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O'Leary's Seafood Restaurant

Certificate of Excellence
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310 Third Street, Eastport, Annapolis, MD 21403-2510 (Severn Avenue)
+1 410-263-0884
17:00 - 21:00
Closed now
See all hours
Sun 10:00 - 14:00
Sun - Thu 17:00 - 21:00
Fri - Sat 17:00 - 22:00
More Info
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289 Reviews from our TripAdvisor Community

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Time of year
Showing 288: English reviews
Basking Ridge, New Jersey
Level Contributor
37 reviews
29 restaurant reviews
common_n_restaurant_reviews_1bd8 4 helpful votes
Reviewed 1 week ago

Six of us went out for fresh seafood and a few drinks. We had a great time at O'Leary's. The food was very good - not the best in town but well worth it. Our server was great. I just wish I remember her name.

Thank Mike L
Level Contributor
4 reviews
Reviewed 2 weeks ago

I was a little worried when we called at 8 to make a 8:30 reservation, but they were fine with it and we hurried over from our BnB (Two O One) whom recommended O'Leary's. We had a long day and wanted a relaxed meal and that's exactly what we got. The tuna tartare was excellent and then my wife and... More 

Thank Trey A
Washington DC
Level Contributor
34 reviews
16 restaurant reviews
common_n_restaurant_reviews_1bd8 24 helpful votes
Reviewed 2 weeks ago

O'Leary's is a place I've been going to for about 20 years and it has always remained consistently good, even when the ownership changed a number of years ago. Excellent choices of fresh fish and a great selection of wines.

Thank Roadwarrior098
Wil P, Owner at O'Leary's Seafood Restaurant, responded to this review

Thank you for the kind words. The O'Learys tradition is a strong one and I want to make sure it stays that way. Cheers! More 

Edgewater, Maryland, United States
Level Contributor
16 reviews
13 restaurant reviews
common_n_restaurant_reviews_1bd8 4 helpful votes
Reviewed 14 March 2017 via mobile

Our previous dining experiences at one of our Annapolis favorites was not to be repeated this past Valentines Day. We had a reservation for 4 diners and were promptly seated upon arrival. After which point the experience went completely downhill due to service and facility issues. We waited over 20 minutes for the server to take our drink orders and... More 

Thank Jamie3332
1 review
Reviewed 18 February 2017 via mobile

We're locals. Frequent O'Learys. Food is top notch. Service Even Better! The lobster or Crab Cakes are tops all year round.

Thank Scot G
Dallas, Texas
Level Contributor
15 reviews
7 restaurant reviews
common_n_restaurant_reviews_1bd8 18 helpful votes
Reviewed 26 January 2017

Just what we were looking for after a long travel day, good local cuisine without a lot of background noise. We spent three nights in Annapolis on Inauguration weekend and dined at O'Leary's twice so obviously we thought it was a good value and worth a 2nd visit.

Thank N708Y
Level Contributor
48 reviews
34 restaurant reviews
common_n_restaurant_reviews_1bd8 12 helpful votes
Reviewed 22 January 2017 via mobile

This was our second visit and O'Leary's is still our favorite! Best Crab Cakes I have ever had for main course, we tried the Diver Scallops for an appetizer and it was fabulous! O'Leary's always has a great menu and you cannot go wrong with whatever you choose!

1 Thank Fcafc
Lancaster, Pennsylvania
Level Contributor
169 reviews
112 restaurant reviews
common_n_restaurant_reviews_1bd8 48 helpful votes
Reviewed 22 January 2017

It was a quiet weeknight evening in January so the restaurant was not busy at all. I can imagine that in-season this place would be quite hectic but on this night it was delightful in every sense of the word. We brought along a special bottle of wine to enjoy ($15 corkage) and the server was delighted to open it... More 

1 Thank Bob G
Level Contributor
5 reviews
common_n_restaurant_reviews_1bd8 1 helpful vote
Reviewed 19 January 2017

Was in Annapolis for a couples overnight and what a wonderful surprise to find this Gem of a Restaurant. From Start to Finish it was the best dinner. Our waitress Jessica was fantastic and very knowledgeable about the menu & drinks. Can not wait to return in the future. It will be our go to restaurant.

Thank MARY L
Venice, FL
Level Contributor
37 reviews
23 restaurant reviews
common_n_restaurant_reviews_1bd8 18 helpful votes
Reviewed 18 January 2017

O'Leary's always has very good seafood, but it is expensive. It is a small place and tends to be quite crowded and a bit noisy.

Thank John_HVenice_Fl

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Restaurant Details

Rating summary
  • Food
    4.5 of 5 bubbles
    4.5 of 5 bubbles
  • Value
    3.5 of 5 bubbles
    4 of 5 bubbles
Average prices
USD 28 - USD 37
American, Seafood, Contemporary, Vegetarian Friendly
Restaurant features
Takeout, Parking Available, Serves Alcohol, Reservations, Seating, Waitstaff, Free Off-Street Parking, Wheelchair Accessible, Full Bar, Wine and Beer, Accepts American Express, Accepts Mastercard, Accepts Visa, Accepts Discover
Dining Style
Casual Elegant
Good for
Local cuisine, Business meetings, Special Occasion Dining, Romantic
Open Hours
10:00 - 14:00
17:00 - 21:00
17:00 - 21:00
17:00 - 21:00
17:00 - 21:00
17:00 - 21:00
17:00 - 22:00
17:00 - 22:00
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: +1 410-263-0884

Questions & Answers

Here's what previous visitors have asked, with answers from representatives of O'Leary's Seafood Restaurant and other visitors
5 questions
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Annapolis, Maryland
2 months ago
Annapolis, Maryland, United States
Rippon, West Virginia
over a year ago

See all questions (5)

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?