Business Spotlights

Kitty Knight, LLC

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The White Swan Tavern

Nestled firmly in the heart of Downtown Chestertown, the White Swan Tavern has served as a humble beacon of the town’s history since the completion of the building’s restoration in 1981.

This date may be a bit misleading, insinuating that the Tavern is not in fact as old as we may think; however, the building itself has worn many faces and has had several additions since its beginning as the residence of the town shoemaker and tanner, John Lovegrove, in 1725. The most recent expansion of the tavern was completed in 1860, making even the newest portions of the building over 100 years old.

For a long time, the building served as a tavern, a public space to meet, and a place for patrons to stay, but, in 1850 the building was turned into shops, and as some may know, the P&E News agency, up until 1977 when restoration began.

“The White Swan is unique because we have been able to preserve so much of the architecture from the colonial period,” says Head Innkeeper Sarah Crump. “We have a museum in the tavern, showcasing only a few of the 70,000 pieces we found during the archaeological dig performed during the restoration. It’s special because it makes us part bed and breakfast and part museum, so we do general tours for overnight guests, but we will also guide much more in-depth educational tours to groups or those who are interested.”

Inside of the museum case at the heart of the tavern is a colonial era bowl, broken but glued back together. Inside it is carved to show the image of a bird and a date, 1730. This image is what inspired the name and logo for the newly renovated building, The White Swan Tavern.

“A lot of people don’t know that all this history is here, and some don’t even know that we’re still a functioning business,” Crump said. “We want to open up and do more. We have afternoon tea every day from 3 to 5, and we’re starting to add additional offerings. We’re not just a bed and breakfast, this is a multi-functional space, and we can do a lot of things with it.”

Back in the day, a tavern was a place where you might have gotten your information, food, made business deals, or act as a meeting space. Crump’s aim is to keep these core ideals alive within the White Swan, opening the doors not just to overnight patrons or other visitors, but members of the community as well.

The White Swan Tavern is located on High Street, right in the center of downtown Chestertown. This makes it a great destination for visitors, as there is little to no driving required once you get settled in at the tavern. But it is equally nice for locals, as they can easily stop by for tea and a historic tour during a town event or after the Saturday farmer’s market.

“We’ve been meeting a lot of our neighbors for the first time in 40 years,” says Crump. “On one hand, it’s great to meet all these people, but on the other, why did it take so long in the first place?”

Approaching the White Swan Tavern itself is a bit daunting, as entry requires you to press a doorbell as though requesting entry into someone’s personal residence. Crump said they aim to make the front door a bit more accessible and inviting, as employees have often found curious passerby peering into the windows, perhaps afraid to ring the bell themselves.

Once inside, you’re greeted with a view up the staircase where a huge 45-starred American flag is hung. Looking to either side you’ll find a variety of antique furniture, as though you truly have stepped into the past. At the back of the tavern the John Lovegrove room is tucked away, supported by the original wooden beams and fireplace that John Lovegrove built nearly 300 years ago.

It’s special to have such an intimate look at history without the overall feeling that you might break something, as you may feel in a museum. Crump even admits that before she started working at the White Swan Tavern she was not a fan of history, but being able to see it and touch it hands on sparked interest in her. Even patrons who stay at the tavern solely due to its location leave with a greater appreciation of colonial living thanks to the experiences the White Swan Tavern provides.

“Starting next year, we want to do a monthly tea and talk,” Crump said. “We want to invite local authors, artists, or other notable figures, and just chat over tea in an informal setting. Some businesses have even approached us with interest in doing collaborative shoots, or wine tastings.”

Crump says to expect to see more from the White Swan Tavern, from larger events like a Dickens of a Christmas and a Murder Mystery event on New Year’s Eve, to an active participant in First Friday! If you haven’t already, drop by for a tour of the place and stay for afternoon tea!

For booking information, call 410-118-2300, or visit