Is this really a gay bar? Gay-friendly, sure, but honestly, other than the rainbow symbol in their logo and a few of the provocative cocktail names (The Naked Experience, Cucumber Catcher). This is actually the in-house bar cafe for the compact Staypineapple Hotel where we were staying in Boston (review: https://yelp.to/iittq3ioql). As a hotel guest, we were entitled to complimentary glasses of wine (photo: https://yelp.to/VZfvDvRXXU). Chardonnay for Jamie, Merlot for me. They were generous pours, and it was a nice enough experience that we came back twice during our stay. Each time, we both went for the $15 A Cup of Joe, an espresso martini with vodka, kahlua, and for $2 more, Bailey's (photo: https://yelp.to/gOfz2lyTgh). That was a refreshing delight worth repeating, and the staff was quite friendly. Definitely inclusive here but if you want a more distinctively gay experience, go to Club Cafe (review: https://yelp.to/ij4qTOWnsD). COCKTAILS / WINE - 4 stars...espresso martinis are the bomb here AMBIANCE - 4 stars...open with a long bar and a lot of windows SERVICE - 4 stars...very friendly and polite TOTAL - 4 stars...inclusive but not that gay RELATED - Exploring Boston? Here's my collection of places I've visited and reviewed: https://bit.ly/3XtfnFc read more

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Fun place to grab drinks and food. Staff was welcoming and friendly. Restrooms were clean and stylish which was an added bonus. Great location in the South End and will stop by next time I'm in the area. read more

Trophy Room - Chicken caesar salad - Cocktail Bars Near Me - Boston, Massachusetts

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Work event was hosted here, very friendly staff and the patrons are also great. We all got drinks-- they make a great martini, my margarita was very good, and the pizza and hummus they brought out was surprisingly (sorry) delicious, many remarked. The ambience is nice, a cosy bar with hightop tables around large windows with cool city views. There's a stretch of the space to the left of the entrance that has lower seating, many groups were gathering while we were there. Will be back. read more

Great friendly staff, great bar. It is a bit cozy, but still with a cough space for a few groups. After enjoying a couple drinks at the bar we ordered a couple pizzas to take back upstairs to our room. The kitchen is small and fairly open so it was kind of nice to see the cooks prepare the foods and their attention to detail. Food was great, the mushroom and Brie pizza is something that we're going to have to make back at home. They do a really good job with a small space and were really good at making sure that all guests got served in a timely fashion. read more

Trophy Room - Mushroom and Brie pizza - Cocktail Bars Near Me - Boston, Massachusetts

Sub par cocktails for $20. Dont order beer because they serve it room temp. Acoustics are horrible and they have a light show that mimics an ambulance. read more

This is a cute little bar adjacent to the Staypineapple hotel in Boston. We were staying at the hotel and decided to pop in on a Thursday night and it was about 1/2 full of patrons. We ordered an Aperol Spritz, a draught beer, and the Trophy Nachos. The drinks were cold and the nachos were really, really good! They were piled high with chips, tomato salsa, onions and lots and lots of tender pork. They were topped off with sour cream and sliced avocado. We were definitely enjoying our nachos when a d.j./trivia host asked us if we wanted to play trivia. We often play back home in Florida, but there were just 2 of us. We decided we'd give it a try; and ended up winning first place which was a $25 gift certificate. We were able to apply it to our tab; so definite a win for us! I liked this place because it was away from all the hustle and bustle of downtown Boston, plus it had good food and good service as well. I would definitely check it out if you're staying at the Staypineapple Hotel or anywhere in the Back Bay Area. read more

Trophy Room - The Trophy Nachos.....truly loaded and delicious! - Cocktail Bars Near Me - Boston, Massachusetts

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Great service! Great drinks! Pizza . Vibes . Music was awesome. Garnett had amazing service! Will be back!

A neighborhood favorite! We love coming here for drinks as the bartenders are all super friendly! I've gotten food a few times, and my favorites were the burger and fish tacos. Kitchen is small and fun to watch if you're sat near it :) they also have trivia on Thursdays which can be small but fun questions that you submit using your phone! read more

Welcoming atmosphere and great drinks and service. The food was ok, it was basic bar food in selection and quality. It wasn't bad but I was hoping it was a bit more elevated. We ordered the wings as an app, I had the cubano sandwich and my date ordered the chicken sandwich. They both were a bit dry and the cubano sandwich was a mid representation to the Cuban Sandwich. The drinks however were stellar. I had the Purple Reign and my date had a Sangria we both enjoyed our drinks. read more

Great spot. Came here for a quick drink before seeing a show nearby. Ordered the Dirty Shirley (13) and I thought it was pretty decent. I liked the vibe inside, it had your typical sports TVs playing but also had some nice DJ, pop remix going on as well. Pretty busy overall but drinks and vibe was good. Would recommend! read more

Trophy Room - Dirty Shirley (13) - Cocktail Bars Near Me - Boston, Massachusetts

Glass in the drinks Manager said it was plastic and we're very rude. Do not go. Go to club cafe read more

Trophy Room - There was glass in the beer and the managers said it was plastic and were very rude - Cocktail Bars Near Me - Boston, Massachusetts

Stopped in to watch NFL football. Asked bartender to put on the bengals game as they had the same game on both tvs. Proceeded to tell me they were putting on tennis at 4pm. The current time was 1:30. Told him I didn't understand why they would do that since this is opening Sunday for NFL. Told me he didn't want any attitude at 4pm when tennis was to be on. I said you already informed me of that. He did not like my attitude and told me to leave after I had my beer. There were only two other people in the bar. ‍‍‍ read more

Nice place for hanging out with friends m, cocktails are ok, there's trivia night as well. Service is friendly and low key read more

Trophy Room - a person crossing a city street - Cocktail Bars Near Me - Boston, Massachusetts

Very nice urban feel and interesting people. Wonderful location and very LGBTQ friendly. Excellent drinks and super friendly staff

I visit the staypineapple when I come to town from Florida and almost always eat here at least once during my visits to Boston. I came down for lunch before leaving for the day and it was slow. I was one of the only people there and the management was talking with the staff about the flow of the day to a new employee. I ordered lunch and the service was quick. The food was very good. I had a cheeseburger and fries and a soda. I started talking with the bartender Seth and the manager was going over customer comments for the week. He jokingly said to his staff I know who these are about without the name. Seth and I chatted for a while and he had a quick wit and a sarcastic sense of humor. Definitely a Bostonian. I can appreciate the personality that maybe some visitors can't. I will definitely be back here the next time I am in town. When I came back to the hotel for the night, the bar was full and everyone looked like they were having a good time. Unfortunately I was tired from the day and retired to my room. Definitely recommend the hotel and the restaurant. read more

I've been coming here since the old days, and during transition to now - for me this place will always be great because location location location + a strong drink! The only reason I gave 4 stars is lighting is too bright at times for this place & they haven't seemed to pick a lane? Is it a restaurant or a lounge, is it a sports bar or is it a rager or maybe it just depends on the night? Either way it would be awesome if their marketing team worked on this idea. I still come here weekly so I love this place but as a customer would be awesome to put a finger on the vibe? read more

Went in on a Sunday at 745pm and ordered a martini. 15 mins later... they close the bar! Wish the bartender told me they close in 15 mins. Who guzzes a martini in 15 mins?!!! Never again! read more

I used to love this place. I don't know what happened. The manager, servers and bartenders used to be amazing. They were outgoing, friendly, funny, inviting, and quick with a smile. I haven't been to The Trophy Room in about 6 months, and when I came back they're gone. The ppl they have working there now are dreadful. Not friendly. Not inviting. Not fast, or good at their jobs. The little bartender with the glasses is rude af. If you don't like your job, get a new one. What a difference a year makes. read more

Slow service. Guy only bar. Would be nice to have this place to chill at while staying at the hotel but local hangout it seems.

Weird. This is a bar, with great potential to be a simple restaurant. They fail miserably. The food is quite good, but it does not act like a restaurant. read more

This bar isn't what it use to be. Earlier this year they brought in a new manager who drove all the loyal bartenders, who had been working there for years, to all walk out in the same night and not charge people over hundreds in bar sales. After those bartenders warned the gay community about the restructure not being gay friendly, I continued my patronage with an open mind. I could tell this guy's head was full of bricks and he seemed like the most "homophobic gay man" I've ever met. Last night before I even ordered a drink, I was showing people an approved flyer for an approved party, that the OWNER had reviewed. This manager grabbed me, pulled me, and yelled at me to stay in a corner. Is that professional for a staff member to put their hands on an individual? Like their bar sales, this place is declining and I am able to make that judgement call since I've gone almost every weekend for the last 3 years and I have bank statements to prove it. The owner of this establishment needs to remediate his decision on who he hired to oversee the day to day operations of this place. read more

We stayed in the adjoining Chandler Inn Hotel and loved seeing this cute place in the lobby. We were extra thrilled when we realized the crowd is mostly gay folks. Our first day there, a Friday, we ate dinner at 7p, right before the place starts transforming from mostly a restaurant to a Sports Bar and then almost a nightclub. Dinner was awesome. I had a special which was Ricotta Tomato Basil Gnocchi and my husband had a NY Strip Steak. I would not call this bar/pub food. It was wonderful as were the 2 cocktails I had off their custom cocktail menu. Our server Vanessa was a out of a movie. Sweet, patient, kind, attentive, million dollar smile. A second server who helped us change tables twice. --because of wobbly table legs-- could not have been more gracious about it. As we ate and the night went on, the music got more dancy, and the crowd filled in and folks were having fun. They have a more quiet seating area removed from the main bar, but we requested being at a table in the middle of the action! We ended up eating early brunch there the next morning (the selections were inventive and the food was so good) then a quick bite (flat bread pizza) at around 1p as we hurried out to an event. Both times, the service was top-notch, warm and friendly. We got back from our event at 11:30p, hungry and tired. The hotel desk clerk told us the Trophy Room had table service till midnight so we went in and waited for about 5 minutes to be acknowledged. The waiter rudely told us that he "was closing out" and that we should order at the bar. Though the place was hopping, the quiet seating area still had empty tables, but the bar had people 4 rows deep. We looked at the bar, looked back at him and he could see our expressions and shoved menus at us and repeated, go over to the bar and order real fast. His attitude, words, tone and body language were unbelievably rude by any reasonable person's observation -- and he had absolutely no self-awareness of how he was coming off. So we left and ate elsewhere. The next day, we did brunch their again because he wasn't working. Service was again so friendly and welcoming like they knew you for years or something. That night we went in just to see if he was working and saw him ingoring other customers while playing with his phone leaning over the hostess stand. So 4 stars, tempted to give 3. Without Rudy McRudington, would have been 5. Hoping the management talks to this guy and sets him straight. read more

Trophy Room - The Boatslip cocktail. Yummo. - Cocktail Bars Near Me - Boston, Massachusetts

Bartender was lovely and kind. Wife was a bit inebriated so I tried to help her in the bathroom and was promptly kicked out by the manager. I assume because people have sex in the bathroom? Saw many other couples go in together. Won't be returning. read more

Used to love this place! Sasha is one of the only people there from the old crew. The service has gone down and they got rid of the best pizza on the menu, the mushroom and Brie. I'm willing to change this review to 5 stars if they bring the pizza back. The pesto and mushroom was so oily and wet with the veggies Update 1/23 pizza is back to brie and mushroom! Service has also gotten much better!! read more

This is a beautimous place to eat and socialize. The drinks were ample and tasty and the food was delicious. Our server Frank was very good - efficient and personable. read more

I love this place! The bartenders couldn't be nicer! The drinks were very good and came quickly. It's nice to have a good ol gay bar in the old neighborhood. The customers were nice and it was an overall great vibe - music wasn't too loud either. Thank you guys for keeping it real! read more

I have only been here several times. Definitely a good go to spot to pregame before you party the night away. One of my go to drinks there is the Trophy wife but sub tequila.. muah! Food is pretty good read more

Good selection of signature cocktails at the bar; would recommend The Naked Experience. Bartender Will Hartzell was also very personable and took good care of us! read more

My friend has a couple of shards of glass in his beer and the management and one of the servers was AWFUL and very unsympathetic about what happened. DO NOT GO TO THIS BAR. The management had zero things to say about what happened except a pity apology. read more

Had a blast at Glam BINGO Brunch! The brunch buffet food was delicious and just the right amount of grease to kick the hangover. Great drink specials and the loveliest host ever. He was working in a fully packed house and was constantly making rounds to help support the wait staff. Can't wait to turn up again next month with the queens and DJ Ian Diver. Update: Trophy Room's new Executive Chef is incredible. Recommended items: breakfast skillet, frittatas, steak frites, baked chicken entree, any and ALL of the appetizers, and everything on the dessert menu. read more

Trophy Room - Tarts for dessert - Cocktail Bars Near Me - Boston, Massachusetts

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Okay so this place is a great place to grab drinks but the food is very mediocre. We went on the drag queen night and we honestly had a blast. My husband and I enjoyed watching the drag queen show and enjoyed hanging out with the people there. First time I was ever in a bar where no man was checking me out! Haha, my husband was quite the star however :) All in all, we had a great time as this place is right next to the hotel we were staying at. Highly recommend the drinks but would suggest avoiding the food. Also, they didn't have dessert which was a bummer as both of us were craving a sweet that night. The service was good and everyone was having a great time. I took away two stars as the food was so poor. Would we go back? Sure, as the ambiance and people there were fun. read more

Trophy Room - Cocktail Bars Near Me - Boston, Massachusetts

What a tremendous addition to the neighborhood! The atmosphere and attention to detail (sexy cloth napkins, pristine bathrooms), the food and drinks, pretty much everything about this place draws you in and keeps you happy. Right on the corner of Berkeley and Chandler, you can't miss it with it's wide open red doors and giant windows. I would be here constantly in nice weather (well, and in crappy weather, too, let's be honest) if I still lived in Boston! (Sniff!) It was pretty packed on a Monday night around 7:30pm or so--and I was one of about 3 ladies in the place for most of the evening, which is fine by me! It may be a beautiful restaurant/bar that tends to draw all the pretty young lads, but it's very welcoming of all. We ended up sitting in front of the chef's area (Chef Evan, who is simply charming), and asked him what he enjoyed preparing or recommended for first timers. He spoke with effusive gusto about pretty much most of the items--it was apparent that he loves both what he does and also where he works. We had the spicy cauliflower "wings" (definitely worth a try, unusual and yummy) and the kale and prosciutto saute (also nom) to start. My bf ordered the Caribbean chopped salad, which he really enjoyed, and I went the complete opposite direction and got the Trophy Burger. Seriously--go look at the photos of that bad boy. It's a BBQ burger with spicy queso and fried onion ring(s) on a pretzel roll. Do not let its daunting height intimidate you--it's far more manageable than it seems if you eat one of the onion rings separately. ;) It is a beast and it is delicious. Josh waited on us and he was fantastic--fun to joke with and very accommodating as well. After dinner, friends joined us for drinks and he let us move to an actual table to make things easier. After our friends left, we made it up the bar (which had open seats finally!) for some specialized cocktails from Will. Will is pretty much my absolute favorite bartender in Boston, and has never led me astray. Be adventurous with your cocktail choices here, it pays off quite well! Needless to say, I was one fat, happy panda by the time I left. This place is obviously going on the must-do list for future return visits. read more

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This review is for the restaurant, which is unfortunately below average, especially for the prices they charge. I would put the food on the level of your average sports bar. The highlights of our meal were the Meatballs as well as the Caprese Salad but that's not to say that they were something to come here for. They were mostly just edible. The absolute worst were the Cauliwings and the House Salad. The lettuce seemed unwashed and the croutons were stale. No idea where to even start with the Cauliwings (three cauliflower pieces). The only reason this place gets a second star is because the service was overall positive and the staff were very friendly. I wonder if perhaps it is a much better bar than it is a restaurant because the ambience was nice inside. Another annoyance, it was way too cold inside - maybe if we had a few drinks it would have warmed up but as a group of non-drinkers we were shivering. If you're considering it for dinner don't be fooled by the 4 star average review here as we were. Move on. If you're going for drinks/happy hour then go right ahead but just don't expect much from the snacks. read more

Spent last weekend at the adjacent Staypineapple with friends. Had an amazing time on Saturday night and then on Sunday afternoon for the Pats game with Frank the bartender at the Trophy Room. He was so knowledgeable and friendly, his drinks were top notch, and he took great care of the 6 of us in our group. Shoutout to John as well!! Food was great and all of the staff members were awesome. We will definitely be back! read more

Our first night in Boston and I desperately needed a salad. This was a two minute walk from where we were staying so we hit it. Seems to be more of a bar scene but our food was good. I ordered the salad I was craving and was decent. Girlfriend ordered chicken strips and they looked a little dry but she said they were good. Service was quick and friendly. A good basic sports bar type location. read more

So in recently developments in the world...the first thing I watch is the bartender in his jameson beenie decide to be chewing on his nails.....toucj my glasses for water and never once washing his hands. Disgusting. This should be addressed. Time 9:15pm. I will be in touch with management in the morning. Nasty read more

Nom! Your comfort food just got refreshed. Went classic and ordered the burger and fries. Too. Freaking. Good. The meat was perfectly cooked, the bread perfectly toasted, and those fries. Those fries! Also ordered the asparagus appetizer and was so happy to have tried it! The sauce that was glazed over it was just right - not too salty, has a hint of peanut flavors. The ambiance is comforting, good place for anyone (family, friends, couples, whatever). Gotta love it when you get to enjoy your favorite comfort food, and it comes out better than what you'd expect. read more

Trophy Room - Grilled asparagus with a peanutty sauce. - Cocktail Bars Near Me - Boston, Massachusetts

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The staff needs to stop hounding customers 30min before last call to leave. The staff was literally counting us down you have 40m, you have 30m, you have 15m, you need to leave (when they don't close for another 10m) read more

So I went to Trophy Room one night, and the bar tender made me a drink. She happened to make excess and I asked if it was possible to have the rest of what she made me. The answer was no, which is perfectly fine. I go to the bathroom, and as I'm finishing, I get a knock on the door. It's the manager and the bouncer, accusing me of asking for free drinks. Then when I want to know more about the problem, I'm all of a sudden no longer allowed to enter. Yeah. May they go completely bankrupt. read more

This is a cool venue..just not for brunch. Ultimately i came here for brunch and felt the menu was limited... it definitely looks like a cool place for drinks, later on in the evening. They have tables with couches and a bar and many high tops. The customer service was nice- one of them was training. My water glass did run empty so that was unfortunate. I got the regular breakfast $9 for 2 eggs, 2 sausages and home fries. It was very yummy but steep for that amount. Their lattes are very strong... if you prefer strong ones, this is the place to go! I also went one night for my friends goodbye- it's a great place to gather and their apps were yummy; kinda pricey..but whatever. read more