iPhone Photography Weekend Workshop at Great Oak Manor

We like to advertise how photogenic our waterfront property is and now we’re inviting aspiring iPhone photographers to come out and take advantage of our beautiful views for an entire weekend event. On November 6th and 7th, we’re hosting an iPhone Photography Workshop under the tutelage of Karen Klinedinst. Karen Klinedinst is a landscape photographer and graphic … 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

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

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

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