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Penny's Bar & Grill

4.5 (93 reviews)
Open • 11:30 am - 2:00 AM (Next day)
Updated 1 week ago

Services - Penny's Bar & Grill

Bartending services

Catering services

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PENNY'S BAR & GRILL ATMOSPHERE

What's the vibe?
DJ
Live music
Classy
Happy hour specials

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Recommended Reviews - Penny's Bar & Grill

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Jessica V.

Alessa has been open for about a year and a half. Right next to their sister restaurant Juniper, it's a quick walk from penn station. We started with a pizza it had a crispy bottom and came out piping hot. I enjoyed but standard. Their big pizza oven is located right at the front of the restaurant. For my entree I got the beet carpaccio. I absolutely love beets and I especially love that they make the beets the star of the show. I hate when it's mostly greens with a sprinkling of beets. I opted for grilled chicken with it and the chicken was thinly sliced and tender. The herbed whipped ricotta was generous and the nuts provided a needed crunch. (I only took a photo of the pizza because I dug right into the beets right away)

The Bianca pizza with mushrooms was chefs kiss
Dragonlady L.

This is one to bookmark to return to being so close to Madison Square Garden and Penn Station! Loves the vibe and decor of the restaurant and space. Walk through the doors and feel the warmth and excitement and be transported into one of the most elevated casual spots to have Happy Hour (it's til 8pm!) and dine on mouth-wateringly delicious Italian fare + the Bomb in cocktails and wine! Hostess took us to the back of the restaurant to sit at a table for four as we made a Resy - but it was only 5pm and we wanted to be up front by the bar area with the high top banquette seats! So, we asked and were moved and it was so much nicer and highly recommended. My friends enjoyed their cosmos and martinis. I had an angels envy old fashioned and with dinner had prosecco. We ordered the Bianca pizza and added the $8 wild funghi and chives and it was SO GOOD! The kale salad with celery root and grapefruit was perfectly dressed. The house made meatballs with homemade ricotta and grilled bread for appetizers were light and perfect for sharing. For protein we chose the semi boneless, lemon caper chicken and it was sublime!! Crispy skin. Juicy chicken and would definitely go back just for that! We headed to the Garden Cup for tennis and now I know where to go for any other MSG events that fits the budget and bill for many appetites!

Cheese pizza
Dave F.

After a long day of walking, we were craving some good food. Yelp suggested Alessa Cucina and Bar. The restaurant itself looked neat at the greeter at the door was very polite and welcoming. We sat down and ordered a few pizzas. These pizzas were legit. The mozzarella was fresh...not that grated stuff that comes commercially in the bag...but freshly sliced mozzarella. The pizza had the perfect balance of crisp and chewability. It was delicious. The staff were awesome. Our waiter was on his game. He came prepared with suggestions and also kept the drinks topped off. This place is a great place to hang out, take a date, or bring the family. It's not loud, and there is plenty of seating. If you're in the area, this place is a great find!

Cocktail menu
Radha P.

We went for happy hour, arrived 4pm and were charged full price. Which we paid and didn't bother with making it an issue. The waitress hurried us to take our order for shots because she said she had to get to her other table and rolled her eyes while leaving because she asked we wanted her to a picture of us and we said "no thank you" and did a selfie out of respect for her time! She constantly rushed us and I can't say I will ever return

Limoncello with grapefruit bitters
Ginger A.

We stumbled upon this beautiful and spacious eatery on our last night in NYC! Our server Thalia was patient and wonderful!! The staff there including the bartender and hostess were outstanding! We ordered the Salmon with broccolini and the creamy risotto!! The salmon was fresh and cooked perfectly! The risotto with the butternut squash was creamy and very flavorful!!! We had the best time here!

Dozen Oysters
Jacky C.

A solid spot for dinner for date night, work event, or just to catch some sports game at the bar. The interior design on this restaurant is elegant and the light is a bit dimmed to set the said date night mood. Service is fantastic throughout the experience as well. We started off with the Housemade Focaccia ($10), which comes with a cacio e pepe butter. It's their top selling appetizer and it's worth ordering. We also got a Dozen Oysters ($38). For about $3.20 per oyster, may be overpriced, but for those who really insist on getting it, the oysters are fresh. For entree, we ordered the Bucatini (35), which is a littleneck clams pasta dish in a white wine sauce. What really stood out to me was the Bistecca Tagliata ($48) aka a 12 ounce hanger steak. It's pricey, but worth ordering, just make sure it's medium rare. This comes with a side of cooked tomatoes still on its vine. Yeah, don't sleep on these tomatoes either as they're great.

Bianca pizza with fungi
Chip P.

Fantastic Italian spot conveniently located near Penn. We were headed to a concert at MSG and went here for some pre-show eats, and they didn't disappoint! The inside is beautiful, roomy, and the service was great. Waiter was attentive and friendly, and manager came by and spent time chatting with us. For the foods the Bianca white pizza with fungi is a must try. Good portions, and delicious taste. Chicken parm was also really good, although at the price it felt a little skimpy alone on the plate. We got the broccolini as a side, but it would plate nicer if they included some pasta no matter what. The meatballs were good, olives were a nice accompaniment. All in all I highly suggest if you need som nice Italian near Penn!

Salmon and broccolini
Briana W.

This was a delicious meal! Highly recommend visiting for dinner. Happy hour at the bar has great prices. Service was great! Conveniently located near public transportation. Ambiance was beautiful.

Negroni
Adam R.

Ratings are a little overstated imho. Nice venue convenient to the Garden and NY Penn. Bar is decent with good happy hour deals. Place was quiet but nice place to meet a friend or date. Food is good, had beet salad and arancini to start. Shares salmon and cavatelli for dinner. Respectable meal and friendly service.

Rigatoni w/ Short Rib.
Emma G.

This neighborhood is admittedly not the best, teeming with vagrants and tourists alike, but the one upside to a truly miserable weather day is that almost no one is out on the streets. I spotted this place on a lunchtime walk a few weeks ago amidst a bunch of depressing sweatshop-esque establishments and had a feeling about it. Last night on a chilly, rainy Thursday, I was able to procure the assistance of my Skipper for a dinner excursion to get a lay of the land right after work. Alessa's biggest selling point is probably the interior space; it is VAST, which is actually very helpful during the dinner rush. It was decently packed in there but it didn't feel remotely claustrophobic because all of the tables are set far apart from one another - not exactly a characteristic of the typical NYC restaurant. We were at a high top table on the opposite side of the room from the bar, and while the acoustics were a LITTLE eh (a few times I had to lean over to hear the Skip), it wasn't too bad. And beyond the spacing, it's very edgy in there with a modern European vibe in certain areas, but also the hint of a mahogany cigar bar situation. Interesting, and I'm not surprised based on the reviews how many networking events take place here as well. It seemed immoral not to hit up the pasta section of the menu (though the pizza ovens in the front look super legit), so I opted for the Rigatoni w/ Short Rib. Very tasty entree. The short ribs were cut up into bite size chunks, which I didn't mind - I'm used to longer/larger hunks, but it probably made me look like less of a savage animal as a I plowed through the meal. Ricotta isn't always my favorite, but I thought it worked here. Decent portion and something I would 100% get again. Italian cocktails are my least favorite on earth (I think they all taste like the bottom of a shoe and I don't understand why the negroni even exists at this point) so I usually go with wine at an establishment like this. I went with a pinot grigio; a little pricey for the size at $18 (definitely a minimal pour too), so hard to justify that as a recommend. There were one or two $16 glasses, but they were more in the Moscato vein, which is not my jam. If you have the desire/option, I'd probably go somewhere else nearby for a cheaper nightcap. The service was okay. Our waitress was nice but in my opinion didn't stop by enough. (The Skipper was more ambivalent about the situation) Towards the end, we were debating a second drink there or going nearby for another one, and asked her to come by in five minutes. She showed up again between 10 and 15 minutes, which in and of itself ended up being a big determining factor in our plans. It's definitely open to interpretation though; the Skipper had the better view and said she was pretty busy with a lot of tables. So your mileage may vary on that. Really liked the atmosphere and pasta - might not get into the weeds with anything else, but arguably what else do you need?

Shannon S.

I went art gallery hopping one Thursday night and was craving Italian after an evening of culture and socialization. I found Alessa nearby and decided to sit at the bar for a little solo dinner. I immediately loved the vibe of the restaurant, with wood and gold accents, very spacious dining area, and vibrant bar. The bar seating was comfortable and had purse hooks, which is always appreciated. I ordered an espresso martini and the cavatelli. They were playing a variety of sports games on the TVs over the bar, but I just turned on the NFL football game (Amazon Prime TNF) on my phone. The cavatelli was absolute perfection. The pasta was cooked to the perfect consistency and texture, and there was a plethora of mushrooms that were so juicy and tender. The arugula pesto was a really nice addition to the dish and not overbearing. I ate the entire thing and nearly ordered a second plate to go, it was so good! The bartenders/staff were so friendly and personable. I could tell they really valued connections with all patrons sitting at the bar. Overall, had a lovely dinner at Alessa, and I look forward to coming back soon!

Beet salad and I added shrimp - 11/18/2025
Natasha F.

Me and my husband both had a wonderful early dinner here and won't hesitate to come back - the service, food and ambiance were both top notch! the restaurant got crowded at about 6pm with people standing by the bar area due to happy hour and it got a bit loud to have a conversation. Dessert was phenomenal we ordered the tiramisu to share and it looked like a cupcake glazed in chocolate! My beet and goat cheese salad was soo fresh I loved it. I also ordered. My cavatelli pasta with wild mushrooms arugula pesto did not disappoint! I loved that our waitress brought out the dessert menus without us having to ask!

Free housemade chips with a happy hour drink
Bret F.

Love coming here for happy hour which is 4-8pm. The cocktails are always delicious and the staff so friendly! Free housemade chips with a happy hour purchase. Beautiful big space. Plenty of room to find a spot! Cheers!

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Penny's Bar & Grill Reviews in Other Languages

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Blake started us with a nice foamy espresso martini and margarita. Both prepared by a bartender who…read moreknows what he is doing! Here for USOPEN and had TVs in bar set to Open. Seasonal salad was exceptional.beets arugula and had some crunch with quinoa fried. Superb Mussels with chorizo had a nice kick and toasts garlic bread right on Thought we were going to a sports bar. Yes it is but so much more. Fantastic.

Step into the new 3 Monkeys, a tri-level playground of grit and glamour -- exposed brick that looks…read morelike it survived Prohibition, tin and copper ceiling tiles that wink under amber mood lighting, and a wooden bar polished by a thousand high-fives. Surrounding TVs keep every play, fight and miracle replayed in glorious surround-sass while wooden tables beg for pitchers, pretzels and conspiracy theories about the ref. Whether you're upstairs for the 3rd floor vibe, mid-level for the perfect sightline, or down in the cozy den with the best acoustics, this is New York sports bar energy: loud, a little brazen, impossibly welcoming. One particular bartender, Delaney not only brings an awesome level of energy to the bar, she saunters in like a halftime show -- a grin that's equal parts mischief and welcome. She's all quick elbows and quicker comebacks, the kind of bartender who remembers your name, your drink, and that one ridiculous story you told months ago. Her laugh is loud, her wink is devious, and she has a way of making first-timers feel like regulars by the second round. Behind the wooden bar she's choreography: expert pours, theatrical muddles, and a flourish that makes every order feel curated. Delaney's drinks are personality-packed, with her behind the bar, the place doesn't just serve drinks -- it gets its personality back. It's a place off 8th ave where fitness meets fun, and every corner feels like home--complete with friendly staff who know your name (or at least your size) and are always ready to offer a witty comeback or a perfect recommendation. Cheers!

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We had scored an awesome street parking spot and there was no way we were giving that up, so hubs…read moremade sure wherever we ate was within this area. We reserved for a quick bite at Redeye Grill before catching Dog Day Afternoon on Broadway, but as soon as we walked up, some bouncer told us they were closed for a private wedding reception. We were dazed and confused because how was I able to reserve online? But the real plot twist was that it ended up being the best thing that happened. We actually stumbled into Tanner Smith's thinking it'd be the typical, boring bar-food spot. Nope. They first sat us at a hi-top by the door, but that wasn't our vibe, so we grabbed seats at the bar instead. Best decision. Our bartender, Josiah, was absolutely killing it. My cocktail had passion fruit, so of course I asked my usual question: "But is it real passion fruit?" He just nodded in agreement and that told me everything I needed to know. That drink was legit and had nice strength. The food was great too. My fish tacos were packed with fresh fish, the guacamole and salsa were chunky and full of flavor and hubs enjoyed his pastrami sandwich. I have no clue when we'll be back in Midtown, but one thing's for sure- we're sitting with Josiah again.

Drink of Choice: NA Hugo Spritz - this drink was great and refreshing for all the non-drinkers!…read moreThey also had a short list of NA drinks to try while here! For those who like a little drink with their food, during brunch they offered a number of brunch cocktails (bottomless) for $35 Food of Choice: I had the Truffle Mac and Cheese and a side of the za'tar cauliflower. Both dishes were great and filling. The cauliflower had a lot of bold flavors! The onion ring on top of the Mac and cheese was a nice touch. I couldn't really taste the truffle but I would still order the dish again.

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Penny's Bar & Grill - venues - Updated October 2026

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