Once a Chesapeake Bay playground for visiting VIPs including John F Kennedy and Ernest Hemingway, Great Oak Manor has a new owner. Kent County resident Buddy Reed and partner Mike Kuhn completed a deal last month to acquire the historic 12-guest room Georgian style manor built in 1938.
Sited on a bluff on the banks of the Chesapeake Bay just eight miles from Chestertown, the manor was originally built as a private residence but has served as a B&B since 1946. Reed brings decades of resort and hospitality experience to his new venture and plans to maintain the property as a B&B and position it as a premier destination for weddings, corporate retreats and group rental. “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.”
Reed and his team have completed interior improvements, including renovating a former spa and pool area into an elegant lobby and atrium that provide stunning views of the Bay. The space is now fit for receptions and events. Ground improvements have commenced and will be completed by spring. Additional outdoor seating areas will feature fire pits and Adirondack chairs.
Centrally located on Maryland’s upper Eastern Shore, pet-friendly Great Oak offers guests a convenient bayside location offering myriad recreational water activities – paddling around the bay in canoes or kayaks are popular pastimes – or visitors can dock their own boats at nearby Great Oak Landing Marina, a short walk from the manor. Sunset cruises are offered through Blue Crab Chesapeake Charters. A private beachfront below the bluff provides a secluded retreat to watch some of best sunsets on the bay or for a livelier time, guests can join the festivities at neighboring Jellyfish Joel’s, a tropical Tiki bar featuring live music on weekends or take in a casual meal at the marina’s restaurant. “People come to the Eastern Shore to experience the lifestyle,” says Reed. “The bay and region offer crabbing, fishing, hunting and boating which have been draws forever, but the area is also popular with nature enthusiasts and adventure travelers,” cites Reed who mentions the manor’s proximity to the Eastern Neck Wildlife refuge and the manor’s reputation as a haven for bicyclists.
The Manor supplies kayaks and bikes for guest use. “We’re also seeing an increasing amount of food and wine travelers,” says Reed noting the historic property’s central location along the Chesapeake Wine Trail, which currently features four wineries within 20 minutes of Great Oak (with several more local vineyards set to launch wineries) and a dozen or more wineries located within an hour’s drive. Reed is banking on further growth of Chestertown and Kent County’s agritourism efforts to draw out of area visitors.
Great Oak Manor is partnering with local and regional tourism groups to spotlight the region’s attractions including collaboration with the Kent County Tourism office and the Downtown Chestertown Association to promote the town’s well-attended weekly, monthly and annual events like the Saturday farmer’s market, arts-focused First Fridays and the Sultana Down Rigging weekend in November.
“We bring a love of the area and decades of construction and hospitality experience to our new ownership of Great Oak. We look forward to becoming part of the local community and showcasing the best that Chestertown and the eastern shore have to offer,” says Reed. Reed also notes that the new website will promote seasonal guest packages, feature an events page, newsletter, regular blog posts, and social media platform access.
Lawrence D'Oench says
Thanks for the article. My father and mother Russell and Faith D’Oench built this house and I lived there for a few years. Both my father and mother learned to fly there and used the runway they included in the construction so as to be able to visit Washington more frequently. Unfortunately WW2 interfered with our lives, they both went off to war, and their marriage didn’t survive. Thus Great Oak was sold. I’ve been back three times as an adult, including sleeping in the room I lived in as a child, and am ecstatic the place has new life.
Sam Ringgold says
The manor house holds a special place in my family’s life. My dad, Samuel Ringgold Sr. worked at Great Oak for many years both at the manor house and at the club. The stories he used to tell about his Great Oak days were legendary. Even though of course Dad was in a service role at the property he watched at the rich and famous came and went and hit drove his desire to provide a better quality of life for his family and that he did. The Russell’s held such a special place in Dad’s life. One year he rented the entire manor house to give Mom a birthday party. Imagine that, celebrating the matriarch’s birthday with family and friends in the house he once cleaned. It was an amazing day. Is the one guest room still named The Ringgold Suite? I recall the looks on my young kids faces when they saw it. I haven’t been to the manor house for a few years now but look forward to visiting soon.
Buddy Reed says
Thank you for the Comments. I am one of the new owners and would really like to have you to Great Oak. Would enjoy learning the History as you know it!
Buddy Reed
Sam Ringgold says
Hi Buddy, Me and my older sisters would welcome that. My oldest sister actually remembers attending Holiday parties in the manor house. I’ll call next time I’m headed to Chestertown.
Marty Stetson says
Great Oak Monor will always hold a special place in my heart as my first daughter got married there over twenty years ago. I have fond memories of walking down the steps of the manor and outside with her to be married. She has a birthday this week and among the many thoughts I will have of her will be that of the wedding and how nice it was at the Great Oak Manor. ( She is still married and the mother of two super kids ).