O’Connor’s Pub

I was here earlier this summer. I don’t typically go to restaurants that serve Irish/​English type food, but it’s in Chestertown, and it was later on a Saturday night– the sign said PUB. Being that it was a pub, I was hoping there was some action going on. Sadly, no action. Just a few people and families sitting around eating.
They do have these «buckets» that you can order. They have mixed drinks. I got some kind of blueberry lemonade. It was really good. I ordered shepherd’s pie and the person I was with ordered the fish and chips. The shepherd’s pie was OK… I was expecting it to be a little more seasoned. I don’t like fish, but I did try some of the fish on the other plate… liberally doused with malt vinegar. It was pretty tasty and crispy. I would have preferred it over my own dish!
The waitress/​bartender at the bar was super cool and gave us some advice on some places we might find to hang out when we left. I would probably come here again if there was something going on. It was just a little too quiet when I was there.

Went around 11:30 on a Friday morning, found it to be quiet. Sat at the bar and had great service from the bartender behind it. Philly cheesesteak sandwich was ok, somewhat unremarkable. Had one beer on tap, which tasted fresh. Not a bad place to eat, but I was most impressed with the friendly service.

Not my favorite bar in Chestertown. It gets too crowded on weekends and tries too hard to be cool. I don’t see how DJ’s and live music fit into this place. On some days they have beer pong. You can play pong in your dorm room if you really want to, so why the hell would you go for a bar to do that?
The food is better, though. I personally like the wings (all you can eat on Wednesdays) and the loaded fries.
To me, this place feels too much like a fake «Irish» joint, which is weird, because the affable owner is actually Irish. I can’t help but think it’s a little gaudy.

This little pub serves authentic Irish cuisine. Including Guinness shipped in from the homeland.
It is bar food, but a constant favorite is the crab dip. I myself love the loaded fries, some day they will make a cardiologist very happy.