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O'Leary's Seafood Restaurant

Certificate of Excellence
American, Seafood, Contemporary
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310 Third Street, Eastport, Annapolis, MD 21403-2510 (Severn Avenue)
5:00 pm - 10:00 pm
Closed now
All hours
Sun 10:00 am - 2:00 pm
Sun - Thu 5:00 pm - 9:00 pm
Fri - Sat 5:00 pm - 10:00 pm
More Info
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258 Reviews from our TripAdvisor Community

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Time of year
Showing 257: English reviews
Level Contributor
141 reviews
117 restaurant reviews
common_n_restaurant_reviews_1bd8 33 helpful votes
5 of 5 stars Reviewed 2 days ago NEW via mobile

Everything was outstanding. We started out with cream of crab soup and mussels. We had scallops and blue cobia florentine for our main courses and fresh berry shortcake for dessert. When we got the bill our wine was 1/2 price since it was Tuesday. Outstanding wine list and parking.

Thank GooseCowboy
Annapolis, Maryland
Level Contributor
16 reviews
10 restaurant reviews
common_n_restaurant_reviews_1bd8 8 helpful votes
5 of 5 stars Reviewed 2 days ago NEW

We go there for our wedding anniversary almost every year. 33rd this year. Rather small in size, but the menu and food is incredible. I highly recommend getting a reservation. Service is great, not super fast or rushed. In fact if anything it is slow and easy going. I had crispy rockfish (a staple there) and my wife had sopa... More 

Thank Michael K
Level Contributor
9 reviews
7 restaurant reviews
common_n_restaurant_reviews_1bd8 7 helpful votes
5 of 5 stars Reviewed 1 week ago via mobile

After a long search of seafood restaurants we ended up here the food was great the atmosphere is very intimate love this place would definitely recommend this to anyone The crispy rock fish was Great also Deep dive scallops

Thank RicoBronya
upstate pa
Level Contributor
147 reviews
117 restaurant reviews
common_n_restaurant_reviews_1bd8 39 helpful votes
5 of 5 stars Reviewed 3 weeks ago via mobile

I think O'Leary's Seafood restaurant is one of the best seafood places around. I travel quite a bit and I am shocked when I go to different towns on the Eastern seaboard including Florida that there is no restaurants that compare to this place in Eastport. My hat is off to O'Leary's for running such a great establishment for all... More 

Thank twmUpstatePa
Level Contributor
5 reviews
common_n_restaurant_reviews_1bd8 11 helpful votes
5 of 5 stars Reviewed 4 weeks ago

Every time we go to O'Leary's it's spectacular. The service and attention to detail and the quality of the food is the best that Annapolis has to offer. WE have lived here for over 20 years and there isn't a close second.

1 Thank Rob B
Ansonia, Connecticut
2 reviews
3 of 5 stars Reviewed 4 weeks ago

We were a party of six for dinner with a reservation. When we arrived we were shown to a booth, we asked if a table was available and were told no - parties of six are seated in booths. We took the booth but for six people it was quite uncomfortable. To be fair our server was good too bad... More 

Thank Sharon G
Salisbury, Maryland
Level Contributor
4 reviews
common_n_restaurant_reviews_1bd8 3 helpful votes
5 of 5 stars Reviewed 4 weeks ago

I requested 3 vegetable side dishes as I'm a vegetarian. The chef spun them together to create a lovely meal. Thank you so much!

1 Thank Kimberly R
1 review
5 of 5 stars Reviewed July 16, 2016 via mobile

Great food....fantastic service-Demetri was awesome and a great atmosphere...best food all weekend ...rockfish is amazing as are the lettuce wraps and salmon bruschetta ... Had the special black widow cod and it was delish!!! Totally coming back again!!!

Thank Michelle H
Chicago, Illinois
Level Contributor
3 reviews
4 of 5 stars Reviewed July 6, 2016

We had a good fish dinner, but the service was very mediocre for a nice restaurant. I'm allergic to dairy and asked if one of the fish dishes could be prepared without butter and was told no. I ordered another entree which came with goat cheese on it. It's sometimes difficult to get substitutions at low-end restaurants, but I expect... More 

Thank DanLondon2014
Locust Grove, Virginia
Level Contributor
6 reviews
3 restaurant reviews
common_n_restaurant_reviews_1bd8 3 helpful votes
4 of 5 stars Reviewed July 6, 2016

Our waiter was very nice and friendly. He explaned the features and preparation of the dishes and offered helpful recommendations.

Thank lousyweekend

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Restaurant Details

Rating summary
  • Food
    4.5 of 5 stars
    4 of 5 stars
  • Value
    3.5 of 5 stars
    4 of 5 stars
Average prices
$28 - $37
American, Seafood, Contemporary
Restaurant features
Takeout, Parking Available, Serves Alcohol, Reservations, Seating, Waitstaff, Free Off-Street Parking, Full Bar, Wine and Beer, Accepts American Express, Accepts Mastercard, Accepts Visa, Accepts Discover, Private Dining, Wheelchair Accessible, Free Wifi
Dining Style
Casual Elegant
Good for
Business meetings, Special occasions, Local cuisine, Romantic
Open Hours
10:00 am - 2:00 pm
5:00 pm - 9:00 pm
5:00 pm - 9:00 pm
5:00 pm - 9:00 pm
5:00 pm - 9:00 pm
5:00 pm - 9:00 pm
5:00 pm - 10:00 pm
5:00 pm - 10:00 pm
Location and Contact Information
  • Address: 310 Third Street, Eastport, Annapolis, MD 21403-2510
    (Severn Avenue)
  • Public Transportation: Water taxi
  • Location: United States  >  Maryland (MD)  >  Annapolis
  • Phone Number: 14102630884

Questions & Answers

Here's what previous visitors have asked, with answers from representatives of O'Leary's Seafood Restaurant and other visitors
1 question
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Rippon, West Virginia
over a year ago

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Questions? Get answers from O'Leary's Seafood Restaurant 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?