Kent County Maryland Calendar of Events- October 2025
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October 11
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Rock Hall FallFest
- Saturday, | 10am-4pm
- Location: Town of Rock Hall - Main Street Rock Hall
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FallFest attracts thousands of visitors from across the eastern seaboard showcasing the quaint hamlet of Rock Hall as we celebrate our heritage as a waterman’s town. Locals and visitors alike at...
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October 12
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Chestertown Challenge Half Marathon & 5K Run/Walk
- Sunday, | 9:00am
- Location: Wilmer Park - - Wilmer Park
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Half Marathon & 5K Run/Walk to benefit KART, providing therapeutic horseback riding and equine activities for children and adults with disabilities.
Both courses USATF certified.
Race day ...
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October 15
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WC-ALL Learn@Lunch - Mold, Myths & Methods: Real Stories from the Field
- Wednesday, | 12-1:30pm
- Location: Hodson Hall - Hynson Lounge - Washington College
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Join retired environmental scientist Larry Vetter for a catered Learn@Lunch on the science and stories behind mold remediation. With 30+ years of experience in hazardous spill response and indoor air ...
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October 16
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Girls' Night Out on the River Packet
- Thursday, | 5:00 - 7:00 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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October 18
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Studio Tour Weekend 1
- Saturday, | 10am-5pm
- This event runs October 18 to October 19
- Location: Various - - 343 High Street
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For those of you who would love the chance to chat with artists about their inspirations and see how they actually create their amazing work choose from 60 artists on the Chestertown RiverArts self-gu...
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October 24
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Witches of Rock Hall - Friday Evening
- Friday, | 5-8pm
- Location: Haven Harbour South - 21144 Green Lane
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Join us at Haven Harbour South to kick off the 6th annual Witches of Rock Hall Weekend. Bring friends and come dressed in your witchy finery! There will be music, fire pits, themed drinks, and more! W...
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October 25
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Witches of Rock Hall - Saturday
- Saturday, | 11am - 4:30pm
- Location: Town of Rock Hall - Ferry Park Beach and Main Street Rock Hall
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Witches of Rock Hall weekend. Dancing, games, shopping, food, drinks and lots of witchy fun!!
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Studio Tour Weekend 2
- Saturday, | 10am-5pm
- This event runs October 25 to October 26
- Location: Various - 343 High Street
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For those of you who would love the chance to chat with artists about their inspirations and see how they actually create their amazing work choose from 60 artists on the Chestertown RiverArts self-gu...
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October 26
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Resonance Concert: Ayreheart
- Sunday, | 3:00pm
- Location: St. Paul's, Kent (Parish Hall) - 7579 Sandy Bottom Road
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Ayreheart returns to the National Music Festival's Resonance Concert Series with a great program of Renaissance and contemporary music.
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