Mehh. Just average. Nothing special or unique stood out to me about this place... My husband and I came here to grab dinner before catching a movie at Legacy Place. We sat at "the snug" bar hidden in a back room (sounds cooler than it was). We started with fries, which were cooked nicely to a golden brown but tasted dry as a bone! They could have used some (or a lot of) seasoning. No salt/pepper was provided and our bartender was missing most of the time so we couldn't ask for it. Thank goodness for ketchup! For my meal, I ordered the "beef & feta toastie" with a side salad. It tasted like a steak & cheese sub and a grilled cheese sandwich had a baby. And even though I like feta, swiss and arugula, the taste of the combination inside my sandwich was odd/not that great. But I'd still say the sandwich was on good quality bread that was toasted perfectly. My favorite part of my meal was the dressing that came with my side salad; I could have drank it out of a cup, it was that good! My husband had the chicken pot pie and said it was just ok. We weren't impressed with this place but I would still recommend checking it out and deciding for yourself ;) read more

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What a cozy, warm Gastropub to go to on a cold winter night in the middle of charming Dedham center! The pasta bolognese was sooo good and I liked it because it was not overbearing with tomato sauce, you could tell it was made from scratch with the tiny pieces of mirapoux carrots in it. The chic pea cake with plantains, lemon white bean spread and arugula was stunning! I should have asked if there was cumin in it but my fault. All for under 100 with drinks and an appetizer! read more

Oscar's - Chic pea cake with lemon white bean spread plantains - Bars Near Me - Dedham, Massachusetts

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Oh. My. Veggie burger!! Heaven on a Unicorn!! Yaaaassss. Omg so good!! Gather the squad and prance on over to Oscar's, thank me later... xoxox read more

Amazing drinks - shoutout to Ryan our bartender. Great music. Awesome bar section. 10/10 would come back! read more

Oscar's - Bars Near Me - Dedham, Massachusetts

I was not particularly impressed with Oscar's. Went for dinner this month (Nov 2025). The service was quite slow (took a while for our server to come take our order, they forgot a few requests we had, etc) and the food itself was not great. We ordered the snack board for an appetizer which was good, and for an entree, I had the chickpea burger which was fine but not great. My aunt had a salad with shrimp which were clearly recooked and had to be sent back to the kitchen. We did appreciate that our server comped them! Fun, casual ambiance and conveniently located in Dedham, but the food certainly didn't stand out. read more

Oscar's has the best fried pickles I've ever had -- super crunchy & crispy! I've literally ordered them at every restaurant I've been to that has them, and these are hands-down the best! read more

Oscar's - Best crunchiest crispiest fried pickles I've ever had. - Bars Near Me - Dedham, Massachusetts

The food was so bizarre. I would say I'm adventurous but that place is an example of why people stick to the basics. The steak was coffee rub or whatever it tasted like poop . I suggested the place cause I'm new to the area. It's always popping. So I thought it couldn't be THAT bad. Boy was I wrong. So embarrassing. Drinks are meh. read more

only brunch menu is served for lunch on a sunday. writing this as a reminder to self to avoid brunch here. ordered burger and parmesan fries. both were good, not the greatest but passable. only one specific critique: fries lacked salt and were a mix of limpy and crispy. waitress was occupied with larger parties involving children so i was placed on back burner for service and check ins. placed my credit card in clear view on the table, and it took over 20 minutes for anyone to come to me, to ask if i was ready for the bill. dinner service is much better. will stick with dinner hereon. note to institution: customers are all paying and do not want to feel forgotten. please, could you work on this? read more

Yummy! Really cute atmosphere and expanding into a wine bar as well . Staff is great friendly and attentive read more

Oscar's - Bars Near Me - Dedham, Massachusetts

Was really surprised to find this not a 4+ star restaurant on Yelp yet. Maybe it's all about when you go? We stopped in randomly around lunch time on a weekend when we were headed to Legacy Place for some bowling. Google Maps suggested it was a bit closer to our final destination than it was, but there was parking right out front, and we were starving, so we parked and headed in. Inside there are several tables and a bar. Next to the bar is a wood fireplace and stacks of lumber. The walls are decorated with what I believe to be South African art, which seemed to be the overall theme of the restaurant. The music when we first arrived was unfamiliar to me but mostly in the background but changed shortly after to more 90s and early/mid-2000s hits. We sat at the bar and were handed a drink menu. We saw some really nice drinks on the menu, and then noticed the very young-looking bartender (later learning was Caleb) who we weren't sure was up to the task of really mixing a good drink. We tried a number of gin drinks and a number of vodka drinks, and he hit the nail on the head of each one. They were all perfect. He checked in on each drink to make sure they weren't too sweet or if they needed anything changed. Although I didn't choose to enjoy any beer this trip, they had a decent looking selection of taps. For appetizers, we first tried the Florettes. I'm not personally a big cauliflower fan, but these were outstanding. The lemon-caper sauce will bring me back here, and the garbanzo puree was killer. Next up we tried the Hugh Piggies. The cakes themselves were delicious. I wasn't a fan of the cold Corn & Black Bean salsa that accompanied it and would skip that next time. There wasn't anything wrong with it, just wasn't for me. We were going to move on to dinner next, but the Chicken Lollipops were calling our names. They didn't disappoint. They had a perfectly crispy outside but a juicy and tender inside. They fell right off the bone, and the hoisin sauce was killer. Now becoming a little full, we decided we'd continue on the appetizer train instead of each getting a big meal. We selected the Snack Board, which comes with brie, ricotta, biltong, olives, and some crostini. A perfect end. There was a sweet syrup below the cheese as well that might become a staple of our own charcuterie boards. We ended the night deciding to relax at Oscar's instead of continuing on to Legacy Place for bowling. We ordered a few more cocktails, relaxed, and enjoyed the fire. read more

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Casual spot with delicious food and friendly service. It's gets very busy in the evenings and weekends. Call ahead to check if you have a large party. If you've never tried fried pickles - here's your chance! Yum! read more

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Bartenders was great friendly and very attentive. The place was clean drinks was on point. I ordered Dr Oscar and it was delicious so far been there 3 times and I will be going again, great place to grab a drink read more

Oscar's for lunch. Two of the classic Oscar burgers. One with reg fries and one with sweet potato fries. Let's start from the beginning. Clean little place. Excellent service. Greeted quickly, water brought and order taken. Easy to get into but very small. I can see it getting super crowded. Food orders were brought out hot and fresh. Orders were correct. Fries were hand cut, but they didn't have ranch for my sweet potato fries. If I had known that I probably wouldn't have ordered them. The burgers weren't fabulous as far as taste but they were hot and clearly just made. Decent, freshly cooked meal. Nothing special to write home about. They did a lot of things right, hence the 4 stars. I would've just preferred more flavor in the burger and some ranch for my fries. Everything was a bit bland for my taste. read more

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Terrible Caesar salad Small bowl Bunch of iceberg lettuce and a few croutons Really sad WAY over priced This was the last chance for this restaurant Lousy menu Really over priced Never again read more

Went here for a date night and really enjoyed everything! Perfectly cooked medium rare steak as requested. Took half home as it was a healthy portion. Nice ambiance. they checked our food allergy when requested. Zero complaints. read more

Oscar's - Carne asada and Fish and Chips - Bars Near Me - Dedham, Massachusetts

Cozy little gastro pub. Inventive and yummy cocktails. We opted for the small plates I stead of a big meal, but the curry smelled divine, and I'm coming back for that. Best fried pickles I've ever had for the crunch, and the Brussels were sweet, spicy, savory. The tacos are fried, so they need fork and knife instead of hands but they are super yummy. Loved the samosas. Go here. You'll love it. read more

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Food and drinks were amazing and the place is a total vibe. Will absolutely be back and are really happy we found it on a random Wednesday night. read more

Oscar's - Lavender Bee's Knews cocktail - delicious! - Bars Near Me - Dedham, Massachusetts

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This place is a chameleon. Sometimes, it's really good, the service is great, and the vibes are excellent. Other days, the food borders on inedible and the staff ignores you. If it was consistently at its best, it'd be 4-5 stars. read more

It's a really cute place. I wouldn't come here for the food. Cute place to meet up for drinks. The food is super expensive and not worth the price. It would be if it tasted good but everything just tasted bland I think they need to put more effort into it for the price. The cheese board -- they need the stop offering it. It was literally the cheapest cheeses, stale bread and lunch meats! Salami, ham-- it was so gross for the price of $18. I don't mind paying a little more for a nice meal out but it has to be really good not mediocre. read more

Food was mediocre. Service was poor and inattentive. Place has a nice feel but is lacking in every other way.

What a wonderful experience! The food and service were both outstanding. Nick, our server was very attentive, but did not hover. Food was hot and delicious. Drinks were a generous pour and good value. The owner, Michael, stopped by to make sure everything was good. Friendly and accommodating, he made us feel very much welcomed. Be sure to get his mother's recipe Brandee for desert. I and all in our party look forward to returning again soon! read more

Delicious! Great service! We will definitely come back again! Creative drink options! read more

Amazing little Irish place with American flare. The service is awesome; Juliet was super friendly and helpful, and her cocktail suggestions are the best. She made me her own special creation of a Mescal Old Fashion that knocked it out of the park! The Andiamo Tequila Spritz was equally wonderful. We also had the yuca & sweet potato fries for an appetizer, then we had the mussels in wine sauce, the fried fish tacos, and the Oscar burger. They were all wonderfully delicious. I definitely recommend this place. read more

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Maybe I'm a glutton for punishment, but I went back and it was terrible. Food sucks and the service is terrible. I have food poisoning and I'm being taken to the hospital. Something tells me I won't be going back again. read more

Always good beers, always good staff, great atmosphere, love fire place with real wood, vegan and vegetarian options that are actually good food. Couldn't ask for anything better. 10 OUT OF 10! read more

Huge mussels Good enough martini- I like them large Hummus good Sangria, good Meat and cheese very good Service very good It was on a Sunday read more

Went to Oscar's after seeing them featured on Phantom Gourmet that day. The experience was a mixed bag. First the good. The waitress was extremely nice and attentive. No issues there. As well, the restaurant has a comfortable, pleasant vibe. Now the not so good. The food was mostly disappointing, at least based on what we saw on TV. We went there expecting hand cut fries, fall off the bone short ribs, and a relatively tall banoffee pie covered generously in fresh whipped cream. My wife's fried fish was quite good, but the fries appeared to be ordinary frozen fries, the short rib was tough and a much smaller portion, and the banoffee pie was tiny with a small dollop of whipped cream. Everything tasted OK, but overall not very impressive. The food warrants a 3.5, but given the somewhat higher prices I can only give Oscar's a 3 overall. I would also recommend they pull the Phantom piece, so that people do not expect something they're not going to get. read more

We love Oscar's for a quick drink after work or a unique meal. The place is always busy (in a good way!) and the servers are always great and attentive. Only downside is that it's a bit pricey. read more

My favorite restaurant in Dedham. Great menu, love the drinks, and the interior is awesome as well. Love the new expansion and back bar! Highly recommend the poutine, it's a family favorite! read more

Ate at Oscar's a few weeks ago. Got there before the crowd, around 4:45 and was one of four tables with diners. The mixed drink before the meal was very good. We both ordered the Fettuccine Bolognese and it came out without bread, oil, ground pepper, or an offer of grated cheese. Just a medium sized dish of slightly under-cooked pasta. The bolognese sauce was tasty as was the pasta even though it was little undercooked. When the waitress stopped by I asked for some bread and it seemed that I'm the only one who likes bread with their italian meal. All in all a little disappointed and hungry so we ordered a small pizza from Dedham House of Pizza. read more

Oscar's - two plates of pasta and a fork - Bars Near Me - Dedham, Massachusetts

Food was mediocre and overpriced. Service? meh not attentive. Ambiance: loud, dark, clean. Food: The fettuccine Alfredo was tasty but dry. It was only a small portion served in a bowl and nothing else came with it for $21 - not worth the price. The fish and chips: battered fish was good, the tartar sauce was bland and soupy, the "chips" were soggy and tasted like from frozen, the tiny cup of coleslaw had gone bad - and mentioned that to the server. This was our first visit and probably our last. Overall disappointing, unsatisfying and expensive. read more

I've had many great meals at Oscar's in the past, but last night's visit was a big disappointment. While the ambiance and service remain excellent, the food was substandard. My wedge salad could be best be described as "sad," with brown and wilted lettuce and my husband's macaroni and cheese was no better than Kraft. I wonder if there is a new chef, because the food here used to be quite good. I hope this was an aberration, but fear that it's not based on other recent reviews read more

Oscar's is a cozy restaurant/pub in Dedham Square and after our first visit here we are happy to report future visits are in store. Be sure to call for day-of reservations to ensure a table as it can fill up quickly. Oscar's has a small but dynamite menu with a few small plates to start or share and a handful of entree dishes available. If you are a craft beer aficionado, all of the beers on tap come from within Massachusetts and the rotating tap options feature some really great offerings. We started with a white bean dip as an appetizer which was packed with garlicky flavor and was served with carrots, celery and crossitini. I had The Year of Dr. Nandi IPA from Aeronaut Brewing while the Mrs. had the Jolly Pumpkin from Weary Traveler. For entrees, Mrs. had the Oscar's salad which featured heirloom tomatoes, grilled ricotta, pea shoots, hand pulled croutons and was served with a shrimp skewer on top. Ridiculously good! Salad was paired with a pilsner from Medusa Brewing. For me, I went with the burger which came served with housemade pickles, lettuce, cheddar cheese and a bacon aioli. You could put the bacon aioli on a penny loafer and it would have been good! The burger was served with fries and was paired with the 413 Belgian Farmhouse from Big Elm Brewing. Other options on the menu such as the fish and chips and mussel frites passed by and looked equally amazing! Options for next time (and plenty of good beer pairings, too!) Prices were moderate but worth every penny for the quality! Highly recommend! read more

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This place is still rockin' it! The outdoor summer seating is a paradise. Head down to historic Dedham Square and enjoy!

Phenomenal! The roast chicken dish was superb! Our server (Forget his name, Red hair/Beard) was excellent! Knew the menu very well, great personality and attentive. Only suggestion I would make to the owner- 1)Remove the half wall from bar to dining area and have live music in the back left corner. 2)pendant lights over the tables should be dimmed to 25%, too much overhead down lighting while eating. Install wall sconces on back left wall to compensate for overall room lighting. Other than that, this is an awesome place with great food. read more

A limited lunch menu. Had the BLT which was perfect. Came with a nice little side of Caesar's salad. Great revolving beer menu. Lunch was slow and but service was great. The bartender was attentive. One would expect stellar service when it's slow but I've found that often it's the exact opposite at other places. Servers get bored and play grab ass and doodle on their phones. But not here. I would definitely come back here. They are expanding next door so expect so exciting changes! read more

I always bring friends here when they want to meet up in Dedham, it's a great local spot, great vibes, and a cool new space called the Snug tucked behind the bar. read more

I'm disappointed because i heard really great things about this place. I called earlier this evening to see what time they were closing and stopped serving food, the website says 12am. The woman who answered the phone confirmed they were open, allowed me to make a reservation for two. However, when i arrived and walked in the door at 8:30pm, they said the kitchen was closed, they were no longer serving and wouldn't allow me to be seated. To top it off there was a party of six outside, two groups of two at the bar, another set of four people in front of the fire, and a couple seated. The woman at the front door claimed the manager closed the kitchen for the night and blamed it on COVID. Although i understand some circumstances i drove all the way there, excepting a nice dinner and felt rejected. read more

Oscar's - My call to the restaurant earlier in the evening, making a reservation. - Bars Near Me - Dedham, Massachusetts

Incredible place. Amazing vibe and atmosphere. Shoutout to Fani our amazing bartender , we will definitely be back.

We love to come here for a bite and sit at the bar. Food is always very very good. The atmosphere is terrific and cozy. A real fire! Bartender is always pretty cool too. And they have GREAT taste in music. If you haven't gone, than you should. read more