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!

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!

Shore Love Quilting Show & Market

Presbyterian Church of Chestertown 905 Gateway Drive, Chestertown, MD, United States

Put on by the Old Kent Quilters Guild Admission by Donation ($8 for 2 days, max $24 per family, Kids 12 and under free) Scissor sharpening Friday only.    

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!

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 High Street.