Great Beginnings The pristine landscape that surrounds Great Oak dates back to the 1600's where Lord Baltimore granted the land to Joshua Felton and Marmaduke Tylden. In 1938, Russell D'Oench, an heir to the W.R. Grace shipping fortune, hired award-winningz architect Douglas Braik to design and build the 18th century Georgian-style house.

The Glory Days D'Oench sold the property to Frank Russell, CEO of Rusco Storm Windows, Inc. The year was 1946, and Russell had grand plans for his new haven. The legend of Great Oak Farm & Lodge as one of the country's finest sportsmen's clubs was born. From golf, horseback riding, and duck and goose blinds for gunning, to an entire fleet of watercraft for fishing and yachting, Russell had quite a playground to entertain guests and friends. There was even a four-star restaurant and a private airport right on the premises. Here the power hungry of D.C. rubbed elbows with the glamour elite of L.A. Notable guests included Guy Lombardo, Robert Mitchum, and Jack Kennedy.

A Storied Past By the 1970's, jets made it easier for guests to travel to exotic lands faraway from the gentle shores of Great Oak, and Frank Russell found it hard to keep his dream alive. The estate was then sold to Mr Mallon of Main Steel for his business benefits program. He eventually sold off the land and the manor.

In 1983, a wealthy couple from Philadelphia couple purchased the Manor and restored it to its earlier glory. Great Oak opened its doors as a high-end bed and breakfast, catering to outdoor enthusiasts and couples seeking a romantic oasis. By the dawn of the 1990's the manor had once again fallen into disrepair and was put up for sale.

Two Californians looking to escape the corporate world purchased the manor in 1992. Thanks to Don and Diane Cantor, Great Oak Manor once again became the guest home where people could expect nothing less than unbridled comfort and gracious living.

Back to top of page Present Day After ten years, the Cantors were ready to settle down in Chestertown and started their search for new innkeepers.

Enter Cassandra and John Fedas, two travelers who couldn't ignore the Chesapeake's magnetism. They came from the small New England sailing town of Marblehead and they were ready to take their burgeoning architectural and design firm to warmer climes. They settled in Annapolis for 12 years, then decided to move to the Eastern Shore to recapture the small home town feel. Chestertown was love at first sight. They had built fine homes and a country inn in Marblehead. Cassandra had even owned a small B&B. And somewhere inside, they knew the banks of the Chesapeake are where they were meant to be.

Since 2002 Cassandra and John Fedas cared for Great Oak Manor with a kind of love the house has earned. Today they still wonder if they found Great Oak Manor, or if it found them. Back to top of page