GO EAST(ERN)

Standing on the huge back lawn of Great Oak Manor, looking out at the Chesapeake Bay, it’s easy to imagine the others who used to come to this massive Georgian-style house for an under-the-radar getaway. Perched on the water just a few miles from Chestertown, the picturesque town founded in 1706, the manor came to life in the 1930s.

But it wasn’t until the ‘50s and ‘60s that the place became a haven for alpha males, ostensibly visiting the private club created here by Frank Russell, an entrepreneurial type who bought the private home in 1947 and turned it into a private sportsmen’s club, designed for men to escape the nearby big cities of Baltimore, Philadelphia, New York and Washington, D.C. for a weekend of hunting, fishing and sailing.

That’s when writer Ernest Hemingway turned up, soon followed by actor Robert Mitchum and eventually President John F. Kennedy and his cohorts often filled the three-story mansion’s bedrooms, which back then held a secret on the top floor. That’s where Russell ran his illegal casino, complete with gaming tables, pretty women and plenty of other distractions for the power players who came to stay.

Nowadays, that third-story eyrie is one of Great Oak Manor’s 12 elegant guest rooms, found up the sweeping staircase that leads to the upper floors (note that there is no elevator in this beautifully designed inn), where many rooms and suites have views of the bay, and all have working fireplaces. The separate Carriage House is a two-bedroom home away from home, complete with kitchen and private entrance. 

There are no more gambling tables at this exceedingly comfortable and welcoming place but wandering into the ground-floor’s Conservatory or Library, don’t be surprised to find a heated game of Scrabble going on, as guests sip wines chosen from the 24-hour wine self-dispenser nearby (a genius idea for a small hotel) or coffee from the always available automatic coffee machine. The Parlor Bar, with its massive portrait of a gorgeous woman, is also a natural gathering place for guests, as is the dining room/patio that overlooks the bay. 

Designed by owners Werton Bellamy and Kellye Walker to be a place of peaceful tranquility, the manor’s restaurant and bar are exclusive to guests only, as is the small private beach at water’s edge. It’s easy to while away the day here, forgetting the stresses of real life, or to get motivated and grab a bike for a ride or play a round of golf at the nearby 9-hole course.

No Eastern Shore getaway is complete without getting out on the water, so enlist the Manor’s helpful staff in booking charter fishing trips or sailboat, kayak or SUP rentals. Or simply head out the back door of the manor and take a swim in the Chesapeake Bay.

And if a weekend immersed in all things culinary is your idea of bliss, check out the “A Taste of Great Oak Manor,” their series of all-weekend immersions with renowned chefs from around the USA. From Japanese to Korean to Appalachian cuisine, their 2025 culinary weekends are led by James Beard honorees with a love of their craft.

CHESTERTOWN: GO FOR THE HISTORY, 
STAY FOR THE FESTIVALS
Great Oak Manor sits on the bay, about ten miles from Chestertown, the Kent County seat that’s a window into early American history and a thriving arts and culinary hotbed of creativity today. The locals love their annual festivals, too, and invite visitors to come and join the fun, either by car or boat, as the town sits on the Chester River, an easy sail from the Chesapeake Bay.

Start with the self-guided historical walking tour offered by the Historical Society of Kent County and see the beautiful Colonial Georgian-style homes built as this port town was formed in 1706, as well as the courthouse, old churches, taverns and other interesting buildings. There are also guided walking tours, nighttime guided ghost walks in October and the annual Dickens of a Christmas Holiday House Tour that gives a glimpse inside these lovingly kept 300-year-old homes.

Save time to wander in the arts district towards the river, where numerous studios and galleries welcome visitors and be sure to dine in one of Chestertown’s renowned eateries. Don’t miss Watershed Alley, which is actually down an alley off High Street, where Rodney and Lisa Scruggs have created a welcoming fine dining experience filled with flavors of the Bay Area, from seafood to locally grown produce, beautifully served up. Don’t miss the Eastern Shore Cream of Crab Soup with its delicious hint of curry and green apples.

And if festivals bring you joy, check the town’s calendar of annual events that draw people from all along the Eastern seaboard (and book in well ahead of time to Great Oak Manor on those weekends). May marks the famed Chestertown Tea Party Festival, a celebration and reenactment of the town’s own revolt against the British in 1774, plus a big parade, street party and more. Bring your Colonial costumes and you’ll fit right in.

September brings the annual Chestertown Jazz Festival and early November is the biggest fest of all, the Sultana Downrigging. That’s one of the largest gatherings of tall ships in North America, as ships, schooners and wooden boats converge on the port for a three-day celebration that includes a bluegrass festival as well. Buy tickets to get an unforgettable ride on one of the high-masted sailing ships (including the Sultana) and don’t be surprised to find lots of revelers dressed as pirates and sailors as the festivities unfold.

Great Oak Manor and Chestertown are about a three-hour drive from New York City, and you’ll need a car to get there, as there is no viable public transport to find your way to this very special part of Maryland’s Eastern Shore.

For more information about Great Oak Manor, go to greatoakmanor.com
For more information about Chestertown and the historical walking tour, go to
visitmaryland.org and kentcountyhistory.org