O’Brien’s Oyster Bar & Seafood Tavern

On a cold and rainy afternoon at the Chesapeake Bay Media offices in Eastport, I found publisher John Stefancik scrounging around in the kitchen looking for sustenance. I was in need myself, so we headed over the bridge to downtown Annapolis to O’Brien’s Oyster Bar and Seafood Tavern to grab lunch.

We were quickly seated and our server, Markia, greeted us and took our drink order. I was thrilled to see a Greg Norman wine on the menu—I’m a fan of their blends and cabernet sauvignon—and ordered a glass of the shiraz ($12). It was a great choice, featuring bright aromas, black cherry and cloves. John opted for a black and tan, a combo of Yuengling lager and Guinness stout ($7), which he was happy with.

We decided to split an order of oysters Rockefeller ($17.95) as an appetizer. I love oysters, but oysters Rockefeller is not at the top of my list of preparation choices. That changed after thoroughly enjoying the version at O’Brien’s. 

Oysters Rockefeller

Broiled local oysters were topped with creamed spinach, Pernod, Parmesan cheese and hollandaise sauce. John and I agreed that it was the best version of oysters Rockefeller we’ve both tried. The best way to describe the dish is “crave-able.” The creamed spinach was good enough to be a side dish in its own right.

Markia was very knowledgeable about the menu and was able to answer all questions we had regarding ingredients, level of spiciness, etc. We both took note of the friendliness of the staff and how happy they all seemed to be part of the team at O’Brien’s, which made the afternoon that much more enjoyable.

Cajun seafood pasta

Based on Markia’s recommendation, John chose the spicy Cajun seafood pasta ($31.95). Penne is tossed with shrimp and scallops in a spicy Cajun cream sauce. John has been spending a good amount of time in New Orleans lately so he’s been on a spice kick. He declared this a great dish, with the perfect level of spice. “The scallops are juicy; the pasta is cooked perfectly and there’s a hint of pepper—which I love,” he said. 

I opted for the crabcake sandwich ($24.95, top photo). Jumbo lump crab is topped with lettuce and tomato and served on a toasted potato roll with fries. The crabcake was large and consisted of chunks of lump and very little filler—just enough to bind. It came with both tartar and cocktail sauce, but I used tartar. The potato roll was perfectly toasted and the fries were a good-sized portion. 

We were too stuffed to try dessert, but we did decide to explore upstairs—we both realized that despite growing up in Annapolis, we’d never ventured to the second floor. We were surprised to discover a wine bar, a banquet room and what used to be a cigar lounge, now used for fantasy league draft nights (email [email protected] if you’re interested in booking).

As we headed back out into the cold and rain, I glanced back at the bar and realized a perfect evening would be splitting oysters Rockefeller over wine with a date.

A few other things not to miss are 99-cent oyster nights Monday through Thursday 3 p.m. to 7 p.m. and all day Wednesdays; happy hour 2 p.m. to 7 p.m. Monday through Friday, and O’Brien’s “Fast Lunch Specials” Monday through Thursday from 11 a.m. to 4 p.m. 

Krista Pfunder grew up in Davidsonville and attended St. Mary’s in Annapolis. She graduated from Randolph-Macon College in Ashland, Va., where she was editor of the newspaper.