Food & Drink

O’Brien’s Oyster Bar and Seafood Tavern

Honest Chesapeake Seafood

When we think back on our recent trip to Annapolis, we can’t help but revel about our fantastic dining experience. Do you have a favorite type of food? Did you know Maryland is known for their seafood? Luckily, for Shayla – we were surrounded by some of the freshest seafood in town at O’Brien’s Oyster Bar & Seafood Tavern

Annapolis has an abundance of history. O’Brien’s is located on 113 Main Street and has been around for over 200 years! What started as a pub – and gathering spot for both Royalists and Revolutionaries in the 1800s, quickly turned into the Sam’s Cafe – the only dining and dancing establishment in downtown Annapolis. After WWII, Sam’s Cafe turned into LaRosa – offering the first pizza pie in town. By 1964, 113 Main Street became the first Cabaret Theatre in the area. A few years later, O’Briens was established and quickly became a huge hit with its steak and seafood menu. Last year, they upgraded their focus on American Chesapeake Cuisine and have been a hit ever since.

We were fortunate enough to visit on a cool, Friday summer evening taking in the full downtown experience. The weather was perfect to take a stroll on the street and down by the water. From the moment we walked into O’Brien’s – we got the feeling of a very welcoming, homey, entertaining setting. And that feeling did not go away – from the friendly host leading us to our table to the accommodating server who waited on us. The evening just kept getting better from there!

We were given some fresh bread and we ordered some mozzarella sticks to start so the kiddos could munch on something while we waited for some fruity drinks! Katie had the Italian Surfer and Shayla went for the Electric Lemonade. The yummy drinks were fruity and refreshing after a long day at Six Flags America (20 minutes outside of Annapolis). As we drank our drinks and had some mozzarella sticks, we watched some men carry in some equipment. We asked our server about the entertainment and in fact, there was a band playing that evening for a nightlife crowd! If we didn’t have the boys in tow, we would have definitely stayed for some live music! Who doesn’t love a live band?

Now for the entrees – the kiddos got an order of chicken fingers and french fries and the portion was gigantic to both to share! Katie ordered the filet mignon that was cooked exactly to her liking and she ate every last bit of it! Shayla opted for the mac and cheese with lump crab. She was a happy camper to change up her usual, lobster mac and cheese with the crab meat – it was a pleasant surprise and she ate her entire plate!

We clearly had full bellies with all of that delicious food! BUT, we could not pass up the dessert menu! The triple chocolate mousse cake was calling our names since before we even ordered our food! Come on, as a foodie – you gotta always check the desserts first to know how much to save room for! Ha ha! And that cake was to die for – so moist and what a lovely presentation. We were so impressed by how all of the food was presented and now the dessert was so awesome too!

When we walked out of O’Brien’s – the town of Annapolis was definitely happening. You had the hip youngsters mixed with a middle aged generation of folks walking up and down the street – some coming into O’Brien’s while others finding their casual drink destination. If you want to hit up Annapolis on your bucket list, definitely check out this area – so much excitement and yet when you walk into a restaurant/bar like O’Brien’s – you feel like you are right at home!

A huge thank you to Lisa for having us! The hospitality and kindness does not go unnoticed. The staff and good vibes shined through from start to finish! We cannot thank you all enough for a wonderful experience while visiting Annapolis.



Katie and Shayla

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