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

That’s the Spirit

Expect a memorable night at the Kitty Knight House with a fabulous 3 course meal specially prepared by celebrity chef Robbie Jester including wine pairings form Crow Vineyard for the appetizer and main courses. On the menu is: Spinach Salad, Roasted Pear, “Everything” Croutons, Feta Cheese, and Honey Vidalia Vinaigrette Choice of Braised Crow Farm […]

$161.90

Fall Art Walk

Come to the Chestertown Arts & Entertainment District’s ART WALK. Dozens of artists and artisans will be selling works at galleries, storefronts, restaurants and around town. Live music will also be happening throughout town.For information email hester@kentculture.org or call the Kent Cultural Alliance at 410-778-3700 April 20, 2024 September 14, 2024 December 14, 2024

Farmers’ & Artisans’ Market

High St & Cross St

Visit your favorite local food and artisan vendors on High Street to purchase delicious veggies, flowers, crafts and more!

Rivers of the Eastern Shore Book Talk

Emmanuel Episcopal Church Parish Hall 101 North Cross St., Chestertown, M, United States

Join ShoreRivers and the Historical Society of Kent County for an immersive journey into the history of Maryland's Eastern Shore, and how Kent County's rivers shape our way of life--then, now, and in the future. Karen Footner, granddaughter of the author, and Dennis Forney, Publisher Emeritus of the Cape Gazette in Lewes, Delaware will provide […]

Free
Event Series Cars on High

Cars on High

High St. High St., Chestertown, MD, United States

Every third Thursday, April through October, weather permitting. Owners share classic, antique, and custom cars on the 300 Block of High Street. No registration necessary.

Farmers’ & Artisans’ Market

High St & Cross St

Visit your favorite local food and artisan vendors on High Street to purchase delicious veggies, flowers, crafts and more!

Farmers’ & Artisans’ Market

High St & Cross St

Visit your favorite local food and artisan vendors on High Street to purchase delicious veggies, flowers, crafts and more!

Farmers’ & Artisans’ Market

High St & Cross St

Visit your favorite local food and artisan vendors on High Street to purchase delicious veggies, flowers, crafts and more!

Farmers’ & Artisans’ Market

High St & Cross St

Visit your favorite local food and artisan vendors on High Street to purchase delicious veggies, flowers, crafts and more!