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
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“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 StVisit your favorite local food and artisan vendors on High Street to purchase delicious veggies, flowers, crafts and more!
Visitor Center Ribbon Cutting & Open House
Visitors Center 122 N. Cross St, Chestertown, MD, United StatesCome 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
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!
Downtown Master Plan Public Workshop
Chestertown Volunteer Fire Company 211 Maple Ave, Chestertown, MD, United StatesCome 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 […]
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!
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!