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!
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 […]
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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!
Horizons of Kent and Queen Anne’s Dance with the Stars – A Gatsby Gala
Brittland Manor 211 Britland Farm Ln., Chestertown, M, United StatesSaturday, November 16, 2024 (6:00 PM - 11:00 PM) (EST) Description It’s back! The wait is over. Horizons of Kent and Queen Anne’s is excited to announce Dance with the Stars 2024. This year the theme is, “A Gatsby Gala,” and will take place on November 16, 2024, at Brittland Manor! This fundraiser is a […]