The Fowl Life, Outdoor Channel, Eastern Shore Hunting

Great Oak Manor will appear on an upcoming episode of The Fowl Life showcasing Eastern Shore Hunting on the Outdoor Channel! Towards the end of the month of January, Great Oak Manor had the pleasure of hosting the cast and crew of The Fowl Life, which included the show’s host Chad Belding, as well as … Read More

Chesapeake Wine Trail on Maryland’s Eastern Shore

Not only does Maryland’s Eastern Shore offer an abundance of fresh seafood, beaches, wildlife and history, we also have a tantalizing wine trail…and Great Oak Manor is right in the middle of it. What better way to experience the beauty of the Chesapeake Bay area than with wine? Surprisingly enough, the sandy and well-drained soil … Read More

Pirates Invade Rock Hall On August 7-9, 2015

Ahoy, me hearties! Tis time for all able seamen to heave to and make for thar Great Oak Manor’s fair haven and her shipshape cabins to prepare for the Annual Pirates and Wenches Fantasy Weekend! This event has been on the books for seven years already with no signs of belay. Translation: Hello friends! Great … Read More

Chestertown Live Theater: Garfield Center for the Arts

The summer vacation season is in full swing and we welcome guests to our beautiful bayside inn during these warm months! And while it’s easy to immerse yourself in the bay and sea activities in the area, MD isn’t all about the bay and the sea; there are plenty of cultural activities available to our … Read More

Paddling Near Chestertown: a Water-Lover’s Delight

Whether you are into kayaking, canoeing or even floating on an inner-tube, the area surrounding Chestertown has a variety of waterways you’re sure to enjoy. When you stay at Great Oak Manor, you can access the Chesapeake Bay right from our property. In fact, we even have a canoe and kayaks for our guests’ use! … Read More