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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 - 22:00
Closed now
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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273 Reviews from our TripAdvisor Community

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Time of year
Showing 272: English reviews
Silver Spring, Maryland
Level Contributor
91 reviews
52 restaurant reviews
common_n_restaurant_reviews_1bd8 55 helpful votes
5 of 5 bubbles Reviewed 2 days ago NEW

I went to O’Leary’s last night for my wife’s birthday dinner. I was keeping an open mind after reading some of the reviews , especially the one that played the race card. Upon arrival Denise the host and waitress greeted us and escorted my wife and I to our table. From that moment on we were in for a fantastic... More 

Thank DMAN0431
Kingston, New York
Level Contributor
56 reviews
45 restaurant reviews
common_n_restaurant_reviews_1bd8 32 helpful votes
5 of 5 bubbles Reviewed 3 weeks ago

O'Leary's is located in what looks like an older cottage. Inside, it's absolutely charming, with seating arranged in different rooms; cozy without being cramped. If you'd like to start with a cocktail, there is a fun and imaginative drink menu available. But the food...wow. The seafood options are so wonderfully appealing, it's hard to choose, but be assured, no matter... More 

1 Thank Susan D
Level Contributor
30 reviews
24 restaurant reviews
common_n_restaurant_reviews_1bd8 9 helpful votes
5 of 5 bubbles Reviewed 4 weeks ago via mobile

A quiet little place in Eastport that serves great seafood. Janie had the salmon and I had to test out the crab cakes. Both were superb. When i drive the water taxi, and am asked where to go I mention the obvious ones but then say my favorite is O'Learys. Just one of those secret places that most towns have... More 

Thank Pete C
2 reviews
common_n_restaurant_reviews_1bd8 1 helpful vote
4 of 5 bubbles Reviewed 2 November 2016

If you are looking for a special restaurant for a special and long dinner this is the place Service does not rush you, provides; meal was well phased. Not cheap - $50/ person..no desert and not the most expensive items on the menu [ 2 glasses house wine Menu had some uniquely prepared items.- Worth the experience for that; .Food... More 

1 Thank jimg545
Level Contributor
3 reviews
3 restaurant reviews
4 of 5 bubbles Reviewed 24 October 2016 via mobile

Excellent seafood dishes service was actually very good. We moved to a booth because the table was small for 4. Like the NYC scene, on the noisy side--booth also quieter

Thank jack l
Washington DC, District of Columbia
Level Contributor
11 reviews
common_n_restaurant_reviews_1bd8 9 helpful votes
5 of 5 bubbles Reviewed 19 October 2016

I hadn't been to O'Leary's for several years. The restaurant is under new ownership and it has a more modern, stylish vibe now. The food was excellent: the calamari, the crispy rockfish, the braised short ribs with gorgonzola to name a few. They continue to have a fun wine list with lots of choices by glass or bottle. If you're... More 

Thank nikkiwoj
Monterey, MA
Level Contributor
28 reviews
16 restaurant reviews
common_n_restaurant_reviews_1bd8 23 helpful votes
4 of 5 bubbles Reviewed 18 October 2016

It's current chef must be pretty darn good: on a very, very busy evening, everything was cooked perfectly: we had crab cakes on fried green tomatoes, the crispy rock fish, and halibut (or something similar) -- all well prepared and well cooked. Service was quite slow, but it was a very busy night and we were in no rush. A... More 

Thank PickyinMonterey
Williamsburg, Virginia, USA
Level Contributor
254 reviews
143 restaurant reviews
common_n_restaurant_reviews_1bd8 80 helpful votes
4 of 5 bubbles Reviewed 16 October 2016 via mobile

About a 15 to 20 minute walk over the bridge from the Marriott Riverside Hotel. There is a water taxi that takes about five minutes, which is conveniently located from the restaurant. Located in a former home, the restaurant has charm. The cream of crab soup with Sherry was excellent. The crabcakes over fried green tomatoes were delicious. Enjoyed a... More 

Thank Roy F
Rio Rancho, New Mexico
Level Contributor
163 reviews
115 restaurant reviews
common_n_restaurant_reviews_1bd8 36 helpful votes
4 of 5 bubbles Reviewed 13 October 2016

Not right on the water but close enough to smell and feel the bay. This was a bit fancier than our first meal in Annopolis but the prices were about the same. Interesting that a couple of their fish specials are not from the local bay. I had the Crispy Rockfish and my wife had their Bali Barrimundi fish dinner.... More 

1 Thank Kirk H
Panama City Beach, Florida
Level Contributor
28 reviews
22 restaurant reviews
common_n_restaurant_reviews_1bd8 7 helpful votes
4 of 5 bubbles Reviewed 7 October 2016 via mobile

We went there for the crab cakes and they were fantastic. Huge lumps of crabmeat cooked to perfection. Served over fried green tomatoes that were absolutely amazing. The corn side dish was delicious, too. The restaurant is located in a historic building and was decorated with a modern flair. There is no water view but they do have parking, which... More 

1 Thank Zmomz

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Restaurant Details

Rating summary
  • Food
    4.5 of 5 bubbles
    4 of 5 bubbles
  • Value
    3.5 of 5 bubbles
    4 of 5 bubbles
Average prices
US$28 - US$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, Private Dining, Free Wifi
Dining Style
Casual Elegant
Good for
Business meetings, Special Occasion Dining, Romantic, Local cuisine
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
3 questions
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Annapolis, Maryland, United States
Rippon, West Virginia
over a year ago

See all questions (3)

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?