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

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!

National Music Festival

The National Music Festival transforms Kent County into a hub of music. The nationally recognized event will feature music to suit virtually every taste — from symphonies and chamber music to hints of jazz. More than 30 concerts and over 200 open rehearsals are scheduled throughout the festival in venues across the Eastern Shore.

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!

“Heroes of the Chesapeake” Juneteenth Celebration

Friday, June 14th, 2024, and Saturday, June 15th, 2024, the Bayside H.O.Y.A.S., will host their annual “Heroes of the Chesapeake” Juneteenth celebration at Fountain Park in Chestertown, Md. This two-day celebration will include live musical performances by Best Kept Soul and Sombarkin’. The two-day celebration will also include a living history performance by nationally recognized […]

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!