My year at Cask.
When I graduated from college with my creative writing bachelor’s degree, I was unable to find an available job in my field, so about four months after I graduated, I started working at [REDACTED™] in Harvard Square as a host and then later as a food runner. I had a lot of issues with the place and quit after a year. At that point I’d moved into the city, and, wanting to work closer to my apartment, plus hoping to actually be a server and make real tips, I got hired at Cask ‘n Flagon, one of the mainstay Fenway sports bars on Landsdowne. The side entrances, which are fairly close to the main entrance, immediately face Gate E. Fenway Park is, I kid you not, a stone’s throw away.
It should be said that Cask’s notoriety has dwindled significantly since its glory days. The restaurant’s been around since 1969 when it was initially just Oliver’s, but Oliver’s merged with Cask and is now the “club” section of the restaurant. The place has seen a lot of different setups and crowds, and has been through many, many, many managers. Cask is no longer the de facto “go-to” spot when visiting Fenway or Fenway Park, and is mostly just a place of convenience for fans and tourists. Nobody actively seeks the restaurant out or even thinks it’s famous at this point, and it’s definitely no longer the “top baseball bar”, as the outdated cover photo suggests. I certainly wasn’t joining the staff for the clout, as there is now very little.
I started out as a host for my first month, in September of 2023, and I was dismayed to find out that almost nobody who worked with me cared about baseball, and the few people that did weren’t Red Sox fans. There were some die-hard basketball fans, avid soccer fans, and a few football fans, but I often had to explain or clarify aspects of whatever Sox game was happening that day. I’ve lost count on how many times I had to tell my coworkers how extra-innings worked, or if the Sox were good or bad at any given time. There are also several vintage photographs of old players around the restaurant, and I’d often have to tell coworkers and guests who was in them.
Photo by Nathan Klima for The Boston Globe via Getty Images
Things got more interesting once I finally got to be a server and interact with guests more directly. Most of them were families or friend-groups that were just spending the day at the ballpark and didn’t care about how close the team was to .500 or how likely a postseason push was. I’d compliment people’s jerseys and banter with visitors about the day’s opposing team.
Business slowed down once the season ended, and no bona-fide die-hard Sox fans would be there for any reason unless it was immediately before or after a game. Halloween that year got pretty hectic, but New Year’s Eve was the craziest; no guest was over 35, the servers only made tips if people bought a table (which very few people did), and the managers severely overestimated how much champagne we needed, so we poured about a thousand plastic cups of the stuff when there was half that many people in the building. You can imagine the humungous mess we had to clean up afterward.
“Dead season”, in the industry, is usually the period between January-March when nothing’s going on and it’s too cold for anyone to want to go out. The end of March, however, marked the beginning of a new season. On home-opener day, we all showed up at least three hours before the restaurant opened. I passed Triston Casas on my way over, and he was wearing a big white parka despite the fact that it was in the low 50s. I wished him good luck and he said thank you. Casas is my favorite player, so I was thrilled to walk by him.
Photo by Ted Fitzgerald/MediaNews Group/Boston Herald via Getty Images
As the season went on, I watched with dismay at our horrendous defense, but I also realized I could watch the players leave the park if I got off shortly after a game ended, so I’d stop by the player’s entrance and try to catch a glimpse. I got Duran to sign my hat (which I’d stolen from Cask after someone left it and didn’t return to to claim it, it’s a kid’s hat) and I got a photo with Brennan Bernardino. I saw Casas give a passerby a fistbump-snail. One day Papi visited Newdia, the cannabis store next door, but I missed him by about five minutes.
The season got more fun once summer hit and I had some memorable interactions with guests. I got to meet two of the Last Dive Bar guys, who were pleased that I knew about and supported their cause. A guy visiting from Ontario in his 50s tried to ask me out. A couple wrote down that Jesus loved me on the end of their receipt. I met some of the Fenway workers, who were absolutely lovely and even helped me get better seats at a game a few weeks later. Besides all that, Keith Foulke is a regular Cask visitor during the season, but he was never my customer. I also saw Sam Kennedy walk by the restaurant while he was on a phone call. I was dumbfounded and managed to wave at him, and he waved back.
Photo by Yoon S. Byun/The Boston Globe via Getty Images
My coworkers were also pretty amazing, and some of them ended up becoming my best friends and remain my best friends to this day. One is a musician with a song that got more than a hundred thousand streams on Spotify. Another had been in the military and at Yale. One has an “S” Shrek ass tattoo. Unlike at my previous restaurant, my Cask coworkers almost always made me feel included and part of the camaraderie, which I was very grateful for.
But alas, management and ownership were annoying, as they tend to be at nearly every restaurant. The food was nearly always good, (shoutout Cesar, the head cook) and I do still recommend the place as a great pre-and-postgame spot, but I determined that better work was out there for me, plus nearly everyone was leaving as the season was winding down. I left too, and somehow ended up at a worse place, which is a story for another day—although I did meet Tanner Houck and his wife at the new place, when they came to pick up takeout together.
A few other things that happened while I was there:
- During games, when the restaurant would almost completely empty out, all the servers and some of the bar staff would go to the back “club room” to eat and unwind. If we still had any tables, it was easy to serve them but still take your break. It was honestly the biggest privilege of working there, having all that space and all that time in between meal rushes. I had many an enlightening convo back there.
- We had security, who would check everybody’s IDs and make sure any belligerent outsiders didn’t cause trouble. I saw my fair share of drunk fights and arguments, along with some sophomoric behavior. One of these drunk fights involved a general manager getting punched in the face. (He no longer works there, so don’t ask for him.)
- I was working at Cask the night the Celtics won Banner 18. I was also working the night of Game 4, where everyone thought they were gonna sweep, and the crowd was a bunch of rowdy teens and college kids. I was nervous about how chaotic it was gonna get for Game 5, but the crowd was older that day, and they got sentimental instead. There were lots of hugs and a decent amount of tears, and, fortunately, no big mess to clean up. I was unable to attend the parade, as I worked on parade day too.
- I completely wore out my work shoes, which were all-black Converse high tops. Very comfortable, but not non-slip, although I only fully-slipped once. The soles got so worn that they were curving. Service industry work is not for the weak.
- Cask mostly plays the same songs on repeat. Some of them start to drive you insane after you’ve heard them for the eighteenth shift in a row, but some of them are very, very good. A personal favorite that I discovered from the Cask aux is “Jackie Down The Line” by Fontaines D.C.
- I met a Savannah Banana after their game last summer, when he and several of his (non-banana) friends came in and sat in my section. I unfortunately forget who it was.
- A fraternity had a pig-roast in the club. They were supposed to sing a ceremonial pig-roasting song but they didn’t. Cesar put an apple in the suckling pig’s mouth and gave it sunglasses.
Cask was only a year of my life, but it was an incredibly formative one with all the connections I made, be it quick encounters with Sox players or bonding with the people I consider to be my best friends now. My memories there, aside from the occasional bad day, have been mostly positive. It’s definitely worth a visit, but maybe not worth the work.
The last thing I’ll say is: if you visit, get the nachos! They’re absolutely loaded on a huge plate and they’re delicious, so they make for a great group appetizer or even a meal. I miss them, so please order some for me if you ever go.