Located right next door to the Paramount theater, Gleason's has a wicked cool vibe, yummy cocktails and good food. There's a big stage and fab lighting throughout...looks like a great place to enjoy some live entertainment. We went before a (Paramount) show and sampled the pizza, Brussels sprouts, wings and specialty cocktails. Our friends had pasta dishes that received rave reviews. Service was very friendly but since it was on the busy side, the food took a little while (which was totally fine since we had plenty of time before the show started). Really enjoyed my meal and I'll be sure to visit again. read more

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I really like this place! Food is always consistent and drinks are always delicious. We got the pear salad special, which was spectacular! For entrées, we ordered the swordfish special and the chicken Parm over spaghetti with vodka sauce. Both were excellent. Our waiter was a doll! Really nice and deficient. And to end this great meal we had that warm chocolate chip cookie with ice cream. Just delicious! It was a lively atmosphere and everybody enjoyed. read more

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Tucked away under street level in downtown Peekskill is a little Italian restaurant called Gleason's, and this little gem does not disappoint. We tend to follow the local cover band Run For Cover, and with them talking about this place on their podcast, we decided to make the drive from Connecticut to go see them play here. We came for the music, so I'll mention the stage first. I'd say there isn't a bad seat in the house, but there are. You can scoot your chair, though, so I'll say there isn't a bad table in the house. Acoustics are nice, and the stage lighting doesn't usually move around and shine directly into your retina. Table service keeps the food and drink coming so you don't miss a minute. Now, onto the food. Their pizzas are made from scratch with their house-made sourdough starter, and it sounds like they do a better job of keeping it healthy than I do. (I wonder if I can take some home. I should ask next time.) The result is a pizza crust that is light and airy, but is dense enough to provide what The Sporkful calls "toothsinkability." They don't put the kitchen sink on their pizzas, so don't expect the crust to flop over the entire time you're holding your slice. There are plenty of special pizzas, or you can build your own. Each one has a fully-cooked but not burnt crust, pretty close to the classic New York style that's an hour south. It's hard to resist a good pizza, so we haven't tried too much of the rest of the menu. Our forays into the appetizer section have been great, and the dishes I see pass by all give my eyeballs a feast. The craft beer selection is a little thin, with a list of five or six regional ones scrawled in chalk on one wall. Still, if you like IPA's, lagers, or ales, you should find at least one you'll like. Street parking can be a pain, but there is a parking garage a few blocks away that's free at night. EV owners, you'll have to fight over a double-corded L2 ChargePoint station around the corner. (Get with the times, Peekskill!) Fortunately, I think it's free for the first few hours, so consider yourself lucky to get a plug! read more

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Shrimp scampi was terrible. Not hot very salty and over spiced will not be returning.

Would not go back. Service and food was a disappointment. Went there before the Paramount concert 11/1/25. Ordered the plain red based pizza with crispy eggplant and light cheese. The pizza was a blob of cheese, with no flavor and a scant amount of sacue. The service experience regarding the wings. I ordered buffalo with ranch dressing. The wings arrived with blue cheese which I don't like and can't make do with it. Waited a good deal of time to catch our waiter's attention to ask for ranch. Once ordered it was a solid twenty minutes to have the ranch dressing arrive. Once the dressing arrived, I asked the waiter to reheat the wings (through them back in the fryer if that allowed, microwave OR MAKE A FRESH ORDER since only two had been eaten while holding out for the ranch dressing. The wings come back in a different bowl but they certainly were not hot. I should have said take these off my check since this is not how wings are to be eaten (COLD). In total, the wings sat on the table for 30 plus minutes waiting for the ranch dressing and reheat. I had one draft beer and asked the bus person to get us two waters. He never brought them. We did get them from the waiter. There is more. I wrote to the restaurant to politely share my experience through their website. The response included an offer for a free meal but never came through on that offer. read more

I already left a review. We waited 30 minutes for a drink, although there were 2 bartenders, and an hour for our food because there was only one waiter who was doing his best but the place was full. We had to eat as quickly as we could in order not to be late for the show next door. And one of the orders was wrong but we had neither the time nor the heart to say anything at that point. This restaurant had everything for it, location, ambiance which was why we had given it a second shot. They have really blown a great opportunity. We won't be making the same mistake again. read more

Great bar in Peekskill, the bartenders April and Aaron run a well-oiled machine...trivia and karaoke Wednesday and Thursdays are really good and the weekend it's the place To be ....don't miss out on this place read more

Our server Chazz was excellent. He went above and beyond to try to keep multiple tables happy. The pizza was very good and had many interesting options. The only down side, as many reviewers have mentioned, is the time to get your food. Looked like almost everyone there was having dinner before a show, so there was a huge influx of customers all at once. Obviously this puts a strain on the kitchen and they did their best. Overall I would definitely go back but will be sure to get there early, or on a non show night. read more

Unstocked bar (no white wine and poor liquor selection), terrible service (took 4 visits to order), awful food (oil, red pepper flakes, too much garlic). Go somewhere else while you're in town. read more

Gleason's is in a great new bigger space. Their food is still spot on, as is the service. I had the Carnivore pizza with no cheese and shared Thai chili wings. Bothe were very enjoyable and flavorful. The Thai chili is more sweet than spice. I also had the In-house bourbon and sloop juice IPA. The bourbon was a solid offering and had decent body and finish. Very oaky. Service was accurate and friendly. I'll be back. read more

Great pizza and pear salad. Good service and live music most of the week. Large restaurant, no need to make reservations

Used to be our go to spot in town, but the quality just keeps going down. The past few times we've decided to give them another shot, they prove it's time to say goodbye. Just got a $22 Caesar without dressing (aka a bowl of lettuce with some chicken) and a $20 half cooked pizza with depression era quantities of toppings. Hope they turn it around, but we're done waiting for it. read more

Service was terrible!!!! I went there tonight with 2 girlfriends before the Anthony Rodia show at the Paramount. We had a 5 o clock reservation to give plenty of time for dinner before the 7 o'clock show. I ordered eggplant parmigiana and spaghetti and had to chase around 3 waiters to get a spoon to enjoy my spaghetti and another 2 to get a sprinkle of cheese. No bread was offered and I asked several times, finally brought out as the check was brought out. The waitress responded with "we're very busy tonight ". Not my problem. My friends ordered a pizza and we shared wings and a bottle of wine. The only positive thing about the restaurant is that they're close to the paramount theater. They need to definitely get more help if they are going to continue to attract the pre theater audience. I for one definitely wouldn't rush back!!! read more

We stopped in for a pre-show meal before a concert at the Paramount. This is the perfect spot to do that, lots of good options. I went with the sourdough crust "Hot-cha-cha" pizza - red sauce, crispy chicken, hot cherry peppers, caramelized onions and mozzarella. The chicken was really good, the onions perfect, there's a good amount of peppers so lots of heat. I wish the crust was a bit crispier, that would be my only complaint. It's a very good pizza and filling. My wife went for the "Tupelo Honey" - whipped ricotta, pepperoni, mozzarella with a hot honey drizzle. She loved it. My brother went for the Smokehouse burger which didn't stand a chance, he finished it pretty quickly. My sister in law opted for the Mushroom and leek white pizza which she loved. Cocktails are good, they have some nice beer on tap too. It's a fairly large space with plenty of room. Live music happens on weekends too. Definitely a cool spot and we will be back. read more

So I made these reservations over a month ago. Had called ahead to confirm a good time to come as we had theatre tickets for 6pm. My group of 5 arrived and placed our orders within the first 15-20 minutes with our waitress. Drinks and food took in excess 45 minutes to arrive. When expressing concern to our waitress Sharon she advised that we hadn't ordered promptly enough - we had ordered when she finally came to ask for our order. Food was delicious but service was atrocious. Would come back only if no other plans were in place. The theatre is next door and we will still be late. read more

Cool bar/restaurant, good vibes from friendly bartenders upon entrance! Nice variety of choices. While delicious, the meatballs are small and the wedge/sandwich could use a couple more added considered it's price. Too much for its value. Now the were a different story, large, tasty salads! Also the wait was rather long especially considering that we were the only couple in there. The order was delivered wrong, chicken parmesan instead of meatball parmesan. After the mistake was made, it took literally 30 minutes for the meatball sandwich to arrive. Guess they had to make the meatballs. read more

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My fiancé and I came to Gleason's to celebrate his 21st birthday and because it was walking distance from home. We walked inside and a very friendly lady greeted us and took our cover for the band. What was very nice though was when my fiancé handed her his military ID, she gave him a discount for the cover. Very nice gesture for his service and made us feel very welcome. We chose seats at the bar and our bartenders were awesome. Very fast, friendly, and I always had a drink in my hand. The live music was a bit too loud and made conversation difficult. The drinks were good, generous on the alcohol. The wine was good as well. Overall, this is a very nice local place within walking distance, has good atmosphere, friendly staff, happy customers, respect for military, good drinks, and a great place my fiancé and I spent our Saturday night. We will certainly be back! read more

Delicious pizza and good drinks. Lyndsay was very polite and gave amazing service! Will come back

I love that I can get a vegan cheese pizza from Gleasons!! My hubby thinks their red sauce is a bit on the salty side but it doesn't bother me. I also usually enjoy their cocktails as well. The reservation system there is a bit flawed because last time we went the restaurant was completely empty and they told us to eat in the bar area. By the time we finished our meal there were still plenty of open tables so it seems like their timing / table expectations are a bit off. Sometimes it's super loud as well. Overall, I am glad to have a place so close to home that offers Vegan cheese! read more

Went here for Mothers Day and I wish I didn't. Well I'll preface this with if you want to be left alone and sit around this is the place for you. Unfortunately, I like the waiter or waitress to have a clue what they're doing and come to the table. 1. Walked in party of 4 and the host let us stand around for ten minutes before we were greeted and brought to a table, mind you as we stood in the entrance aimlessly several servers walked around and literally walked passed us numerous times. 2. Now we were seated and after 6-8 min here comes our waiter. She pours the water, and does not even ask if we want anything other than water to drink. My mother in law at this point asks for lemon for her water. She comes back moments later with 2 lemon wedges in a napkin in her bare hand. Now she's ready to take our orders with not a pen or piece of paper in sight. At this point, I'm like wow she must have a photographic memory. Sadly, that was not the case. She comes back to the table to ask us to remind her what we ordered. So now here come the beverages which were limited as we were told they didn't have certain things that were literally on the menu. 3. After close to 45 minutes not an ounce of food. We had to literally keep asking and no one came to the table in this time. Needless to say every single server looked miserable and treated patrons like they were being bothered. 4. We were starving and close to an hour the food comes out and it's wrong. Maybe writing things down isn't a bad idea and should be a practice put in place. When we told the waitress we were missing requested toppings she said she would bring some out in a cup. My father in law finished his pizza before she could bring the mushrooms that's how long it took. My husband, mother in law and self requested boxes for our remaining food. My mother in law at this time also ordered some tiramisu. It took over 25 min to bring the to go boxes, by this point my mother in law was like just make it to go because we didn't want to wait another 45 minutes.5. Now we ask for the check, this part took 30 seconds! We are getting close to finally leaving and I cannot wait but nope the wait begins for them to pickup the credit card. After 15 minutes the most inattentive looking individual returns to get the credit card. The card is finally returned and we can finally go! We made it through this cringeworthy experience of waiting around and not being attended to. The pros: I would be a liar if I said the place wasn't gorgeous, because it's modern & well decorated and the ambience is great! The location is great and there's plenty of parking. The food is delicious and well prepared. Alcoholic beverages are well crafted and tasty. The Cons: SERVICE is probably the worst I've ever seen, and they could benefit from a floor manager or some kind of direction because there is 100% potential to be a great establishment read more

Gleason's - Pizza - Pizza Near Me - Peekskill, New York

Visited this establishment last night (Fri 4/19) for dinner & to see a friend play in a band. It's a great venue, open floor plan, nice seating, decent beer/wine/drink list and the food was pretty good. Service was excellent but the food was overpriced at $300 for a party of 6-people when all we had was 3 pizzas, 2 salads & 2 drinks per person. If you do visit, def try to meatballs. They're excellent. read more

The restaurant was nicely fashioned. The food wasn't there for me. Perhaps I shouldn't have had the pizzas, as they werpiping hot and the toppings were run of the mill. read more

The Herb Moscow Mules are my fav! Love the bartenders & entertainment especially the band 'Run for Cover'! Great place to hang out, the penne vodka is delicious. read more

Gleason's - Herb Moscow Mule - Pizza Near Me - Peekskill, New York

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Good food and a really fun place. Wait staff is very nice. It is close to the paramount also.

Our group of four went to Gleasons for dinner last night before seeing a show at the Paramount. We've been multiple times before with okay service, but had a less that acceptable evening last night. 1: We walked in at 6pm, and didn't get our entrees until 7:40. Our show was at 8. 2: Two people ordered Jameson and ginger, but definitely did not receive Jameson (We're Irish... we know our Jameson). The bartender insisted we were served Jameson without offering a replacement or another drink. 3: Our simple order of 1 pizza, a poached pear salad and 2 burgers was incorrect. We received a beet salad instead, the pizza was incredibly salty. 4: The waitress was less than thrilled in helping us rectify the drink mishap, and was visibly aggravated that we sent back the incorrect salad. Additionally - It took her 30 mins to give us two additional place seatings /cutlery to make up for two missing when we sat down. We seemed to be a nuisance to her although we were polite and cautious about speaking up. Overall- it was not a comfortable, enjoyable experience - we will not return any time soon. read more

What a great date night at Gleason last Saturday. We sat at the bar and started with an aromatic Sav Blank and perfectly mixed Negroni along with the Mac and cheese croquettes. We settled on sharing a delicious pizza with a vodka sauce base, chicken cutlet, bacon, onions and mozzarella. Our bartender Luke was attentive and kind. He even gifted us a hat and sign from the owners own vodka distillery. We will definitely be back and soon! read more

Went here for a pre-show dinner. The menu is good. Husband got a personal pizza ($22!) that he said was good. I got fried calamari app and then chicken parm over pasta. The calamari was cooked perfectly, but they shake salt on it, which made it WAY too salty. The same with the chicken parm. Also, the cheese on the chicken parm was not grated mozzarella, but a square slice of cheese melted on top. I could not drink enough water all night long to quench the thirst from eating all this salt. Could have been awesome, but I won't be back. read more

Situated in the old Hudson Room haunt the now bigger & better Gleason's provides strong "Comfort Food" service. We stayed away from the signature pizza's instead opting for traditional menu items. The Crispy Calamari starter with both Thai chili and marinara sauce was a plentiful fine starter. The "Chicken Parm" sandwich / hero was large and fresh with perfect french fries. The Spaghetti & Meatballs was enjoyed as well. Again - portions are large here as you actually get what you pay for (which - these days - is not the norm). Service while friendly was a touch slow as we became forgotten at meals end. While we understand pizza is the thing here a few more outside the box menu items should be added. Overall Gleason's is fine comfort food and certainly worth a visit. read more

Food and drinks were incredible. Our waitress Nicolette was super knowledgeable and helpful. I highly recommend this spot!

Before they moved this place was great. Increased food & bev price has greatly decreased my interest in returning. Service is fine but your run of the mill restaurant. The stage is great for karaoke, but beyond that it just seems like an overpriced bar. read more

The worst service ever. You will wait 2 hours for your meal..whether pizza or shrimp cocktail. Plus they call and ask you to move your reservation to earlier to ensure you are accommodated and they still cannot get you food within 90 mins. Not the waiters fault. They do their best but kitchen staff is horrendous and they cater to Uber Eats and take out only. Leave customers seated waiting for hours. Do not bother. I have given then many chances. The worst!! Don't go if you want to see a show at Paramount! read more

Cozy bar with delicious and fresh food, pizzas, and a nice beer selection. There are so many varieties of pizza, we had the California and a special vodka and chicken and a plain for the kids. All were amazing. It was hard to decide, we can't wait to try more! We also ordered a Caesar salad and calamari as an appetizer and it was crisp and tender. Looking forward to coming back! read more

Gleason's - California Hot-Cha-Cha - Pizza Near Me - Peekskill, New York

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Always an enjoyable experience at Gleason's! First time at their new location and I love the ambiance! The food is always delicious and even with it being a busy night with an event going on, the service was excellent! read more

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I love Gleason's the mushroom pizza is so delicious. The service is always good. I highly recommend! read more

Gleason's - Pizza Near Me - Peekskill, New York

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Soooo I pre-ordered some food for dinner via yelp bc Gleason's has the 'order takeout' option. I set it for a 6pm pick up and was seriously looking forward to trying the dope shrimp and fennel pizza on the menu. Skip to 6pm when I had to park a few blocks away and walk in the rain to get my goods.. man this pizza better be worth it. Go inside and I'm greeted and said I'm here to pick up and give my last name.. hostess is confused but checks the back and then speaks w another waitress to which she tells me 'we don't do that on yelp only an outside company.' Ummm yes I know it's powered by grub hub and uber eats. No apologies no offer for me to choose something new for them to make me. Instead I was given a curt, no you are wrong attitude. Now I'm ready to have a serious Wayne's brothers B F. I was still charged $30 and change so I had to contact grub hub multiple times since the wait was so long. At 9:30pm Grubhub says they will call the venue and somehow, they said oh sry it's too late to make that order now. Wait WHAT?? So they lied about using yelp ordering? Wtf just give me my money back (and Grubhub did.) Never again with Gleason's after that what the frell poor customer service I received. read more

Gleason's - Acts as if my order was fulfilled but no dice - Pizza Near Me - Peekskill, New York

Great Pizza BUT the tomato soup is way to sweet, it should be tart and the tiramisu tastes like cool whip with cocoa

Great bar very friendly staff with lots of specials and themed days of the week one of my favorite places to drink. Great vibe overall. Food could be slightly better or better priced. read more

Food portions! That's the biggest this for me here! The portions are awesome! You don't feel like you're getting skimmed. The prices are great, spot is clean and put together nice and the workers are spot on with their service. I went here for my birthday because I wanted something not over the top but that I would enjoy and it certainly did not disappoint me! They will see me again for sure! read more

Gleason's is fun. Very hip vibe inside with cool music playing. We know their pizza's are good but if you explore their menu you'll find it's all good. I've had amazing steak and fish here. Cocktail menu is well above average. If I had to nitpick I would just wish for better craft beer options. read more

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We have enjoyed Gleason's food for years. We recently hosted our son's first birthday here and couldn't be happier. The Gleason's team was helpful from beginning to end. They allowed us to have a separate corner of the restaurant where we could decorate. We had a great pizza buffet with plenty of options. They helped us cut and serve our cake. Everything was top notch and our guests really enjoyed it. I would absolutely host a party here again. read more