What’s Happening: Downtown!

What’s Happening: Downtown!

Kent County’s Live Stream Events: What’s Happening


Kent County is always bursting with festivals, events, and other activities and we love a parade. Want to plan your calendar? Check out our always-updating feed for what might bring you to town again and again.

  • CANCELLED – Chestertown HP Festival

    Terrible news friends! We have just received a proclamation from the minister’s office that all festivities scheduled for the 2020 Chestertown HP Festival Weekend have been hereby canceled! All wizards and wizarding friends are encouraged to subscribe to the Chestertown HP Festival mailing list to receive any notices as they become available. Fear not! The… Continue Reading CANCELLED – Chestertown HP Festival

  • SUSPENDED – Saturday Mornings at KidSPOT!

    We’re busy at KidSPOT distributing craft bags to help kids in less affluent parts of our community have access to art materials and projects until we can open again. If you’re interested in supporting this initiative, please visit our website at https://chestertownriverarts.org/kidspot/ and make a donation. Thank you!

  • Chestertown Farmers Market – return to Fountain Park!

    UPDATE 6/29/2020 – The Chestertown Farmers’ Market will move back to the heart of downtown Chestertown starting Saturday, July 4, from 8 am to noon. Please come out and support the Farm and Artisan vendors. To meet pandemic safety standards, sections of the 200 and 300 blocks of High Street will be closed to traffic,… Continue Reading Chestertown Farmers Market – return to Fountain Park!

Chestertown’s Farmers Market Is Back In Business

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Chestertown’s Farmers Market is both a destination market that draws folks from all over and also a very community-spirited occasion. Totally focused on “local,” you can buy seasonal goods ranging from fruits, vegetables and meats to fresh flowers, soaps, and artfully created artisan works. See you next Saturday? Click here for additional info!

Calling All Cars: Come on Down to Cars on High

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Every third Thursday, from April through October, 6 to 8 pm, weather permitting. The schedule for 2020 tentatively includes April 16, May 14, June 18, July 16, August 20, September 17, and October 15.

Auto enthusiasts meet to share their classic, antique, and exotic wheels with the public.  Click here for additional info!

Calendar: Downrigging Weekend October 30 – November 1


The 19th Annual Downrigging Weekend will take place November 1 – 3. Organized by Chestertown’s own Sultana Education Foundation, this tall ship and wood boat festival is a cherished experience. Events include tall ship tours and sailing expeditions, enrichment lectures, musical concerts, 5K races and fireworks.

Click here for additional info!

Welcome Spring with an afternoon of music, food and fun in Fountain Park. Following Chestertown’s Earth Day celebration, the fun continues with food by Phat Daddy’s Barbeque, and Music by The Dirty Grass Players. Fun for the whole family!




Calendar: Chestertown Tea Party Festival May 22 – 24

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Can you believe this year marks the 44th annual Chestertown Tea Party Festival? The weekend, chock full of events surrounds the main event: A re-enactment of tossing tea overboard to support the Boston Tea Party. As well, don’t miss the parade, juried crafts stands, food trucks, music and more!

Click here for additional info!