ENJOY CHESTERTOWN'S YEAR-ROUND
Events Calendar
Upcoming Events
Whether you're a local or a visitor, our event calendar is brimming with engaging activities that cater to diverse interests. From lively festivals and captivating performances to informative workshops and delightful markets, there's always something for everyone. We can't wait to welcome you! Mark your calendars and join us for an event soon.
Hosting An Event?
Hosting an event you want to advertise to locals and visitors? Use the button to submit your event listing. For questions about events, contact Main Street at office@mainstreetchestertown.org.
June 2026
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Your Guide to Chestertown
Latest News
A Day Trip to Chestertown for Culture, Cuisine & Cocktails
Chestertown, Maryland is the kind of Eastern Shore town that rewards a slow wander. Spend the day exploring coffee shops, bookstores, galleries, Chesapeake history, waterfront views, cocktails, oysters, and live theater.
Growing Toward the Future: Opportunities to Upgrade and Invest in Your Downtown Business
Chestertown’s downtown businesses have new opportunities to invest in their future. From Enterprise Zone tax incentives to Facade Improvement Grants, local business owners and property owners may be able to access funding and support for upgrades, renovations, and long-term growth.
Main Street Chestertown Earns National Accreditation For Excellence in Revitalization
Main Street Chestertown has once again been nationally accredited by Main Street America™ for excellence in downtown revitalization. This top-tier recognition celebrates local leadership, historic preservation, and sustainable community development in Chestertown’s historic district.