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

06/07/2026

A huge THANK YOU to everyone who came out to enjoy First Friday in Downtown Chestertown! ❤️

We loved seeing our streets filled with friends, families, visitors, and neighbors supporting our amazing downtown community. A special thank you to all of our incredible shops, restaurants, galleries, and businesses for staying open late and helping make the evening so special.

Your support of our local businesses means so much and helps keep our downtown vibrant and thriving. We hope you had a wonderful evening, and we can’t wait to see you again next month for another fantastic First Friday!

06/05/2026
06/05/2026
06/05/2026

Dont forget to swing by KidSPOT on First Friday for some wholesome fun for the whole family. It’s going to be a great evening in Chestertown!

06/05/2026
06/05/2026
06/02/2026

Join us TONIGHT for Swing Night, our special opening concert for Season 14! Tickets are available at nationalmusic.us, at Headquarters until 2pm, or at the door.

See you tonight!

06/02/2026
☀️ June First Friday – Summer Starts Here! ☀️Join us in Downtown Chestertown on Friday, June 6 from 5PM–8PM for an eveni...
06/02/2026

☀️ June First Friday – Summer Starts Here! ☀️

Join us in Downtown Chestertown on Friday, June 6 from 5PM–8PM for an evening of music, food, shopping, and family fun as we kick off summer together!

🎶 Live Music by Stacy Bines
Enjoy hits from the 60s to today featuring rock ’n roll, classic hits, pop favorites, and something for everyone!

🍔 Delicious Food by Rick’s Rollin’ Restaurant
Great food • Local flavor • Good vibes!

🎵 Celebrate National Music Festival
Enjoy the joy of music all throughout downtown with special performances during the evening.

🎨 Kidspot at First Friday
Bring the kids for fun activities, crafts, games, and something for every child to enjoy!

🛍️ Shop • 🍽️ Dine • 🎶 Listen • 🚶 Explore

Gather your family and friends and come experience everything downtown has to offer. Good music, great food, community fun — summer starts here!

📍 Downtown Chestertown
📅 Friday, June 6
⏰ 5PM–8PM

05/31/2026

Address

Chestertown, MD
21620

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