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O'Leary's Seafood Restaurant

) #13 of 271 Restaurants in Annapolis $$$$ American, Seafood,
310 Third Street, Eastport, Annapolis, MD 21403-2510
+1 410-263-0884
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  • Excellent62%
  • Very good23%
  • Average9%
  • Poor2%
  • Terrible4%
Travellers talk about
“rockfish” (33 reviews)
“seafood” (62 reviews)
“crab cakes” (69 reviews)
Closed Now
All hours
American, Seafood, Contemporary, Gluten Free Options, Vegetarian Friendly
310 Third Street, Eastport, Annapolis, MD 21403-2510
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Reviews (302)
Traveller rating
Traveller type
Time of year

1 - 10 of 302 reviews

Reviewed 3 days ago

The best crab cakes ever. There is literally 2 bed crumbs and the rest is lump crab meat. The service is great. The special are usually amazing too!

Thank Kimberly D
Reviewed 2 weeks ago via mobile

We dined here 7 years ago when in town for a conference. It is still wonderful all these years later. We had calamari as our appetizer. The breading was more batter-like and tasty. We both had the crab cakes. Out of this world! I don't...More

Thank Nena_Skidoo
Reviewed 2 weeks ago

The restaurant has an almost hole-in-the-wall feel to it. It's located in an unassuming building on a side street. But once inside, character abounds. It's decor is charmingly seaside without being eclectic. The food options are mostly Atlantic Coast seafood options done well. The presentation...More

Thank ks_doc11
Reviewed 3 weeks ago

Our meal was delicious. We started with the calamari - delicate and crispy. For dinner we had the crispy Rockfish and Scallops - also delicious. The service was wonderful. But the best part of all was that my husband dropped his wallet at some point...More

Thank susankleinman
Reviewed 3 weeks ago via mobile

The crab cakes and crispy rockfish were fantastic. The somalier recommended a delicious crisp Pinot Grigio.

Thank elaine1862
Reviewed 3 weeks ago

Food is a bit pricey comparing with the Chart House and the Carrol's Greek in terms of size, food quality and the environment. The one who delivered dishes to the table was a bit odd. He was silent all the time. Tiramisu does not have...More

Thank Rachel-from-PLUTO
Reviewed 4 weeks ago via mobile

First things first, when using TA make sure to go to the restaurants web site rather than relying on the menu on TA. My wife and I both had something we had found on the TA menu that we were excited about eating only to...More

Thank Batt2
Reviewed 5 weeks ago via mobile

We just enjoyed one of the most pleasant dining experiences we have had in many years. Visiting Annapolis by boat, I called O'Leary's to ask about dinner availability - Will, the owner, was so pleasant & inviting on the phone that we had to try...More

Thank Mary F
Reviewed 15 May 2017

First, the shrimp and grits that was had by my friend were excellent. However, the Eggs Benedict with large lump crab cakes was another story. The crab cakes were just about non-existent about the size of a 50 cent piece and less than a 1/4"...More

Thank ScotVA
Reviewed 13 May 2017

I've been having dinner regularly at O'Leary's for 25 years...maybe a little longer. It has always been a wonderful, friendly experience. This is an intimate restaurant that is just large enough to hold about 75 diners at one time but still achieves a wonderfully small...More

Thank Roadwarrior098
Wil P, Owner at O'Leary's Seafood Restaurant, responded to this reviewResponded 15 May 2017

Thank you, my friend! We'll see you soon!

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Nearby Attractions
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.53 km away
St. Mary's Church
66 reviews
.59 km away
Annapolis Maritime Museum
73 reviews
.63 km away
Annapolis Summer Garden Theatre
20 reviews
.66 km away
Questions & AnswersAsk a question
Where can we park?
17 February 2017|
Answer Show all 3 answers
Response from Wil P | Property representative |
I have 2 parking lots on either side of the restaurant.
It is my Wife, Patty's, birthday today. Appreciate your noticing it. Our reservation is for 6:45 PM tonight. Lynn R. Frary, MD
25 January 2017|
Answer Show all 2 answers
Response from ltritz | Reviewed this property |
VERY attentive!
Is there a private area, where 18 people could enjoy dinner, without disturbing other diners?
9 November 2016|
Answer Show all 3 answers
Response from Wil P | Property representative |
Yes. I have a smaller dining room that can accommodate up to 25 people... If you want to discuss further, call the restaurant at 410.263.0884. Ask for Wil
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Restaurant Details

Rating summary
  • Food
  • Value
Average prices
US$28 - US$37
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
Special Occasion Dining, Local cuisine, 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
  • E-mail
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