Annapolitan Institution

By Tom Worgo | Photography by Stephen Buchanan

Konstantinos “Kostas” Alexakis bought O’Brien’s Oyster Bar & Seafood Tavern in the heart of downtown Annapolis in early 2018. The property has a history as a popular eating and meeting place that goes back almost two and a half centuries.

During the Revolutionary War, it was a hotbed of intrigue for both the revolutionaries and the opposing royalists. Alexakis pays tribute to its past on his website and appreciates the location’s historic importance.

“It’s part of Colonial Annapolis, old Annapolis,” Alexakis says. And it’s not even just O’Brien’s anymore. “It used to be more of a bar,” Alexakis recalls. “Now, we are a restaurant. We are not a pub, but the bar is still part of the business.”

Growing up, Alexakis worked at family-owned restaurants in Northern Virginia. After college, he opened Eve’s French Bistro in Rosalyn, Virginia. Later, he owned two restaurants—Tex-Mex Grill and Big Bubba’s Barbecue in Baltimore’s Inner Harbor.

After he sold the Baltimore restaurants, he made an unsuccessful bid for a U.S. Congressional seat. Since 2018, he’s been committed to making a lot of changes to what is now O’Brien’s Oyster Bar & Seafood Tavern.

Among the biggest improvements include renovating the upstairs banquet room, bringing in Executive Chef Scott Hamilton last year, overhauling the kitchen, and expanding the menu with more seafood items.

Customers snatch up crab cakes, rockfish, shrimp, and seafood appetizers, among other popular items. The restaurant also features a deejay on Friday and Saturday nights when lines form out front door. As in the past, the establishment continues to be populated with a heavy Naval Academy presence. “It’s known throughout the world because it caters to so many Navy events,” Alexakis says. “All the admirals that have passed through Annapolis have been to O’Brien’s.”

We recently talked to the Severna Park resident about what keeps customers coming back, guests’ favorite foods, and the menu.

How do you keep customers coming back? Quality food and service. The service remains high. We are diligent when it comes to keeping those things going. It’s consistency. It’s word of mouth. We are focusing on fresh fish, oysters, filets, rib-eyes, and strip steaks. They are all prime. We keep that consistency and that’s why people come in.

What kind of customers do you attract? For dinner, it’s a 35 to 50-years-old crowd. We have local customers during the week and then the tourists come during the weekends. Those are the different types of customers. Our goal is to keep the locals happy because they are our reliable customers. We also appeal to the tourists who are just looking for a quality place to eat on the weekends. We want to become a seafood destination restaurant. We added seafood to the restaurant’s name to highlight the seafood. Our business has tripled in the last four years.

What are your top-selling items? Probably crab cakes. There is lump crab meat and no filler. It has the sweetness of a crab with a little bit of Old Bay. Most people find it outstanding and are impressed with it. I love the crab cakes. We have local rockfish and serve it with crab imperial, a little lemon, and olive oil. We broil it. It enhances the flavor. It’s terrific and probably our number two seller.

How would you describe the menu? The focus is on seafood. That’s the key for us. We carry six different fishes: grouper, tuna, sea bass, cod, rockfish, and salmon. You can’t find anybody that has the choices that we do. We also offer three oysters and an evolving fourth oyster. Every month there is a different one. In downtown Annapolis, restaurants are competing with the same kind of things: cheeseburgers, salads, and chicken wings. With our menu, we are focusing on seafood like crab cakes, oysters, scallops, and mussels. The quality of every item on the menu is superior to everyone else. For example, we have our streamed shrimp. You will be impressed by it. Everywhere else you go in Annapolis, the steamed shrimp are smaller. Also, the banquet menu and the room are beautiful. We can craft the banquet menu to whatever the customer wants.

Where do you source your food from? We get our steaks and all our meats from a high-end place in Fells Point, Baltimore, Wholesale Meats. It’s the best. The oysters come from the Eastern Shore. We get our seafood from several different vendors. Seafood has a very short shelf life, so we get it fresh from Maryland vendors.

Can you talk about your restaurant’s involvement in the Oyster Recovery Project? We generate a lot of oyster shells and donate them. We serve the most oysters in Annapolis. It’s a great idea and I am happy to be part of it. The Oyster Recovery Project makes sure that we have oysters in the Bay. The oysters are necessary for the water quality. It builds oyster beds over time. It’s necessary for them to have the oyster shells to do that.

Tell me about your involvement and partnership with Annapolis Ghost tours and paranormal funhouse. It’s a wonderful group. They take tours all around Annapolis and get access to buildings all over. You hear about these different stories about ghosts and we participate as best we can. They come by a couple of times a week on tours. We allow them to use the banquet room upstairs to tell their stories. There’s a good synergy in working with them. It’s part of the local culture.