Exploring The Shore: Great Oak Manor In Chestertown, MD

Spring inspires us to adventure more and explore all that the Eastern Shore has to offer…and believe us when we say there is SO much to explore. Just when we think we’ve uncovered every park, attraction, and quaint hideaway, we stumble upon another! Our most recent discovery is situated on the upper part of the Eastern Shore in Chestertown, MD – Great Oak Manor. A historic bed & breakfast sited on a bluff on the banks of the Chesapeake Bay just eight miles from Chestertown, Great Oak Manor has been a B&B since 1946, with bragging rights to famous guests over the years including John F. Kennedy and Ernest Hemingway. We had to learn more…

Great Oak Manor is a historic, 12-guest room Georgian style manor built in 1938. Most recently, ownership changed hands, with Kent County resident Buddy Reed partnering with Mike Kuhn to taken over the historic property. “My dad was a Washington College graduate, and I’ve been coming to the area for years. My wife and I bought a home near Great Oak a decade ago – when I first saw Great Oak Manor, I was really impressed, and dreamed about the possibility of owning it some day,” says Reed. “When it came on the market again, my partner and I jumped on the opportunity. We’re thrilled to be stewards of this magnificent inn.”

The historic, family AND pet friendly property includes 12 guest rooms – six with fireplaces – each complete with private en suite bathrooms, hair dryers, high definition flat screen televisions, robes, DirecTV, and robes. A full, hot breakfast is served daily, along with afternoon refreshments. Picnic baskets featuring hand-crafted sandwiches, cookies, fresh fruit, beverages and wine are also available for purchase.

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