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O'Connor's Pub

$$ - $$$
American, Bar, Pub, Irish
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844 High St, Chestertown, MD 21620-1135
+1 410-810-3338
11:30 - 02:00
Open now
See all hours
Sun 12:00 - 00:00
Wed - Fri 11:30 - 02:00
Sat 11:30 - 01:00
More Info
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53 Reviews from our TripAdvisor Community

Traveller rating
Traveller type
Time of year
Showing 53: English reviews
Baltimore, Maryland
Level Contributor
271 reviews
174 restaurant reviews
common_n_restaurant_reviews_1bd8 85 helpful votes
3 of 5 bubbles Reviewed 3 January 2017 via mobile

This place has seen better days! Needs a serious remodel. My hubby and I had drinks, which were very good . Very friendly bartender and owner.

Thank LovetheBeach821
Worton, Maryland
1 review
1 of 5 bubbles Reviewed 13 November 2016

We have been frequenting O'Connor's Pub for many years, it was an old standard for dinner when Chestertown did not have much to offer. You could always get a properly poured pint, a fish and chips, bangers and mash, and smoked fish and chips as well. Now, on a Saturday night the place was over run by at least six... More 

Thank jwkuhl
Newark, Delaware
Level Contributor
23 reviews
10 restaurant reviews
common_n_restaurant_reviews_1bd8 7 helpful votes
4 of 5 bubbles Reviewed 28 September 2016

Fun little place to stop in for a beer and authentic Irish grubs. Typical neighborhood bar decor. Nice outdoor courtyard. Friendly staff and customers.

Thank Robin T
Level Contributor
9 reviews
8 restaurant reviews
common_n_restaurant_reviews_1bd8 1 helpful vote
2 of 5 bubbles Reviewed 20 September 2016

The food was, well, bland. Really bland. Which, isn't usually the case for a pub. When I order a buffalo chicken sandwich, I'm almost guaranteed at least a bit of spice. Not so for this pub. One of the menu items was loaded french fries, covered in cheese and bacon. I ordered that. Instead, I ended up with cheese and... More 

Thank Ebon K
Chestertown, Maryland
Level Contributor
18 reviews
15 restaurant reviews
common_n_restaurant_reviews_1bd8 6 helpful votes
2 of 5 bubbles Reviewed 11 September 2016 via mobile

We were here for dinner and the food was low-end bar food, re-heated then put on a plate, with no imagination or alterations to inn price flavor. The service was sub-par (the server seemed to have no clue). This is the third time we have eaten here. The first time was pretty good, second time fair and this time was... More 

Thank Leciel4me
Level Contributor
19 reviews
19 restaurant reviews
common_n_restaurant_reviews_1bd8 8 helpful votes
2 of 5 bubbles Reviewed 12 June 2016 via mobile

End of a long Saturday playing ball, needed a beer and dinner and thought this place would hit the spot. Bottomline- don't waste your time. While the beer was cold and the service was decent, the food was terrible. Ordered the Seafood Platter and a couple of burgers. They were out of the vegetables for the Seafood Platter, then they... More 

Thank smiley9999
Level Contributor
34 reviews
20 restaurant reviews
common_n_restaurant_reviews_1bd8 9 helpful votes
3 of 5 bubbles Reviewed 2 April 2016 via mobile

Nice little pub located on the outskirt of town. An Irishman's heaven. Food was ok. It was served hot. Service was good. Nice atmosphere. Might would go back if in the area.

Thank Jmoney67
Chestertown, Maryland
Level Contributor
15 reviews
8 restaurant reviews
common_n_restaurant_reviews_1bd8 5 helpful votes
5 of 5 bubbles Reviewed 16 March 2016

Best Irish food in the area, served up by an authentic Irish owner! Pub type food but really good. Great prices on drinks.

Thank Webers2-2016
1 review
3 of 5 bubbles Reviewed 3 November 2015 via mobile

I went here on a whim to try it out. It was late but there were a few people there. Ordered a "black and tan" and was served perfectly. After enjoying it a bit, I asked for a half shot of Jameson and a half shot of Bailey's. Upon figuring out I was making a car bomb I was given... More 

Thank Anthony T
Strasburg, Pennsylvania
Level Contributor
9 reviews
8 restaurant reviews
common_n_restaurant_reviews_1bd8 1 helpful vote
5 of 5 bubbles Reviewed 15 August 2015

After so many years in kent county Frank and Betty still run one of the most friendly businesses around, and the food and drinks are top of the class.

Thank Josh S

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Restaurant Details

Rating summary
  • Food
    4 of 5 bubbles
    4.5 of 5 bubbles
  • Value
    4 of 5 bubbles
    4 of 5 bubbles
Average prices
USD 6 - USD 18
American, Bar, Pub, Irish
Lunch, Dinner, After-hours
Restaurant features
Seating, Waitstaff, Serves Alcohol
Good for
Bar Scene
Open Hours
12:00 - 00:00
11:30 - 02:00
11:30 - 02:00
11:30 - 02:00
11:30 - 01:00
Location and Contact Information
  • Address: 844 High St, Chestertown, MD 21620-1135
  • Location: United States  >  Maryland (MD)  >  Chestertown
  • Phone Number: +1 410-810-3338

Questions & Answers

Questions? Get answers from O'Connor's Pub staff and past visitors.
Posting guidelines
Typical questions asked:
  • Do you have gluten-free options?
  • Is there a dress code?
  • Do you allow dogs on the outdoor patio?