Kent County Maryland Calendar of Events- September 2025
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September 4
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Hillary Gardner
- Thursday, | 8:00pm
- Location: The Mainstay - 5753 N MAIN STREET ROCK HALL, MD 21661 - The Mainstay - 5753 N MAIN STREET ROCK HALL, MD 21661
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The Mainstay in Rock Hall ushers in the Chestertown Jazz
Festival with NYC-based Songbook stylist/ jazz vocalist Hilary
Gardner in her fourth return visit.
Hilary “evokes memories of anothe...
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September 5
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Cookie Chronicles Book Party
- Friday, | 5pm
- Location: The Bookplate - 112 S. Cross Street
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Drop by The Bookplate during First Friday in September for a celebration of Robbi Behr & Matthew Swanson's latest installment in the Cookie Chronicles; "Ben Yokoyama & The Cookie of ...
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Opening Reception: Hispanic Heritage Month Exhibition Featuring Ortiz & Granillo
- Friday, | 5-7pm
- Location: RiverArts Community Arts Center - 343 High Street
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In celebration of Hispanic Heritage Month, RiverArts is proud to present an exhibition honoring the artistry of two master makers whose work blends tradition, craftsmanship, and cultural heritage, Bob...
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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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Seventh Annual Charlie Joiner Memorial Decoy Show
- Saturday, | 9:00 a.m. - 3:00 p.m.
- Location: Galena Volunteer Fire Company - 90 E. Cross Street, Galena, MD 21635
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Join us for the Seventh Annual Charlie Joiner Memorial Decoy Show. Featuring: Decoys, fishing lures, shell boxes, fishing and hunting licenses, oyster cans and much more!
Proceeds benefit "C...
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Stop the Bleed
- Saturday, | 1pm
- Location: Kent County Public Library - Chestertown Branch - 408 High Street, Chestertown
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In an emergency situation, being able to act quickly can mean the difference between life and death. This workshop will teach you the skills you need to recognize and control life-threatening bleeding...
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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 12
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Artist Panel: Hispanic Heritage Month Exhibition Featuring Ortiz & Granillo
- Friday, | 5-7pm
- Location: RiverArts Community Arts Center - 343 High Street
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Celebrate Hispanic Heritage Month with RiverArts at an exhibition spotlighting master makers Bob (Roberto) Ortiz and Fredy Granillo. Ortiz crafts elegant furniture blending tradition, design, and func...
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September 13
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Second Saturday Market
- Saturday, | 10:00 AM - 2:00 PM
- Location: St. Dennis Catholic Church - 156 N. Main Street
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The Second Saturday Market returns to downtown Galena on Saturday, September 13, 2025. This family-friendly outdoor event features a wide range of artisan vendors, small businesses, and local entrepre...
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Movie Night - Inside Out 1
- Saturday, | 7:00 PM
- Location: Galena Community Park - 105 Sycamore Lane
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🎬✨ Movie Night is BACK! ✨ðŸ¿
We had such a great time last year, we’re bringing it back! 🙌 Join us Friday, September 13 at 7:00 PM for an under the stars showing o...
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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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Locally Grown Dinner with Chef Robbie Jester & Chef Jesse Townshend
- Thursday, | 6:30 PM
- Location: Deep Blue at Kitty Knight - 14028 Augustine Herman Highway Galena MD 21635
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Join us for a special four-course dinner paired with Crow Vineyard wines that celebrates the best of the season with chef Robbie Jester and special guest chef, Jesse Townshend.
Tickets $85 (inclu...
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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 26
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Cruise In Car Show
- Friday, | 4 pm-8pm
- Location: Cruise In Car Show - Rock Hall Yacht Club 22795 McKinleyville rd
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Cruise In Car show at the Rock Hall Yacht Club
Free to All
Come show your classic or cool cars or come and enjoy these beauties showcased along the scenic Chester River.
The club will be open servi...
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Maryland Outdoors Festival
- Friday, | All Day
- This event runs September 26 to September 28
- Location: Molly's Place Sporting Goods - 12503 Augustine Herman Hwy, Kennedyville, MD 21645
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Join hundreds of outdoor enthusiasts at Molly’s Place in Kennedyville, Maryland for the Maryland Outdoors Festival, running Friday through Sunday, September 26‑28! Celebrate hunting...
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Verny Varela Performance
- Friday, | 7pm
- Location: RiverArts Community Arts Center - 343 High Street
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Join us for an unforgettable evening of music, culture, and community as internationally acclaimed Colombian singer, composer, and bandleader Verny Varela takes the stage.
With roots in salsa, Lati...
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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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