Cars on High
High St. High St., Chestertown, MD, United StatesEvery third Thursday, April through October, weather permitting. Owners share classic, antique, and custom cars on the 300 Block of High Street. No registration necessary.
Main Street Chestertown is Hiring!
Main Street is currently seeking a new full-time Executive Director to begin immediately. For more information and to apply, click the button below
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Farmers’ & Artisans’ Market
High St & Cross StVisit your favorite local food and artisan vendors on High Street to purchase delicious veggies, flowers, crafts and more!
RiverArts Studio Tour
RiverArts 315 High Street, Suite 106, Chestertown, United StatesEver wonder what an artist's studio really looks like? Curious about how artists bring their incredible work to life? Or perhaps you’re eager to take home a piece of original art? The Chestertown RiverArts Annual Studio Tour offers you the perfect opportunity to step inside the creative spaces of Kent and Upper Queen Anne's Counties. […]
Free
Farmers’ & Artisans’ Market
High St & Cross StVisit your favorite local food and artisan vendors on High Street to purchase delicious veggies, flowers, crafts and more!
Downrigging
Now in its 24rd year, the Sultana Education Foundation’s Downrigging Weekend Festival is one of the largest annual tall ship gatherings in North America. The festival features a long-weekend of Tall Ship sails, tours, incredible live bluegrass music, lectures, exhibits, family activities, regional food and more. Proceeds benefit the Foundation’s environmental literacy programs and the other nonprofits […]
Featured
Downrigging Weekend
The Sultana Education Foundation's Downrigging Weekend highlights Tall Ships and Bluegrass, along with nautical history and Chesapeake Bay ecology.
First Friday
On the first Friday of the month, downtown shops stay open until 8 pm and galleries stage opening and special events.
Farmers’ & Artisans’ Market
High St & Cross StVisit your favorite local food and artisan vendors on High Street to purchase delicious veggies, flowers, crafts and more!
Farmers’ & Artisans’ Market
High St & Cross StVisit your favorite local food and artisan vendors on High Street to purchase delicious veggies, flowers, crafts and more!
Farmers’ & Artisans’ Market
High St & Cross StVisit your favorite local food and artisan vendors on High Street to purchase delicious veggies, flowers, crafts and more!