I've been to 88 Charles street a few times already and each time the food is great the staff is even better and the ambiance is fantastic. It can be a date night, family get together or just dinner on a regular day. I always live hearing the specials and usually I'm not a specials kind of guy but there's always something in their specials that grabs my attention and is always delicious. If you're a steak person their steak is always on point. Good quality meat. The herb butter on the strip was the perfect compliment to the perfectly charred juicy steak. 88 Charles street has become a special place for us. Love it everytime we go. read more

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Was invited for a group dinner. Amazing.. good atmosphere... great food and great staff. I will come back for a more private sit down but they sure displayed a nice show for us! Great job- the chicken and steak was very very good!! read more

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I went to do a rake out at 6:30 pm Very few patrons. Bartender was great. Ordered a glass of wine and a menu I ordered the breast of chicken with mashed potatoes and spinach I paid $46.00 for a Chicken thigh and half glass of wine It was horrible. I did tip 20% because the bartender whom took my order was kind conscientious and extremely considerate I will not go back read more

88 Charles Street Restaurant - Chicken BREAST. Which is a thigh with skin on it And it said au jus it was jarred gravy For $46 and half glass of white Chardonnay - Italian Near Me - Montgomery, New York

Food is amazing !! Service is great everyone is friendly. Drinks are perfect!! Definitely going back!

Nice ambiance classy, modern & hip. The service is impeccable from the bus girl who is amazing, to the servers shout out to Kenneth. Then there's the Branzine specialist carver. Never have found the tiniest of bones after he played it. Expert! This is by far one of my favorite restaurants read more

Awesome restaurant! My boyfriend and I are visiting from out of town and happened to stumble upon this place. Our server, Ryan, was attentive, helpful, and accommodating. I ordered a modified Branzino dinner & my boyfriend got the burger. It was my boyfriend's birthday and they brought him out a cake with happy birthday written on the side. They even sang! It was so sweet:) I know if we ever happen to find ourselves in the area again, we will very much be back. The food was awesome & the service was even better. read more

88 Charles Street Restaurant - Italian Near Me - Montgomery, New York

Nice atmosphere. Service was rude perhaps because I'm not white and was spoken to very condescendingly which is why after ordering my appetizer I decided not to order dinner and went somewhere else where my money would would be appreciated with respect. Food was decent but again I only had the shrimp appetizer and a glass of wine, I did want to try their tomahawk steak however the service was rude so I decided to leave instead of continuing the bad prejudice dining experience. read more

88 Charles Street Restaurant - Wine - Italian Near Me - Montgomery, New York

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My family of 11 went for Easter dinner here. Everyone's food was bland, no seasoning at all. We let them know, but no reaction. I will not return. I'll redirect to ward's bridge inn next time. The waitresses tried her best, but I don't think they had enough staff. read more

The service was absolutely wonderful. I was visiting from Long Island and ordered the filet mignon. I have had filet mignon in manhattan and many other steak restaurants. This was clearly the best I have ever had. There was nothing that had to be cut off -- it was lean and tender and cooked perfectly. The gravy was very good. When I come back to visit my mom, I will be back. Thank you for an amazing dinner. read more

Another stellar night out! Had a drink at the bar with Liz, who is a fabulous and fun bartender! Then we moved to our table for dinner. Hubby had the NY strip (which he orders in many places and this is one of the best he's had in years) for dinner and I had the filet mignon, wild mushroom risotto! Both were amazing. He also had the cream of chicken soup and I had the Caesar salad and those were also enjoyable. Can't forget the honorable mention of the truffle fries with the NY strip that my hubby loved (as did I, the 2 I was able to taste ). All I can say is that the service, food and staff here are amazing. We overheard another table unhappy with their food selection - diner's fault who misunderstood the menu and didn't want any comp food, however the owner/mgr insisted to make it right and gave them a take home dish. I'd recommend this restaurant every time! No pics this time bc we ate too quickly. read more

Great food, waiter was awesome. They upgraded the place and it looks amazing! We didn't feel pushed out of the restaurant either. They let us take our time and enjoy our meal. We got apps and dessert too, no pictures though. I had the lava cake for dessert, it was great. We had the calamari for an app, also great and tender. read more

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The service was wonderful from the second I walked through the door. I love the decor. The food was delicious!! I can't wait to return!

Lost Charm, but still an enjoyable place. There is something to be said about upgrading an establishment, however, this trend of 'Urbanizing' everything in sight is getting out of hand. The charm that was once the Hudson Valley is quickly fading into a fond memory. Since the political pandemic better known as COVID, many of the more charming eateries in the Hudson Valley have fallen by the wayside. Weather reasons are because of lost revenue, or new management moving in from NYC, whichever it may be, there seems to be a prevalent obsession with making everything modern and cold. Not every restaurant has to look like an eatery in Chelsea, or in the West Village of NYC. In this particular case, I speak of my most recent visit to 88 Charles street in Montgomery NY. We were frequent visitors to this quaint eatery, that was until the COVID took a poop on every small business in all the Blue states. My group of friends, numbering about 8 adults in the 55-65 year age group would enjoy many a visit to this place. This past Friday we decided to check it out since it fell under new management and had been 'upgraded'. Gone from the place is the charm of an old-world Italian restaurant that was one of its most attractive attributes. All being Brooklyn-born and raised Italian Americans, we always found this place to have that familiar allure of a cozy family restaurant, ...not anymore. With that said, I must say that the quality of food was excellent. The service provided by the waitstaff was excellent. We were visited by the owner at least twice, he was an absolutely charming gentleman, ...and that was excellent. The quality of the food was excellent. The quantity of food per dish was perfect. For starters we had calamari fritto, it was o.k., nothing special, a little on the bland side. In addition, we had an order of grilled Spanish octopus. Again, we've had better, but it was still o.k. Now for the main dishes. I had the Stout Braised Boneless Short Ribs, and it was prepared to perfection. There were additional orders of Faroe Island Salmon, which was prepared to perfection, and the Chicken Milanese (Dinner Special) topped with tomatoes and mozzarella, which was also prepared to perfection. Then there was the order of Tagliatelle Bolognese, ...excellent in every aspect. Our desserts were caramel praline topped cheesecake, crème brûlée, chocolate lava cake with cappuccino ice cream, and an order of cappuccino ice cream. To order, they were absolutely succulent, tasty, and perfectly prepared. It is unfortunate that the newly renovated atmosphere of the 88 Charles St Restaurant cost them the fifth star. The once friendly, warm, and welcoming feel of a Tuscan-style eatery has been replaced by a cold, sterile, and unwelcoming place. Eating at the old 88 Charles street restaurant was like eating at your Italian grandmother's house, now it's like eating at some trendy yuppie place where people pronounce mozzarella (moz·za·rèl ) like 'motzarelley'. I'm NOT saying that the staff in any way is lacking, ...to the contrarry, they were wonderful. It's just the feel, or as the Chinese say ...the 'Feng shui'... is much too modern/urban for these old Italians. However, we will be returning, the food was excellent, but we'll just go somewhere else to relax for cocktails and conversation. read more

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Food was very good, ambiance was nice and the service was great. My wife grew up here and never had the chance to dine here and I was able to give her that memory yesterday and we loved every minute of it. read more

I don't understand what the big hype about this place. This would have been the 3rd time and every time I wonder why the heck did I go back. This last time was it for me! Who wants to be eating dinner while the employees are spraying chemicals and cleaning along side my table. Shouldn't that have been done prior to opening the doors. My daughter had the spareribs with mash and I had breaded chicken with a salad. Just ok. Thanks but no thanks. I should have gone to The Ward's bridge inn around the corner. read more

The food was ok. My husband got the tomahawk and I got the filet mignon. You would think with how much you pay it would have flavor. It was not bad but it had no flavor. The service was amazing! Or waitress was attentive and very well mannered. The bus boy and servers all very nice as well. We have every course a try had starters an entree and dessert. Nothing was anything special to write home about. read more

Everything was fresh and delicious! Our server was Matthew who had a great personality and delivered excellent service. The atmosphere was cozy and inviting. The perfect blend of rustic and modern. For appetizers we had the pork belly, entrees we had the short ribs and branzino special. The flavors, textures and presentation were on point. The cocktails were amazing, as was the dessert of fried bananas with banana Oreo ice cream. Can't wait to return, so much to try! read more

Very nice, local dining experience, excellent bar and very pleasant staff showed up without a reservation and they went out of their way to accommodate us in a timely fashion. read more

This place is a must for a special occasion. The food is outstanding. The tomahawk steak is a sight to behold.

Went here on 3/16. It was cute we sat outside and was kept warm by the heaters. The waitress was sweet but the food was not good Honestly. I'm wondering of the chef was off because another table sent their food back as well. Our October was bland and burnt and the filet mignon was overcooked and dry as well. Definitely wouldn't return simply because it felt like a waste of money. read more

First timer here. We had Ryan as a server and he was very knowledgeable of the menu and provided great service. We ordered the Tomahawk and it didn't disappoint. It was cooked perfectly and had great flavor. We opted to upgrade the onion rings to the truffle fries. . Also order the Wild Boar Belly for an appetizer and it was quite good. The restaurant its self has a nice atmosphere and layout. Definitely worth a visit if you're in the area. read more

88 Charles Street Restaurant - 48 oz. Grilled Tomahawk Ribeye Steak - Italian Near Me - Montgomery, New York

Always a solid place for lunch or dinner. The food is always great, as is the service.

Service was good but the food really wasn't what you would think it would be for the ambiance of the restaurant

Went here for dinner and some drinks with my cousin. The bartender Matt was awesome. Great old fashioned and a great atmosphere! Dinner was outstanding! The tomahawk ribeye was just perfect and what a presentation they do! Will be back her for sure! The gem of Montgomery! read more

88 Charles Street Restaurant - Lemondrop martini & bourbon old fashioned - Italian Near Me - Montgomery, New York

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Had an amazing meal there . Also best chocolate martini ever. The place is beautiful ... staff owners all super nice

Food, service, ambience! Great meal with an attentive staff. Big city meal in a small town setting. We will be back!

Was surprised when my silverware was put directly on the table rather than a napkin....bread portion was laughable and they never brought more....if you order a tomahawk steak or coffee later make sure you have plenty of time, it takes forever.....rather than ask customers how they parked their vehicles put some lines on the parking area or even a few signs.....definitely my last time at this establishment.... read more

My husband and I were in Montgomery for the Orange County Airshow. Luckily we went to this restaurant the night before the show. Food, service, ambience and cocktails were wonderful. We shared a Caesar salad which was fabulous - white anchovies and homemade crotons! My husband had the seared scallops and I had the sole stuffed with crabmeat. The presentation and taste was first rate. The fresh peach carmelized and sautéed with slivered almonds served with ice cream was a fitting finish to a wonderful meal. Matt our server made us feel like welcomed guests. What a great place! read more

Food was excellent to say the least and service was beyond attentive!!! Great atmosphere. Definitely a must do if you haven't gone !

Very hospitable with good food. Everyone in the party were more than satisfied with the entire experience.

food is consistently good. service is excellent ! ambiance is beautiful. love this place. read more

Definitely recommend at least once . Food and service was on the dime . Owner took time out to visit all tables and talk . I was impressed.

I came here for a birthday dinner. Since we were a large party we made a reservation. We were seated immediately and cocktails were delicious. It took so long for our entrees however (around 90 minutes after ordering), that we had to ask about updates from staff. They apologized stating the kitchen was backed up and tried to rectify the situation as best as possible. The staff was friendly and the entrees were delicious. I'd likely go again just not during a busy time or for a group celebration. read more

I got some good to go recently for lunch. The 5 of us all enjoyed our meals. We had a gluten free person and they were knowledgeable and helpful with suggestions. I felt that they understood our dietary needs. I didn't get to experience the service since we took the food to go but the phone ordering was very easy and the man who rang up our order was helpful and courteous. The inside looks great so I'm looking forward to eating inside next time. read more

Delicious steak. Good service. Love the covered outdoor seating. Great singer on Friday night 6-16!

Quality of food and service was beyond all expectations for what I would have thought would be in a small town. The veal chop parmigiana and the scallops over tagliatelle were the best I have tasted (both on the specials menu) - and compatible to the best restaurants in NYC and Italy. Simply wonderful! read more

First - We decided to go here to celebrate our 1st year wedding anniversary. We did this because we believed this was a quiet somewhat upscale establishment. We were seated in the outside area which on a cold January night was well heated and comfortable. We enjoyed watching the flames from the heaters. When we arrived for our 7:30PM reservation the restaurant was about 25% capacity. The food was outstanding. We ordered drinks and shared the Boar Belly Appetizer which was balanced not too salty and well sized. The menu is somewhat limited but what they do; they do well. I had the rib eye steak special and my wife had the salmon. The service was attentive without being pushy... so why only 3 stars? About 3/4 of the way thru our meal staff began rearranging tables at the far end of the area. A large group entered from every direction. They were extremely loud, using profane language and completely inconsiderate of the us and the guests at two other tables in the area. We mentioned this to our waitress who said she was sorry but lucky we were almost done. Never mind that we'd intended to order another after dinner drink, then have coffee and dessert, which we decided not to do because we couldn't hear ourselves speak. We spoke with the manager. He said they're regulars and he couldn't refuse to serve them and there wasn't room at the bar for them that they'd come from another party. He said had he known he'd have found a different table for us. I find this totally unacceptable that we would be moved on the middle of our dining. This place advertises and upscale and elegant. The manager needs to observe that guideline. If we wanted to eat at a bar with drunken patrons there are other numerous establishments to support. He offered to buy us a drink and dessert which we declined he again said they are local people what can he do. Well what he did was drive a local Couple away and we aren't the only ones. They couple across from us left disgusted by that same loud obnoxious group that the manager failed to control. I assure you we won't return. read more

Our first time here. We were greeted by Mario and he sent us a free anti pasta appetizer which was yummy. My husband got the sea bass and it was very delicious. I got the surf and turf, the filet was great but I didn't care much for the scollops or shrimp. The desert was excellent I had the carrot cake and chocolate ganache. read more

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Delicious food great hospitality the waiters were super friendly and the owner was very attentive. Came for our anniversary and it was well worth it! read more

Food was amazing and the service was excellent. Outside dining was great. Owners stopped by the table to introduce himself and check on us.