Downtown Chestertown Association

Downtown Chestertown Association Historic Downtown Chestertown on Maryland's Eastern Shore: where art, history and nature meet.

Dedicated to promoting businesses and services in Chestertown, as well as hosting events and activities to increase tourism and encourage residents to shop locally

05/31/2026
05/25/2026

🇺🇸 The Downtown Chestertown Association wishes you a safe and meaningful Memorial Day.

Today, we honor and remember the brave men and women who made the ultimate sacrifice in service to our country. As we gather with family and friends, we pause to reflect on their courage, sacrifice, and dedication to protecting the freedoms we cherish every day.

May we never forget those who gave all for our nation. ❤️🤍💙

05/22/2026
05/22/2026
05/22/2026
05/22/2026

One of our two biggest weekends of the entire year - alongside Downrigging in the fall - is finally here, and we are so excited to welcome all of you to Chestertown this weekend.

We’re trying not to obsess over the weather forecast just yet 😅 and are hoping things shift in our favor, but rain or shine, we’ll be here all weekend with scratch-made food, sourdough pastries, coffee, cocktails, and our outdoor patio bar ready to go.

Whether you’re visiting town for the festivities or you’re one of our amazing locals, we hope you’ll stop by and celebrate with us!

05/22/2026

Be ready to honor the military personnel who died while serving in the Armed Forces.
Wear your shirt, belt, hat, and even socks with pride; making a statement you appreciate their service.
We love that the parade passes right in front of the store... Saturday at 10:30am!
Jerry Moe's is open 7 days a week. We look forward to seeing you.
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Chestertown, MD
21620

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