Chestertown Maryland Calendar of Events- November 2025


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November 20

Girls' Night Out on the River Packet
  • Girls' Night Out on the River Packet

  • Thursday,   |  5:00 - 7:00 pm
  • Location: River Packet - High Street Town Dock
  • The FINAL Ladies' Night of the 2025 Season 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...

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November 29

Chestertown A&E Holiday Art Walk
  • Chestertown A&E Holiday Art Walk

  • Saturday,   |  9:00 am to 3:00 pm
  • Location: Chestertown A&E District - Downtown Chestertown
  • 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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