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By Mary Lou Baker
brPhotography by Tony Lewis, Jr.
Make a list of the qualities you look for when choosing a restaurant for a special occasion—and chances are they’re a match with the “new” O’Learys in Eastport. “New” is a reference to changes introduced by Wil Peterson, who leap-frogged from general manager to owner when he bought the place in 2016. Peterson, who had made a lot of friends in his 10 years as a stalwart O’Learys staffer, quickly put his own imprint on the place.
Evidence: whimsical underwater-themed paintings by local artist Charles T. Lawrance and photographs by Annapolis-based photographer Rachel M. Fry have replaced the previous owner’s personal collection; Sunday Brunch, featuring Bloody Marys gussied up with a shrimp, a crab claw, and a sprig of fresh basil, from 10 a.m.–2 p.m.; along with these enhancements, Chef Ezra Countiss III, a graduate of Johnson and Wales Culinary College in Providence, Rhode Island, has earned high marks since joining O’Learys’ team in 2017.
Apart from these notable improvements, nearly everything else stays the same at this longtime local favorite, founded in 1983 by Annapolitan Tom O’Leary. O’Leary moved on, founding Chevy’s Fresh Mex in Annapolis and soon adding two other Maryland locations. He and Peterson remain friends and share a serious commitment to customer service. If you go, expect to be greeted at the door by Peterson himself, then ushered to your table and introduced to your server. Staff members are seasoned professionals, hired on the basis of their experience and ability to measure up to Peterson’s standards.

We were seated in a quiet room behind the busy bar, under a painting entitled “Kissing Fish.” The restaurant seats 75 in this area and in the main dining room where booths and tables are reflected in a wall of mullioned windows. O’Learys bar was abuzz on our visit, with folks sipping craft cocktails created by Peterson and his colleagues. Reading the colorful descriptions of the unique aperitifs, I was amused to see that most of them called for citrus accents and sounded downright delicious. I later learned these recipes were created by Peterson, whose motto is “a good cocktail begins in the kitchen.”
Upon seating, we were served warm rolls and herb-seasoned butter as well as goblets of chilled water. My dinner companion gave high marks to his house-brewed iced tea while I marveled at the quality (and the prices) of O’Learys wine list. Reading it is educational, with top drawer choices from France, Spain, Italy, New Zealand, Argentina, Chile, Portugal, Germany, South Africa, and California. They are divided into groupings of “Bubbles and Whites” and reds with a separate category for half-bottles—most priced in the popular $30 range. There are a few wines by the glass and I was happy with a Folonari pinot grigio ($8/$31). Peterson hand-picked the wine—and obviously has superb taste. Hint: all wines are half-price on Tuesday and there is a fine selection of a dozen well-priced brews representing a handful of states and styles.
On to the menu, a seafood-lover’s delight. One could dine happily from an appetizer menu that includes salads, smelts, mussels, tuna tartare, calamari, oysters (fresh or grilled), or the single grilled jumbo diver scallop sitting proudly on the center of a small plate. Tender and as pristine as new snow, its ocean-tinged flavor was set off with a sweet mayo sauce and a soupcon of warm bacon jam—and invention of the chef. My partner and I shared a huge bowl of small but sweet Maine mussels in a remarkable sauce reminiscent of the creamy scallop soup called billi-bi.
Peterson is particular about the quality of his fish, counting on a Maine supplier for his lobsters and mussels and another source for the sustainable fin fish listed on the menu. In addition to red snapper, rockfish, mahi mahi, shrimp, bronzini (the chef’s choice on the evening we were there), diners have a choice of four “simple fish”—two white fish (barramundi and gulf corvina), Ahi tuna from Hawaii, and Atlantic salmon. Diners choose from five individual preparations or can simply choose from the menu entrees, as we did.
My friend was delighted with the chef’s signature dish called “crispy rockfish” because it is flash fried and lends itself to a whimsical presentation that involves standing pieces of bass over a mound of black beans and rice embellished with cilantro-flavored salsa and a couple of sautéed shrimp. Add to that mix a dash of barbecue sauce and all the taste buds are satisfied. I am a fan of simply broiled fish (especially swordfish fresh out of the sea) and ordered red snapper. When the plate arrived, the snapper was arranged in pieces on a puree of orange butternut squash, a mound of roasted cauliflower with caramelized onions and a forest of carrots glazed with honey precariously perched on the side. Lot of good food all at once—and Jennifer, our delightful server, brought out a take-home container. I imagine it’s fun to work in O’Learys kitchen.

We finished a huge and varied meal with the restaurant’s legendary warm bread pudding and a fancy house-made chocolate tuile filled with rich chocolate mousse, drizzled with raspberry coulis, and finished with fudge sauce and real whipped cream. Our experience as pampered guests in the homey cottage made us eager to return—maybe on a Tuesday night when I’m not in working mode and the wine is half price. And there’s more—the chef offers a special three-course prix-fixe menu for $39. Welcome aboard, Wil—you are the captain of a very fine ship.
brPhotography by Tony Lewis, Jr.
Make a list of the qualities you look for when choosing a restaurant for a special occasion—and chances are they’re a match with the “new” O’Learys in Eastport. “New” is a reference to changes introduced by Wil Peterson, who leap-frogged from general manager to owner when he bought the place in 2016. Peterson, who had made a lot of friends in his 10 years as a stalwart O’Learys staffer, quickly put his own imprint on the place.
Evidence: whimsical underwater-themed paintings by local artist Charles T. Lawrance and photographs by Annapolis-based photographer Rachel M. Fry have replaced the previous owner’s personal collection; Sunday Brunch, featuring Bloody Marys gussied up with a shrimp, a crab claw, and a sprig of fresh basil, from 10 a.m.–2 p.m.; along with these enhancements, Chef Ezra Countiss III, a graduate of Johnson and Wales Culinary College in Providence, Rhode Island, has earned high marks since joining O’Learys’ team in 2017.
Apart from these notable improvements, nearly everything else stays the same at this longtime local favorite, founded in 1983 by Annapolitan Tom O’Leary. O’Leary moved on, founding Chevy’s Fresh Mex in Annapolis and soon adding two other Maryland locations. He and Peterson remain friends and share a serious commitment to customer service. If you go, expect to be greeted at the door by Peterson himself, then ushered to your table and introduced to your server. Staff members are seasoned professionals, hired on the basis of their experience and ability to measure up to Peterson’s standards.

O’Learys Seafood
310 Third Street, Annapolis. 410-263-0804. Olearysseafood.com. Dinner Sun.–Thurs. 5–9 p.m., Fri.–Sat. ’til 10 p.m.; Sunday Brunch 10 a.m.–2 p.m. Reservations recommended; private parties accommodated. Major credit cards accepted. Handicapped accessible.
310 Third Street, Annapolis. 410-263-0804. Olearysseafood.com. Dinner Sun.–Thurs. 5–9 p.m., Fri.–Sat. ’til 10 p.m.; Sunday Brunch 10 a.m.–2 p.m. Reservations recommended; private parties accommodated. Major credit cards accepted. Handicapped accessible.
We were seated in a quiet room behind the busy bar, under a painting entitled “Kissing Fish.” The restaurant seats 75 in this area and in the main dining room where booths and tables are reflected in a wall of mullioned windows. O’Learys bar was abuzz on our visit, with folks sipping craft cocktails created by Peterson and his colleagues. Reading the colorful descriptions of the unique aperitifs, I was amused to see that most of them called for citrus accents and sounded downright delicious. I later learned these recipes were created by Peterson, whose motto is “a good cocktail begins in the kitchen.”
Upon seating, we were served warm rolls and herb-seasoned butter as well as goblets of chilled water. My dinner companion gave high marks to his house-brewed iced tea while I marveled at the quality (and the prices) of O’Learys wine list. Reading it is educational, with top drawer choices from France, Spain, Italy, New Zealand, Argentina, Chile, Portugal, Germany, South Africa, and California. They are divided into groupings of “Bubbles and Whites” and reds with a separate category for half-bottles—most priced in the popular $30 range. There are a few wines by the glass and I was happy with a Folonari pinot grigio ($8/$31). Peterson hand-picked the wine—and obviously has superb taste. Hint: all wines are half-price on Tuesday and there is a fine selection of a dozen well-priced brews representing a handful of states and styles.

On to the menu, a seafood-lover’s delight. One could dine happily from an appetizer menu that includes salads, smelts, mussels, tuna tartare, calamari, oysters (fresh or grilled), or the single grilled jumbo diver scallop sitting proudly on the center of a small plate. Tender and as pristine as new snow, its ocean-tinged flavor was set off with a sweet mayo sauce and a soupcon of warm bacon jam—and invention of the chef. My partner and I shared a huge bowl of small but sweet Maine mussels in a remarkable sauce reminiscent of the creamy scallop soup called billi-bi.
Peterson is particular about the quality of his fish, counting on a Maine supplier for his lobsters and mussels and another source for the sustainable fin fish listed on the menu.
Peterson is particular about the quality of his fish, counting on a Maine supplier for his lobsters and mussels and another source for the sustainable fin fish listed on the menu. In addition to red snapper, rockfish, mahi mahi, shrimp, bronzini (the chef’s choice on the evening we were there), diners have a choice of four “simple fish”—two white fish (barramundi and gulf corvina), Ahi tuna from Hawaii, and Atlantic salmon. Diners choose from five individual preparations or can simply choose from the menu entrees, as we did.
My friend was delighted with the chef’s signature dish called “crispy rockfish” because it is flash fried and lends itself to a whimsical presentation that involves standing pieces of bass over a mound of black beans and rice embellished with cilantro-flavored salsa and a couple of sautéed shrimp. Add to that mix a dash of barbecue sauce and all the taste buds are satisfied. I am a fan of simply broiled fish (especially swordfish fresh out of the sea) and ordered red snapper. When the plate arrived, the snapper was arranged in pieces on a puree of orange butternut squash, a mound of roasted cauliflower with caramelized onions and a forest of carrots glazed with honey precariously perched on the side. Lot of good food all at once—and Jennifer, our delightful server, brought out a take-home container. I imagine it’s fun to work in O’Learys kitchen.

We finished a huge and varied meal with the restaurant’s legendary warm bread pudding and a fancy house-made chocolate tuile filled with rich chocolate mousse, drizzled with raspberry coulis, and finished with fudge sauce and real whipped cream. Our experience as pampered guests in the homey cottage made us eager to return—maybe on a Tuesday night when I’m not in working mode and the wine is half price. And there’s more—the chef offers a special three-course prix-fixe menu for $39. Welcome aboard, Wil—you are the captain of a very fine ship.