An Eastern Shore Murder Mystery Event: 1950s Italian Wedding Style

While not as old as everyone first thinks, our 18th century-style manor has definitely observed a lot throughout its years. In fact, we field questions all the time about whether the house is haunted or even if we ever feel like we’re living a live-action version of “The Shining” (That answer for me? Yes, especially … 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

The Chestertown Kent County Fair, July 2015

It will be here before you know it! Chestertown’s own Kent County Fair comes to town this July 16, 17 and 18, 2015! Just like most county fairs in the USA, you’ll find lots of food, livestock, exhibits, rides, music, and much, much more! Watch in amazement as the brave take on the bull, laugh … Read More

Chestertown Independence Day Events and Activities

Planning to come to Chestertown over the Independence Day holiday? You won’t be disappointed in the events happening this entire week! From the very start of the month through the entire July 4, 2015 weekend, Chestertown is jam-packed with fun activities for the whole family! Thursday, July 2 (and before): The Wheelmen come to Chestertown … 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

Riverfront Concert Series: Summer Music in Chestertown

Kent County comes alive with music during the summer. We would like to take this month to highlight some of the exciting upcoming musical events in the area. June and July find the Riverfront Concert Series coming to the shores of the Chester River. Held at the Custom House Lawn: 101 South Water Street, Chestertown, … 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