Getting ready for Fall Festival Season!


Summer lasts roughly 14 weeks:  June 20 to September 21.  So why is it that when August rolls around, and it’s quite literally the middle of the summer, everyone starts acting like summer is over and it’s all about back to school and Halloween decorations??  Slow it down, people.   Life is short, live in the moment, be in the now.  And then, when you’re done with that, check out the slew of festivals that are lined up for this fall!

September 8 through 11:  Chestertown Jazz Festival

The resurgence of the Jazz Festival has been a great boon to Chestertown, bringing amazing musical acts to our back yard.  This year they have nick-named it Four by Four:  4 days of music in 4 different venues around Kent County.  It just gets bigger and better each year!

September 24:  River Fest

Art, the environment and community converge for this family friendly afternoon festival.  Three words that sum it up:  Cardboard Boat Race!!!

September 30 & October 1:  Harry Potter Festival

You’ve been warned.  Wizards take over Chestertown for the 3rd year in a row.

October 1:  Historic House Tour

Always popular, the 46th (!!!) house tour put on by the Historical Society does happen to coincide with Harry Potter weekend.  (If you go to the website, the dates listed are wrong.  It is not the 21st & 22nd).    Yes, this means you will have to choose between wizards and wainscotting.

October 8:  Rock Hall Fall Fest

What three words describe this event?  Oysters, oysters, oysters.  There’s also music and parades…

October 22/23 & 29/30:  RiverArts Studio Tour

ALWAYS a favorite, this is an opportunity to see artists and artisans in their element, and perhaps purchase something for yourself or a loved one.  Unique gifts as local as you can get.

Never let it be said that there’s nothing to do in Chestertown.  Especially in the fall. Join us at our Maryland bed and breakfast and enjoy all that fall in Chestertown has to offer!

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