Chestertown Maryland Calendar of Events- October 2025
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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 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 25
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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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