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

08/07/2026
08/07/2026
08/07/2026

Iconic Old Bay, Baltimore born, defines Maryland culinary culture. Created in 1939, it has been a staple of the Chesapeake region for over 85 years. Come see our collection and choose from great logo items: Beach towels, puzzles, mugs, glassware, hats, t's, socks and more.

We are open today until 5 pm.
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08/07/2026
08/07/2026

Historic charm, peaceful countryside and the welcoming waterfront town of Chestertown come together to make Brampton 1860 a memorable Eastern Shore escape. Owner, Hilari Rinehart shares how the historic inn blends timeless character with modern comforts while highlighting the best ways to experien

08/07/2026
08/07/2026

Happy 1st Friday Chestertown! Just in, lots of new Local Boy tees, sweatshirts, and jackets right here at Jerry Moe's! Stop in today, we are open until 8pm, 930am to 5pm Saturday, and 11am to 4pm Sunday! Follow us on Facebook!

08/07/2026

🍽️ TONIGHT! The Common Table opens at RiverArts! 🎨

Join us tonight, Friday, August 7, from 5–7 PM for the opening reception of The Common Table, an exhibition exploring the connections that bring us together.

Inspired by the timeless tradition of sharing a meal, the exhibition explores the many meanings of the “common table”—from family dinners and community gatherings to unexpected moments of connection found throughout nature. Through a variety of artistic mediums, participating artists share their interpretations of companionship, hospitality, belonging, and shared experiences.

✨ Tonight’s celebration includes:
🎨 Artwork by participating artists
🍴 A tasting of delicious appetizers generously provided by local restaurants, including Evergrain Bread Company, Cafe Sado, The Kitchen at the Imperial, Phat Daddy’s, Bad Alfred’s, China House, with more to come!
🤝 An opportunity to meet the artists and connect with our community
💛 The launch of an important fundraising campaign supporting RiverArts’ vision for a future standalone gallery space

đź“… Friday, August 7
🕔 5–7 PM
đź“Ť RiverArts Gallery, 343 High Street, Chestertown

Come gather around The Common Table with us tonight. We’d love to celebrate with you!

08/07/2026

🎉 IT’S FIRST FRIDAY IN DOWNTOWN CHESTERTOWN! 🎉

Make plans to come downtown tonight and enjoy First Friday! 🛍️✨

Our local shops are staying open late, giving you extra time to shop, browse, and support the wonderful businesses that make Downtown Chestertown so special. ❤️

And while you’re here, stop in and enjoy dinner, drinks, or a sweet treat at one of our local restaurants! 🍽️🍷

Come stroll the streets, shop local, dine local, and enjoy a great evening in Downtown Chestertown!

Support local. Shop local. Dine local. ❤️

The Downtown Chestertown Association thanks you for helping keep our downtown community thriving!

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Chestertown, MD
21620

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