First Friday
On the first Friday of the month, downtown shops stay open until 8 pm and galleries stage opening and special events.
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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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!
Annual Chestertown Jazz Festival
Wilmer Park28th Annual Chestertown Jazz Festival Presents Jazz by the River Saturday , September 7, 2024 | 12:00 PM - 6:00 PM Location: Wilmer Park - 413 S Cross Street Chestertown MD Contact: Garfield […]
Mini Chesapeake Film Festival
Garfield Center for the Arts 210 High Street, Chestertown, MD, United StatesThursday , September 12, 2024 | 4–6pm, 7–9pm Location: Garfield Center for the Arts - 210 High Street, Chestertown, MD, 21620 Contact: ShoreRivers Phone: 443.385.0511 Email: info@shorerivers.org URL: https://www.eventbrite.com/e/chesapeake-film-festival-presents-fragile-riversfertile-lands-tickets-906846471207 The Chesapeake Film Festival and ShoreRivers invite […]
That’s the Spirit
Expect a memorable night at the Kitty Knight House with a fabulous 3 course meal specially prepared by celebrity chef Robbie Jester including wine pairings form Crow Vineyard for the […]
$161.90
Fall Art Walk
Come to the Chestertown Arts & Entertainment District’s ART WALK. Dozens of artists and artisans will be selling works at galleries, storefronts, restaurants and around town. Live music will also be […]
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!
Rivers of the Eastern Shore Book Talk
Emmanuel Episcopal Church Parish Hall 101 North Cross St., Chestertown, M, United StatesJoin ShoreRivers and the Historical Society of Kent County for an immersive journey into the history of Maryland's Eastern Shore, and how Kent County's rivers shape our way of life--then, […]
Free
Cars on High
High St. High St., Chestertown, MD, United StatesEvery third Thursday, April through October, weather permitting. Owners share classic, antique, and custom cars on the 300 Block of High Street. No registration necessary.
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!