March 28, 2024
Annapolis, US 51 F

A few changes coming to the newly sold O’Brien’s

After nearly 25 years on Main Street, Annapolis restaurateur Jerry Hardesty has sold O’Brien’s Oyster Bar and Restaurant to Kostas Alexakis of Severna Park.

Hardesty, 76, is winding down his presence in the Historic District with the sale.  He still owns Middleton Tavern, which he opened in 1968, but is ready to scale back and enjoy semi-retirement.

Alexakis has an extensive background in the restaurant industry and is excited to become a part of the Annapolis dining scene. We spoke with Kostas this morning and he recognized the history O’Brien’s has played in Annapolis and has no plans to change the name. “O’Brien’s has a long history in Annapolis and one of the most overlooked aspects might be the fantastic kitchen.” Under Hardesty’s ownership, O’Brien’s somewhat played the role of “little brother” to the older, more iconic Middleton Tavern. Kostas continued, “We are cleaning up and making some changes to upgrade the experience—there will be a greater focus on seafood and the menu will be welcoming to everyone, families, couples, singles. We appreciate being a late night destination on Main Street, and plan to upscale our entertainment with more live music to broaden our reach, so that will be one of the changes.” Alexakis has carefully listened to, and appreciates the new Mayor’s efforts to make historic Annapolis the jewel of Maryland and consulted with the City and plans to coordinate with the City’s effort and will be moving forward to “fit the vision of the Mayor as a upscale dining destination for everyone.” And “Upgrading the outdoor seating will be a focus for us this spring.”

When asked about the upstairs room at O’Briens (once operated as OB’s Prime Steak House), Alexakis was coy, “We have plans. A fantastic new concept. But you’ll have to wait for that.”

The building was acquired in February and the business just conveyed this week.

Hardesty, 76, is winding down his presence in the Historic District with the sale.  He still owns Middleton Tavern, which he opened in 1968, but is ready to scale back and enjoy semi-retirement.

When taking over O’Brien’s is 1993, Hardesty gave it a Naval Academy flare.  Action pictures of USNA athletes adorn the walls and portraits of heroes line the bar.

For many years O’Brien’s hosted weekly live sports and political radio broadcasts.

O’Brien’s established a reputation for after dinner entertainment and activities with acoustic music in the bar and bands and DJs in the club.  Poker nights and tango exhibitions drew enthusiasts of all ages downtown.  Crowds were particularly lively during General Assembly sessions with contests like “Legislative Idol” on Monday nights.

O’Brien’s also hosted the iconic Santa Speedo run, which raised money for charity every Christmas season while providing plenty of cheer for participants and spectators.

Perhaps the greatest accomplishment in Hardesty’s tenure on Main Street was the introduction of sidewalk cafes.  During the reconstruction of Main Street in 1994, Hardesty petitioned the city government to permit him to add outdoor seating on the newly widened brick sidewalks.

The measure faced stiff opposition from downtown residents who feared rowdiness and expansion of bar capacity.  It was not until fall of 1995 that permission was granted for temporary seating outdoors.

The cafe was an immediate hit, particularly with families who found it convenient for strollers, wheelchairs and canines.  Within days, other restaurants applied for cafe licenses.

What was once a temporary permit has now become a mainstay in downtown dining, and one of the most popular attractions for tourists.

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