Twenty minutes northwest of Chestertown, and down a hilly, narrow road that ends up as a gravel driveway, a stately brick manor house rises over sweeping lawns and Adirondack chairs overlooking the Chesapeake Bay.

At first glance, it is easy to imagine Jack Kennedy or Ernest Hemingway toasting a Bay sunset with raised brandy snifters.

According to manor house history, they were guests, along with Arthur Godfrey, Guy Lombardo, and Robert Mitchum, who might have taken advantage of the property’s private airfield, one of the few on the Eastern Shore in its day.

You have just discovered Great Oak Manor.

Originally built from ships’ ballast bricks in 1938, the 12,000 sq. ft. The Georgian-style house was designed as a private residence for Russell D’Oench, heir to the W. R. Grace shipping line. 

After several ownerships throughout the decades, Great Oak Manor was recently purchased by husband and wife, Werten F.W. Bellamy and Jr. Kellye L. Walker, who saw in the Manor a unique opportunity in line with their desire to offer a boutique hotel and elegant retreat for corporate professionals to hold learning seminars in a restorative environment, while also continuing as a hotel for travelers looking for an idyllic and plush Chesapeake Bay retreat.

The couple, both with extensive  backgrounds in corporate law, look to Great Oak Manor as a commitment to focusing on “the vital role strong relationships play in both people’s personal and professional lives,” and for those “who need smaller scale, restorative environments to support and further develop their relationship needs.”

“Our goal is to build loyal guests, not scale. We want the Manor to be a place where our guests can focus on the things that matter,” they write in the Manor prospectus.

Here, the Spy sat down with General Manager Brooks Bradbury, who brings decades of experience in the hospitality business to the new venture.  

We welcome Kellye Walker and Werten Bellamy to the Eastern Shore and congratulate them for breathing new life into an architectural treasure. 

This video is approximately six minutes in length. For more about Great Oak Manor, go here.

The history of enslavement—and dramatic escapes—is part of the Eastern Shore’s DNA. Go no farther than Harriet Tubman and Frederick Douglass to recognize their celebrated quests for freedom and to understand subjugation on the 19th Shore, an inequality still a burning thread in the fabric of our lives.

Chestertown has its own chapters to add to the growing canon of great escapes. One of them is the story of Issac Mason, an enslaved man who fled his bondage in 1846, now told in a new musical as a reading.

The original musical “ISAAC: A Musical Journey,” written by Kent County native Marlon Saunders will premiere at Washington College’s Gibson Arts Center on June 24, 25, and 26 and promises to be one of the season’s most heartfelt and entertaining theatrical events.

KCA states, “This production will feature Paris Nesbit (Broadway: Book of Mormon) as ISAAC, Sue Matthews as Enslaver Hannah Woodward, and Kelly Sloan as the Ancestral Goddess. The reading will be supported by musicians Marlon Saunders (Composer), David Inniss and Eric Brown. The premiere is being directed by Biti Strauchn and produced by John Schratwieser.”

Commissioned by the Kent Cultural Alliance (KCA) for the Chesapeake Heartland Project at Washington College, “ISAAC” is based on the autobiography “Isaac Mason as a Slave.”

New School Jazz writes,” Marlon Saunders, former professor and alumnus of Berklee College of Music, is the founder and CEO of The Seamless Voice, a vocal and artist-coaching studio in New York City. As a vocal coach, Marlon works with artists from all major recording labels and has Broadway artists currently in Hadestown, Ain’t Too Proud, Frozen, Kinky Boots, Beautiful, The Lion King, and Book of Mormon. Marlon has toured with Stevie Wonder on The Songs In The Key of Life Tour. He was also the vocal contractor for Sam Smith and Bastille, Logic and Mondo Cozmo.”

In a recent interview with the Spy, Marlon Saunders talked about his youth in Chestertown, his early musical influences, life beyond Kent County and entering the professional world of musicians, and, of course, the composing of “ISSAC: A Musical Journey.”

For more about Kent Cultural Alliance and tickets go here. For more about the Chesapeake Heartland Project, go here.