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 […]
Visit your favorite local food and artisan vendors on High Street to purchase delicious veggies, flowers, crafts and more!
Come see Main Street's new offices, watch us cut the giant ribbon, and peak at all of the new things at the Visitors Center! Food and drink will be served. Thursday, June 20 5:00pm 122 N. Cross Street
Visit your favorite local food and artisan vendors on High Street to purchase delicious veggies, flowers, crafts and more!
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 helping Main Street Chestertown develop a community-led plan for the Chestertown Historic District. Public Workshop Wednesday, June 26 5:30pm Chestertown Volunteer Fire House MORE INFO […]
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 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 […]
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 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 […]
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 weather. Kona Ice will be in Wilmer Park selling refreshments. Don't miss this holiday favorite!
On the first Friday of the month, downtown shops stay open until 8 pm and galleries stage opening and special events.
