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Upcoming Events at Great Oak Manor and in Kent County:

Ghost Walks – October 7, 14, 21, 28
Behold true tales of murder and mayhem; and folklore that still lingers from the region’s British and African heritage.

301 Devil’s Playground – October 13-14, 20-21, 27-28
301 Devil’s Playground is Maryland newest Haunted Attraction!! It has 3 Terrifying haunts that include The House of Hell , The Barn of Torture and The Zombie Paintball Ride .

Rock Hall Fest – October 14
The 20th annual Rock Hall fest will feature: music, crafts, kid’s activities, oysters and more food!

Osprey Triathlon – October 15
A family-friendly, USTA sanctioned race with entertainment and food at the finish!

Bloodshed, 27 Athletes, & a Quest for Northern Freedom, A Talk by Wil Haygood – October 18
Wil Haygood is a cultural historian and an award-winning author of seven nonfiction books. His latest book, Showdown: Thurgood Marshall and the Supreme Court Nomination that Changed America, was awarded the 2016 Scribe Book Award from the American Society of Legal Writers. Haygood’s 2008 Washington Post story about White House butler Eugene Allen, who served under eight presidents, won multiple journalism awards and was adapted into the prizewinning major motion picture The Butler directed by Lee Daniels.

An Elsworthy Evening: Orchard Point Oyster Sail – October 20
Spend the evening on the Skipkjack Ellsworth, with Scott Budden, as he shucks his Orchard Point Oysters, grown in our very own Chester River. Sail the river while listening to the musical stylings of James Stankowitz.

Sultana Downrigging – October 27-29
Come visit Chestertown – one of America’s best preserved historic seaports – to enjoy one of the largest annual Tall Ship gatherings on the East Coast. Visitors can expect to see a waterfront packed with ships, schooners, and wooden boats; performances by world-class musicians; lectures by nationally recognized authors and filmmakers; and plenty of opportunities to go sailing as part of a fleet of “Tall Ships!”

Dock Dogs at Kingstown Farm, Home and Garden – October 28
Dock Dogs is the world’s premiere canine aquatics competition. Come watch the dogs as they compete in a variety of categories to see who can jump furthest. You can even register and compete with your own dog! 

Chestertown’s Annual Halloween Parade – October 28
The parade will make its way down High Street. See all the creative costumes and enjoy this annual community event. 

Literary House Series: Under Your Spell—The Psychology of Witches: A Tea and Talk with Dr. Cri – October 31
Enjoy Halloween and learn a little about witches and vampires! Dr. Cristina Casado Presa  teaches courses at Washington College on contemporary literature of Spain; representations of the Spanish Civil War; female writers after Franco’s death; contemporary Spanish theater, and witches, ghosts, and vampires. She is an expert in twentieth and twenty-first century literature and culture of Spain, and focuses her research on women writers and representations of witchcraft in literature and culture.

Thanksgiving Dinner at Great Oak Manor – November 23
Start the day with a complimentary Eastern Shore Bloody Mary and enjoy wine with dinner. Reservations must be made no later than November 19. 

Christmas Dinner at Great Oak Manor – December 25
Enjoy complimentary Cranberry Wine Spritzers before a sumptuous Christmas dinner! Reservations must be made no later than December 21.

Call now to book your wonderful getaway in Kent County, MD!

Host Your Special Event at Our Manor on the Chesapeake Bay

It’s no doubt that Great Oak Manor is the perfect setting for a panoramic Eastern Shore wedding, but our slice of the Chesapeake is the ideal venue for any event you might be planning. Consider booking a family reunion, hunting party, yoga retreat, murder mystery party, or a dinner party. We even host corporate events as there are plenty of rooms and spaces for meetings. No matter what you’re planning, you’ll want it to be extraordinary, so why not choose a location that will be equally as memorable? Send an email to  for more information.