Chestertown Maryland Calendar of Events- September 2025
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September 6
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Chestertown A&E Fall Art Walk
- Saturday, | 9:00 am to 3:00 pm
- Location: Chestertown A&E District - Downtown Chestertown
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Come to the Chestertown Arts & Entertainment District’s ART WALK. Dozens of artists and artisans will be selling works at galleries, storefronts, at a Pop-Up Gallery. Live music will also be...
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September 7
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Grape Stomp
- Sunday, | 12-4 PM
- Location: Crow Vineyard & Winery - 12441 Vansants Corner Rd. Kennedyville, MD 21645
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Join us in celebrating our 2025 Harvest with a Grape Stomp! Slip off your shoes, step in the barrel and get to stomping. Sip on a glass of wine, or a tasting of 3 wines while you learn about the diffe...
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Brampton 1860 Open House
- Sunday, | 12:00pm - 3:00pm
- Location: Brampton 1860 - 25227 Chestertown Rd, Chestertown MD 21620 - Brampton 1860 - 25227 Chestertown Rd, Chestertown MD 21620
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Explore the historic charm of Brampton 1860 a boutique hotel. This is a unique opportunity to experience the beauty of this iconic location. Discover its rich history. Learn about the events held on p...
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September 10
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WC-ALL Learn@Lunch - Ken Kozel
- Wednesday, | 12-1:30pm
- Location: Hodson Hall - Hynson Lounge - Washington College
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Join us for a catered Learn@Lunch with Kenneth Kozel, President and CEO of UM Shore Regional Health. With an extensive background in healthcare leadership—including roles at Upper Chesapeake Hea...
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September 18
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Girls' Night Out on the River Packet
- Thursday, | 6:00 - 8:00 pm
- Location: River Packet - High Street Town Dock
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Ladies' Night on the Chester River! Grab your friends/family for a fun evening with food and drinks on the River Packet. Reservations are required ahead of the cruise. Click the link for more inf...
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September 21
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Grape Stomp
- Sunday, | 12-4 PM
- Location: Crow Vineyard & Winery - 12441 Vansants Corner Rd. Kennedyville, MD 21645
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Join us in celebrating our 2025 Harvest with a Grape Stomp! Slip off your shoes, step in the barrel and get to stomping. Sip on a glass of wine, or a tasting of 3 wines while you learn about the diffe...
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September 23
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Literary House Series Presents: Wiley Cash
- Tuesday, | 6pm
- Location: Rose O'Neill Literary House - Rose O'Neill Literary House
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Wiley reads from his works. Wiley Cash is an award-winning and New York Times bestselling author of four novels. He has published widely on issues ranging from the environment to music, and he is the ...
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September 28
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Elegant Afternoon Tea at Brampton 1860
- Sunday, | 2:00pm - 3:30pm
- Location: Brampton 1860 - 25227 Chestertown Rd, Chestertown MD 21620
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Join us for an exquisite afternoon filled with charm and indulgence at Brampton 1860. Indulge in a delightful selection of the finest teas and delectable treats that will transport you to a world of r...
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