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O'Leary's Seafood Restaurant

££££American, Seafood,
310 Third Street, Eastport, Annapolis, MD 21403-2510
+1 410-263-0884
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  • Excellent63%
  • Very good23%
  • Average8%
  • Poor2%
  • Terrible4%
Travellers talk about
“rockfish” (34 reviews)
“seafood” (64 reviews)
“crab cakes” (74 reviews)
Open Now
17:00 - 21:00All hours
American, Seafood, Contemporary, Gluten Free Options, Vegetarian Friendly
310 Third Street, Eastport, Annapolis, MD 21403-2510
All Details
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Reviews (319)
Traveller rating
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151 - 160 of 318 reviews

Reviewed 27 December 2014

This was a return visit to O'Leary's for me (my honey was a first-timer). We were enjoying a quick get-away to Annapolis and I knew that I wanted to celebrate my birthday dinner at O'Leary's. We had their last reservations of the December evening so...More

1  Thank djvdw
Reviewed 21 December 2014

We just loved O'Leary's Seafood Restaurant, what beautiful decor, wonderful service and oh the food! We started out with calamari perfectly cooked yum and the fried grouper with jumbo shrimp was amazing! We can't wait to go back!

1  Thank Fcafc
Reviewed 12 December 2014

Best seafood restaurant in Annapolis. Black bean soup is amazing. All of the fish dishes come with multiple ingredients. So there is nothing boring about their entrees. Service is great. Ambiance lovely. This is a great place to bring out of town guests for a...More

1  Thank JaniceKosta
Reviewed 6 November 2014

Best variety and quality of seafood in Annapolis. They usually take reservations (recommend in summer). Pricey. Small, nice atmosphere. If you're looking for a more boisterous time eat at the bar at Ruth's across the street or Middleton's next to city market.

2  Thank Thomas L
Reviewed 3 November 2014

If you love fish and shellfish, O'Leary's should not be missed if you're visiting Annapolis. Quite small and a bit noisy because of it, that really should not be a deterrent to eating here. Tiny bar area, but with a reservation, you will be seated...More

Thank Pamela M
Reviewed 20 October 2014

The tables at O'Leary's are a little too close for comfort and it does make it feel a bit crowded, but the food was excellent... as were the cocktails :-) We had the shark, which was quite a small portion for the price to be...More

Thank Geoff and Jenni G
Reviewed 19 October 2014

We have eaten here in the past and have always found the food very good. The atmosphere is crowded and the seating is tightly packed. You essentially will have no privacy in your conversations. This is not a romantic couple restaurant. The restaurant is a...More

1  Thank L B
Reviewed 10 October 2014

First time in Annapolis and we were told o'Learys was the place to eat seafood. We made reservations and showed up on time. We were seated promptly and the waitress came right over to get our drink order, but I left my cheaters in the...More

1  Thank Slinginglead
Reviewed 2 October 2014

Loved the ambiance and the food...wines were amazing...martinis fully loaded with the best and biggest olives ever! My husband had the grouper...loved it...I had the crab cake and soft shell crab over fried green tomatoes...amazing! We can't wait to return!

Thank pattyden2
Reviewed 23 September 2014

Went to O'Leary's due to its top rating on Yelp, during a boat trip to Annapolis overnight with another couple. We couldn't stop talking about the meal that night or the next day. It was clearly one of the top two meals we've had this...More

1  Thank tankr
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Nearby Attractions
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.33 miles away
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.36 miles away
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.39 miles away
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.41 miles away
Ask a question
Questions & Answers
17 February 2017|
AnswerShow all 4 answers
Response from Wil P | Property representative |
I have 2 parking lots on either side of the restaurant.
25 January 2017|
AnswerShow all 2 answers
Response from ltritz | Reviewed this property |
VERY attentive!
9 November 2016|
AnswerShow 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
Local cuisine, Special Occasion Dining, Business meetings, 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
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