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!
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
Loading view.
Shore Rivers’ Solstice Celebration
Wilmer ParkJOIN 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 the Chester River. Enjoy live music and dancing, refreshing cocktails, delicious food, good company, and an exceptional live auction to benefit healthier local waterways. Tickets […]
Brampton 1860 Open House
Brampton 1860 25227 Chestertown Rd, Chestertown, MD, United StatesJoin 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 a unique opportunity to step back in time and experience the beauty of this iconic location. Discover the rich history behind Brampton 1860. Learn about […]
Free
Fireworks over the Chester River
Wilmer ParkChestertown'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 weather. Kona Ice will be in Wilmer Park selling refreshments. Don't miss this holiday favorite!
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!
Crazy Days
Hosted by the Downtown Chestertown Association, Crazy Days is Chestertown’s annual sidewalk sale with businesses offering crazy deals and restaurants offering crazy specials.
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!