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

Eastern Shore Wedding: Behind the Scenes

It’s no secret how much planning a wedding takes over the daily lives of a couple. We know from family stories and pop-culture about the stressful moments, the tears, and the hair-pulling frustration over the little details that seem as though they will never be figured out. Choosing a venue is half the battle for a couple and … Read More

Chestertown MD Events Happening on May 22-25

Thinking of a visit to lovely Chestertown, MD this weekend? You’ve certainly picked a great weekend to join us, as there are two big draws! First, we have the Chestertown Tea Party Festival: a local tradition steeped in history and mixed with a street-fair vibe. Second, this weekend kicks off the Schooner SULTANA Public Sails … Read More

May & June 2015 Events: National Music Festival

Monteverdi, Haydn, Bernstein, Glenn Miller, Duke Ellington, Benny Goodman, Brahms, Beethoven, Schubert… you’ll hear works from all these composers and more between May 31, 2015 and June 13, 2015 when Chestertown’s Washington College hosts the 2015 National Music Festival. The National Music Festival was founded by Conductor and Artistic Director Richard Rosenburg and Executive Director … Read More

Join Us for 2015 Washington College Commencement

Get ready: Washington College’s 232nd Commencement is imminent, and graduates are ready to make their marks on the world! Yes, after four (or five, or six… or more) hard years, both undergraduate and post-graduate students receive their well-earned degrees on May 16, 2015.  We encourage proud parents & families to reserve their room(s) early for … Read More

Chestertown First Fridays Deliver Art & Entertainment

Are you planning your bed and breakfast getaway at Great Oak Manor over a first-weekend-of-the-month? Then you’re in for a treat! No matter what time of year it is, the town of Chestertown, its shopkeepers and its residents celebrate First Friday each month! And what is a “First Friday”? It is an occasion that welcomes … Read More