enthusiasts. The selection goes beyond local breweries too, there’s plenty of international beer up for grabs.

If whiskey is more your speed Five Mile Stone offers plenty, the bar has a staggering 90 different whiskeys for you to try. The joint also lacks the whiskey-snobs (often found at tasting rooms) so the vibe is easygoing and laid-back. This UES happy hour spot consists of a menu made up of delicious drinks and select $7 appetizers. At Five Mile Stone, you’re able to leave with a buzz and not have to break the bank.


Canyon Road
Upper East Side happy hour
Image Courtesy Canyon Road

Canyon Road

Website: Canyon Road
Address: 1470 1st Ave., New York, NY 10021
Happy Hour: Monday-Friday 5pm to 7pm | Saturday & Sunday 12pm to 7pm

Canyon Road has been around since 1985 and has served the neighborhood with one of the best happy hours on the Upper East Side. A place where locals can gather after work to unwind and visitors can find temporary reprieve. In 2016, Chef Ruperto Ramirez took over ownership and with that created a menu of authentic Mexican food, an ode to his upbringing.

This Upper East Side happy hour spot offers classic Mexican dishes like tacos, flautas, and quesadillas for $10 along with margaritas, sangrias, and buckets of beer for a reasonable price. That’s right, you can get a party bucket of beers (made up of 6 beers) for $25 to share with the table! Service is exceptional at this UES happy hour spot and the drinks are made strong.


Serena’s Wine Bar

Website: Serena’s Wine Bar
Address: 1268 2nd Ave, New York, NY 10065
Happy Hour: Monday-Friday 12pm to 7pm | Saturday & Sunday 12pm to 3pm

Wine just tastes better at Serena’s Wine Bar, one of the top happy hour spots on the Upper East Side. With an extensive wine list catering to every palate, and friendly, knowledgeable staff, it’s a perfect place to unwind on a sunny afternoon. While the focus is on drinks, don’t overlook the delicious food; their flatbreads and pasta are exceptional. For smaller bites, try their charcuterie meats and cheeses. The laid-back atmosphere makes it tough to leave this UES happy hour spot.


Pil Pil

Website: Pil Pil
Address: 265 E 78th St, New York, NY 10075
Happy Hour: Monday-Friday 4pm to 6:30pm

Pil Pil is a great happy hour spot on the Upper East Side if you’re searching for a place that has a nice ambiance but is still casual. The Spanish restaurant has a relaxed vibe to it. Branches hang from the ceiling and there is a wall of wine bottles behind the bar that adds character.

The cozy, homey feeling you get when dining here makes coming back all the more enticing. That is largely due to the friendly staff who work here. Serving tapas and wine, this Upper East Side happy hour spot offers a small bites menu. Along with $6-$8 drinks during the week.

If at all helpful, I recommend ordering the Croquetas De Espinaca ( Manchego cheese & spinach croquettes) and the Patatas Bravas (fried potatoes wedges). I mean does life get any better than discounted drinks and fried food? Probably not!


The Jeffrey Craft Beer & Bites 

Website: The Jeffrey Craft Beer & Bites 
Address: 311 E 60th St, New York, NY 10022
Happy Hour: Monday-Friday 4pm to 7pm

If you’re on the hunt for the best happy hour on the Upper East Side for beer and seafood, I’ve got just the spot for you. During the weekdays between 4-7 pm, The Jeffrey offers $1 oysters paired with $6 draft beers, which is a steal in this pricey city. If beer is not for you, no worries. This Upper East Side happy hour spot also offers deals like $10 cocktails and $2 off-house wines.

One of my favorite things to do during the summer is snagging a spot outside on the backyard patio and sharing a beer with my husband. Although the food options are limited during happy hour at this UES joint, the real menu is made up of delicious bites and meals. I recommend trying the pho tacos (yes, you read that correctly) and the barrio dip sandwiches, the flavors are unmatched.


Best Happy Hours UES (Post Overview)

  1. The Jeffrey Craft Beer & Bites
  2. Pil Pil
  3. Serena’s Wine Bar
  4. Canyon Road 
  5. Five Mile Stone
  6. The Five Lamps
  7. Stella & Fly
  8. The Pony Bar
  9. The Penrose 
  10. The Sefton

Further Reading for the Upper East Side

Best Things to Do on the Upper East Side: 15+ Great Things to Do in the Upper East Side
Where to Eat on the UES: 15 Epic Restaurants in the Upper East Side
Best Brunch UES: 15 Flavorful Brunch Spots in the Upper East Side
Where to Score a Deal on the UES: 12 Epic Happy Hour Spots on the Upper East Side
Restaurants Near Central Park: The 20 Best Restaurants Near Central Park

More Great Happy Hour Spots in NYC

Times Square Happy Hours: 10 Tempting Happy Hours in Times Square (You’re Sure to Love)
SoHo Happy Hours: 12 Satisfying Happy Hour Spots in SoHo
FiDi Happy Hours: 20 Sensational Happy Hour Spots in The Financial District
West Village Happy Hours: 10+ Wonderful West Village Happy Hour Spots (You Can’t Afford to Miss)


Map of the Best Happy Hour Upper East Side


I hope you enjoyed my personal list of the best happy hours in the Upper East Side. Let us know if you think we missed a spot.

Cheers!