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Among the many luxury hotels in Maryland, there’s only one luxury boutique hotel on the state’s Eastern Shore that’s Black-owned and that is Great Oak Manor. After months of searching for properties from Georgia to Virginia, husband-and-wife team Werten Bellamy, Jr. and Kellye Walker found Great Oak Manor with the help of a consultant.
Located in the small city of Chestertown, about two hours from Baltimore, the property has gorgeous views of the Chesapeake Bay, which was one of the attractions for the owners. “Our property has a 12-acre lawn on a 25-foot bluff, overlooking the bay with sunsets behind the house every night,” boasts Bellamy, who is originally from Reston, Virginia.
The History of Great Oak Manor
The land the luxury boutique hotel sits on dates back to the 17th century and the owners have the maps to prove that it was once a plantation. “We consider ourselves stewards of this great property, which dates back to 1658,” Bellamy shares.
“We have 300- and 400-year-old trees on our property that we know our [enslaved] ancestors also looked at. And they never would have imagined that we’re here as owners of this property,” he adds with emotion.
The Georgian-style manor was built in 1938 and became Great Oak Manor Lodge, one of the country’s leading sportsman’s retreats, with guests including actor Robert Mitchum, golfer Sam Sneed, musician Guy Lombardo, and President John F. Kennedy, with many of them in photographs lining the manor’s walls today.
Bellamy and Walker purchased the property in 2022, and after hosting 27 weddings inherited from the previous owner, they completed renovations the manor in 2024. Although the couple boasts impressive resumes—having been leaders at international companies, board of directors and the U.S. Army—they say they needed to build a team of experts in the luxury hospitality field to help them execute the high level of service to their guests.
Why Guests Call it One of the Best Luxury Hotels in Maryland
Bellamy and Walker say when guests come to Great Oak Manor, they want them to have a very personalized experience and feel like family. “When you arrive, our staff meets you at your car, brings your bags to your room, gives you a personalized tour and helps orchestrate your agenda for your stay,” Bellamy explains.
“If Werten happens to be there when guests are checking in, he’ll say, ‘Welcome home!’ and you can see how guests just melt into that,” exclaims Walker, who is originally from Little Rock, Arkansas.
Guests also melt into the king-sized beds in their nine spacious rooms and three suites, which have all of the amenities of a luxury property, including some with fireplaces. “One of the things we hear consistently is how comfortable the beds are,” says Walker.
“There’s something about our mattresses and sheets where literally every guest tells us about how well they rest,” the Louisiana Tech University and Emory University Law School graduate says with pride. She continues, “We renovated all the rooms, so each one is uniquely designed and decorated very elegantly. Some have soaking tubs, some have showers, and a number of our rooms have fireplaces.”
The rooms at the back of the house overlook the beautiful Chesapeake Bay.
And there’s a cherished item that other luxury hotels in Maryland don’t have. “We have a painting called ‘Hope,’ which is a beautiful, seven-feet-tall African American woman that is featured in our parlor and it speaks to all of our guests,” says Bellamy with pride.
“That’s something you rarely see in a luxury property and it’s our way of signaling what we honor and what we see as power, beauty and grace, without saying a thing,” adds the Princeton University and University of Virginia Law School graduate.
Unlike most luxury hotels in Maryland, Great Oak Manor boasts a beautiful library, featuring books from award-winning Black women authors who have participated in their annual Freedom Writers Retreat.
“We partnered with our friends and authors Natalie Baszile, who wrote the book ‘Queen Sugar,’ which was made into a popular TV series and Lauren Francis Sharma, whose books include ‘Till the Well Runs Dry,’ notes Walker. “And we’re proud to have curated the first of its kind writing retreat for established Black women authors. It’s by invitation only and you have to have published at least two books,” she explains.
Ten authors are invited to spend ten days at the luxury boutique hotel.The retreat includes private time to write with boxed lunches provided, sessions where the authors do readings and share the writings they’re working on, and each night they enjoy a family-style dinner together.
“It’s in its third year and the sharing and laughter among the women has been extraordinary,” Walker exclaims. In fact, they are now planning an Emerging Writers Retreat for February 2026.
Connection, Learning and Wellness
Bellamy says, “There’s something powerful in putting people in connection with each other, in ways that maybe they might find difficult themselves.” That’s why he and Walker are very passionate about focusing on three areas with their guests: connection, learning and wellness.
Bellamy explains how their ‘Taste of Great Oak Manor,’ culinary experience combines learning and connection. “After guests arrive on Friday, our team makes dinner, that evening we gather in a large room which we call the conservatory and we do a fireside chat with our guest chef. The next morning, our team makes breakfast, then mid-morning, we go into our carriage house kitchen, which is tricked out with TV monitors and high directors’ chairs.”
He continues, “We typically have a guest load of about 20 to 26 people and the guest chef will do an interactive demonstration, much like you would see on TV. We have cameras over the burners and over every cooking and cutting service. Then, after a lunch break and some private time, we come back to the carriage house with a hands-on experience with pairs or groups of three. Connection preparing a dish under the supervision of our guest chef, which will lead us into dinner that evening, which we serve family style—again connection—and that dinner is prepared by our guest chef. And by this time, people have formed some connection with each other.”
“We have done this a number of times and it is, dare I say, magical,” exclaims Walker. “To hear the conversations, to hear the laughter, to see the connections that have come from that [culinary] learning experience is pretty phenomenal!”
She adds, “For our wellness space, we have two women’s wellness packages. One is called ‘StressLess Retreat’ and it is really focused on helping women to learn skills and techniques to destress in life. That retreat includes guided meditation, yoga, and we have a physician who is trained in helping women work through stress and we also include healthy foods for the meals.”
She continues, “The second wellness experience is called ‘My TYM Retreat’ and TYM stands for tea, yoga and meditation. We have guided meditation, then we have a woman who calls herself a Tea Huntress who takes us on a journey of the history of tea and how to use tea as a relaxation catalyst and how to have your own tea ritual.”
There’s also a joint cooking experience with their resident chef. “So that’s just another way for women to learn together and have that connection and focus on their wellness. And whenever we host these packages, the only people who are guests at Great Oak Manor for that weekend are here for that package experience,” she points out. The cost of the packages includes lodging, the experience fees and meals.
The Advantages of Chestertown and the Chesapeake Bay
Along with its scenic views of the Chesapeake Bay, the owners of Great Oak Manor take advantage of its proximity to cities such as Baltimore, D.C., Philadelphia, New York and Richmond.
“Though we have some international guests from the Caribbean, the U.K., Canada and Mexico, we’re focused on really being the experience destination of choice among the 12- to 15-million people who are within driving distance of Great Oak Manor, because what people value increasingly is their time,” Bellamy admits.
“When you come here, you can start your experience within two to three hours of leaving your home and you can continue your experience well into Sunday without feeling the stress of having to get to the airport and get through TSA.” In fact, travelers who don’t want to drive, can park at their local airport and catch a Great Oak Manor limo to the luxury boutique hotel. “It’s $200 to get here by our limo from BWI Airport,” notes Bellamy.
The owners also want to take advantage of the 300 nearby farms in the area to provide farm-to-table cuisine for their diners. They are already taking advantage of serving fresh seafood straight from the Chesapeake Bay.
“Some of our popular seafood dishes are a halibut with a lemon-butter and white wine sauce and sauteed red snapper,” shares Bellamy. “And of course, you have to have Maryland crab cakes as a standard offering,” he smiles.
The owners also take advantage of off-property tourism. “We share a lot of information about historic Chestertown,” states Bellamy. “There’s a brochure for the very rich African American history in the city and a Black woman by the name of Airlee Ringgold-Johnson, whose father was the general manager of Great Oak Manor in the 40s, 50s and 60s, who does African American walking tours of Chestertown,” he adds.
“There’s a whole corridor that was at one time the Wall Street for African Americans in Chestertown and she can identify the homes where the merchants and professionals were.”
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Professional Development, Relaxation and Relationships
Bellamy says they’re not in the bed business, they’re in the experience business. “We’re trying to create an ecosystem where people can move closer to their goals at Great Oak Manor, whether it be to reconnect with loved ones, or accelerate their culinary learning, or it may be to bring their business team back to move forward on their strategic objectives,” he discloses. “And those are three areas where we know we consistently deliver well, with premium food, a premium experience and a place where you won’t be bothered.”
There are plans to take the luxury boutique hotel to the next level with a newly designed kitchen to get into the fine dining space and open it up to the public— and not just hotel guests— led by a new chef and construction of a new event facility to get back to hosting weddings.
Bellamy adds, “We spend a lot of time trying to understand what our guests hope to achieve during their time with us and we try to curate an experience to help get them there.” Like the husband and wife the Great Oak Manor owners saw dancing on the lawn. “When they came in, they said, ‘We haven’t danced like that for 30 years,'” Bellamy recalls.
“So we asked them about the music they used to dance to and that’s what we played throughout the house that weekend.” That’s how the Bellamy-Walker team builds relationships that make their guests feel like family and develops brand loyalty.
Walker emphasizes, “Our business relationships built on loyalty instead of just transactions are much more enriching and fulfilling for us personally, but it’s also a more sustaining business model.” Bellamy agrees, “We’re in the relationship business.”
Speaking of relationships, the owners want to pass down Great Oak Manor to their three children. Their oldest son, Werten III is already on the team as assistant general manager and daughter Erica wants to eventually lead their wellness programs. Werten believes, “There’s something powerful about business ownership and creating a legacy of hospitality that we’ve witnessed other families sustain over generations.”
When speaking of owning one of the top luxury hotels in Maryland, both Bellamy and Walker continuously say they’re blessed. Bellamy concludes, “We’ve been asked, ‘How long do you folks plan to be here?’ And my response is ‘At least 100 years.’”
For more information on Great Oak Manor, accommodations and its upcoming experiences, visit their website, Facebook and Instagram pages.
