Main Street is currently seeking a new full-time Executive Director to begin immediately. For more information and to apply, click the button below
Come hear about the progress of the Downtown Master Plan and give feedback on preliminary concept designs. This workshop will be lead by Design Collective, a Maryland-based firm who is […]
Visit your favorite local food and artisan vendors on High Street to purchase delicious veggies, flowers, crafts and more!
JOIN US for the ShoreRivers SOLSTICE CELEBRATION You don’t want to miss this signature summer event. For a decade, ShoreRivers has hosted the Summer Solstice Celebration on the banks of […]
Join us for an Open House at Brampton 1860! Explore the historic charm of Brampton 1860 a boutique hotel and venue located at 25227 Chestertown Rd. This in-person event offers […]
Chestertown's Annual 4th of July Fireworks! Shot off from Wilmer Park, the fireworks can be enjoyed from many spots on land and water. Show will begin at approximately 9:15pm, depending […]
On the first Friday of the month, downtown shops stay open until 8 pm and galleries stage opening and special events.
Visit your favorite local food and artisan vendors on High Street to purchase delicious veggies, flowers, crafts and more!
Visit your favorite local food and artisan vendors on High Street to purchase delicious veggies, flowers, crafts and more!
Visit your favorite local food and artisan vendors on High Street to purchase delicious veggies, flowers, crafts and more!
Hosted by the Downtown Chestertown Association, Crazy Days is Chestertown’s annual sidewalk sale with businesses offering crazy deals and restaurants offering crazy specials.
