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About the Business
Established in 1969. The now World Famous Cask 'n Flagon began as a small neighborhood bar known as Olivers. What was once known as the little bar on the corner of Brookline Avenue is now a landmark location for diehard Red Sox fans, college students, locals and tourists. Mention the Cask 'n Flagon anywhere, anytime to anyone and chances are they have probably been here. With its nostalgic atmosphere, outstanding staff and its commitment to the best customer service possible, the entire team at the Cask 'n Flagon is determined to provide you with a great experience no matter what your occasion may be. Please enjoy your visit and come back soon and see us again.
Ask the Community
Q:
Do you show UFC fights here?
A:
Q:
Would I be able to watch the Penn State game here on a Saturday night?
A:
I'm not sure of the answer for you but seems how the Socks aren't playing now it might be a good likelihood. They have a lot of TV's. If no one replies with an answer I'd call and ask the restaurant itself. Have fun :)
Lori F.Â5 years ago
Recommended Reviews
Overall rating
697 reviews
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Zach S.Venice, Los Angeles, CA3412Jan 27, 2015Updated reviewThanks to all for your outpouring of support for former Cask bartender Zach Azzam who was wrongfully terminated for a Yelp review that has now been REMOVED. The community spoke. The truth came out. Yelp has responded. I wonder what Cask management has to say for themselves?
EMAIL FROM YELP (to yours truly):
Hi there,
We're writing to let you know that we've evaluated Kitty K's review of Cask'n Flagon that you recently flagged. After assessing the review carefully against our Content Guidelines, we agree that this review should be removed.
We rely on community engagement to help keep Yelp useful. Thanks so much for taking the time to bring this matter to our attention!
-The Yelp Support Team
Helpful 2
Thanks 0
Love this 1
Oh no 0Jan 20, 2015Previous reviewHi, this review is for you, owners/ management, first--because you disgust me--and, second, for all you patrons considering spending any money here (HINT: do not). As a Boston resident for 29 years, a Boston University graduate, and big Red Sox fan, Cask historically has offered a fun option for drinks in the Fenway area. But as my friends and I have matured, we've struggled with the younger/ obnoxious crowd that oftentimes fills the bar--definitely around Sox games and big tentpole sporting events. We stopped going to Cask entirely 3 years ago--we literally shared a collective sigh when we were like "this isn't fun anymore" in reference to Cask--opting for nearby spots with better beer selection like Yard House. But rather than me go on about the reasons I stopped going to Cask a few years ago (there's so many), I'd like to explain why we started going back: ZACH. Yes, Zach--the bartender the impulsive management team just fired. Zach, by so many accounts, is considered one of the best bartenders to come out of Somerville/ Cambridge--he seriously has Cocktail-like skills behind the bar. That's not what makes him great, though. He's a good person. He's befriended more patrons in Boston/ Somerville/ Cambridge than I can count. I've been invited to more parties and made more friends (at and outside of Cask) due to the network of GOOD people Zach connects. He's the sort of person that makes a group of almost-30 year-olds say "screw it, we're going to Cask again because Zach is there. He's a good dude." And that's what happened. When Zach got a job at Cask, the Somerville/ Cambridge community was sad to see him go, but we were happy for him. It painted Cask in a good light for hiring him. And, most importantly, it gave us all a reason to go visit Zach in the Fenway area. In a lot of ways, Zach has been an ambassador to the city of Boston, someone I've pointed friends, clients, family to time and time again. We've sent countless people visiting Boston to Cask to "say hello to Zach.. he'll make you feel at home"--and I have countless stories about folks from around the US and the globe who have gone to Cask and been amazed at how wonderful Zach made them feel. So, having watched quietly on the sidelines while ONE PERSON (this person happens to be a female, but I call them a "person" because sex is no part of this--I just want to be clear) decided to take to Yelp to bad mouth the best bartender my large crowd of affluent Bostonians have come to love, I felt compelled to stand up for Zach and let the Yelp community know that the management of Cask has no backbone whatsoever and would simply fire an employee based on a negative Yelp review. I'm a believer in community-driven content, it's just sad to see a bar believe so much in it that they'll fire an employee over unsubstantiated words. The one negative Yelp reviewer caused management to respond: "take him off the schedule, get his shift covered." This happened immediately. Zach was given no benefit of the doubt, no opportunity to defend himself, nothing. And now Zach is out of a job. Where's the justice in that? I can honestly say I now have that one final reason why I never need to walk in Cask again. And with whatever happens to this Yelp review I write, rest assured it's being copied and pasted into my Facebook news feed as well as being sent out in a large email chain to the 100 or so friends Zach and I have connected through the better part of this past decade. Cheers.
Chris S.Sharon, MA34918Mar 22, 2024Sorry cask n' flagon...tonight was just not a great experience. We cane in for some March madness and had a good time. But it was mostly because of the friends. Drinks were good and strong. Service was good. My friend ordered a burger medium rare and it was genuinely raw inside. I thought he was exaggerating but I too took a bite and it was straight up not cooked enough.
I kept hearing about this "new pit master" and "expensive smoker" so I said what the hell, I'll try some bbq. It wasn't good. No essence of smoke, brisket sliced thin, ribs mediocre at best. Cask is a good sports bar but that may be where it endsHelpful 1Thanks 0Love this 0Oh no 0- Mar 16, 2024
Came to Cask'n Flagon for the first time with my girlfriend last night, and left feeling very satisfied! We walked in on a Friday around dinner time, and were seated right away. At first glance, it was a bit loud and crowded (as expected for a sports bar), but the waitstaff took us to a more secluded area within the restaurant (might I mention, unprompted) which was more quiet. This was appreciated!
The service was phenomenal, and all of the waitstaff was very friendly. Our food came quick (within 20 minutes) and it was MIGHTY delicious! My girlfriend and I split the Buffalo chicken wrap and grilled chicken focaccia sandwiches. We each order one entree so we could share and split them! On the side we got fries and a Caesar salad-- the salad was a substitute and we were able to order it without any extra charge!
The portions were perfect, the food was fresh, and amazing. The grilled chicken sandwich was extremely flavorful and the pesto sauce was one of the best I've ever had. The Buffalo chicken wrap was very good, but slightly messy. The fries were average and the salad was good, but I would've liked a little bit more dressing! Overall, we had a great time here, and will definitely be back!
Helpful 2Thanks 0Love this 1Oh no 0 
97931Mar 15, 2024I've been to Cask'n Flagon twice now, and I liked my first experience better than the second. This time around, I arrived with my girlfriend without a reservation around 5:20. This seemed to be before peak time, so we were seated quickly and immediately greeted by several members of the waitstaff. We got our waters and put our food order in rather quickly. They were very polite and super flexible especially when we wanted to substitute one of the sides for a side caesar salad!
However, I noticed a difference in the food. Both times, I've ordered the grilled chicken focaccia sandwich with fries. The sandwich this time around had less flaky bread, which was disappointing. Otherwise though, the sandwich was delicious! My girlfriend ordered the buffalo chicken wrap, and we split both the sandwich and the wrap. I noticed that the wrap was very messy and fell apart easily.
The fries were super fresh and crispy, and were absolutely delicious!
We were seated in a quieter area of the restaurant, away from the bar and had a great view of Boston and Fenway Park. Overall, a great experience and definitely worth a stop if you're in the Fenway area! We will be back!Helpful 1Thanks 0Love this 1Oh no 0- Oct 29, 2023
Spent many years walking by this place and finally decided to try it. Location wise, it is great. It is located right near fenway Park (parking around here can be expensive depending on when you are there. Avoid parking there during events if you don't want to pay an arm and leg). Someone in my party was already there when I arrived, so we were immediately seated. It was a beautiful day so we sat outside, which was nice. I didn't step inside the restaurant. So, I can not comment on the interior or the ambiance.
Our waiter arrived shortly after sitting and was very friendly. They were new to the job but did a good job. Someone in our party had a gluten allergy, and they took that very seriously, which was nice to see. The drinks were very tasty. The food was mediocre. I ordered a foccia grilled chicken sandwich, and I wish that the bread was warmed and the cheese/cheese spread was melted more. Also, I was the bread was more of a foccia bread rather than a fluffy roll. The sweet potato fries were tasty but I wish they arrived hot
Helpful 1Thanks 0Love this 1Oh no 0 - Sep 25, 2023
We stopped here after a Fenway Park tour because we needed to sit and have a snack. We each got a drink and shared a HUGE piece of Oreo Ice Cream Pie. It was really good and definitely large enough to share.
They have a nice outdoor seating area and the service was good.
Helpful 0Thanks 0Love this 0Oh no 0 - Sep 22, 2023
We've lived here for 16 years and only came for the first time in August. Quick late lunch after on a Friday afternoon. Not too crowded.
Fried chicken sandwich was perfection. Probably my favorite chicken sandwich ever. That says a lot!
Fenway burger was solid , juicy, not too greasy (notes from hub)
Service was great.
Music still a little loud even for lunch but oh well.
Will definitely come back and only for lunch.
Helpful 0Thanks 0Love this 0Oh no 0 
684110333Dec 5, 2023A sports bar punching a bit above its weight.
Cask'n Flagon seems like the type of place that gets packed whenever there's a Red Sox game in Fenway. It was pretty empty for a Patriots game during the horrible 2023 season and on Thanksgiving weekend, so this may not be the most representative experience.
Service was friendly. The cocktails were surprisingly decent and their menu showed that they are trying to offer both food and drinks beyond the typical sports bar fare. I appreciate that they play the sound for games (not only on the dining room, but even in the bathrooms!)
A good spot to watch the game and grab some drinks and eats.Helpful 0Thanks 0Love this 0Oh no 0- Aug 30, 2023
The Cask is a must-stop if you attending a Sox game. Get there early to secure a seat at the bar. The Cask has a good selection of local beers and a full bar. We did not eat but the folks around us were and they reported that the food was very good.
There is also a sidewalk sitting area if you are into that, we aren't.
Fans for both teams easily mingle here so feel free to wear your team gear.Helpful 5Thanks 0Love this 6Oh no 0 - Apr 29, 2023Updated review
One of the busiest sports bars in the city. Don't sleep on their food either.
Boasting an expensive smoker, top quality BBQ options and classic American cuisine options satisfy all your hunger before and during big game days!Helpful 0Thanks 1Love this 0Oh no 0Dec 20, 2022Previous reviewGotta come here for the vibe before a Red Sox game or concert! Yes it's busy and crowded but the food is solid and the experience is a must in Boston! Love it here, and will be back!
- Aug 30, 2023
Came down here for a socks game and found this place because it was not as crowded as the others. The game has already started we wanted to grab some cheaper food (than the stadium has) and drinks before heading in. We got the pulled pork which was a large portion as it also came with two sides. We got Vegas bombs which our bartender (a teacher during the school year) actually knew how to make and he made them strong! Just moving up here from Texas. This was the first place but I felt actually gave you good service.
Helpful 1Thanks 0Love this 0Oh no 0
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