Chestertown Maryland Calendar of Events- October 2024


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October 1

Brampton Inn Ship-To-Shore Experience with Chester River Packet Co.
  • Brampton Inn Ship-To-Shore Experience with Chester River Packet Co.

  • Tuesday,   |  6:00pm - 8:00pm
  • Location: Brampton Inn - 25227 Chestertown Rd
  • The Brampton Inn invites visitors to catch the sunset aboard the Chester River Packet, a 1920’s-style, touring yacht. This immersive experience allows guests to mingle and unwind on a serene two...

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  • God's Lioness: Carl Phillips on Sylvia Plath

  • Tuesday,   |  6:00PM
  • Location: Rose O'Neill Literary House - Enclosed Porch
  • Carl Phillips is the author of 17 books of poetry, most recently Scattered Snows, to the North (2024) and Then the War: And Selected Poems 2007-2020, which won the 2023 Pulitzer Prize. His other honor...

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October 2

  • Carl Phillips Reads From His Work

  • Wednesday,   |  6:00PM
  • Location: Rose O'Neill Literary House - Enclosed Porch
  • Carl Phillips is the author of 17 books of poetry, most recently Scattered Snows, to the North (2024) and Then the War: And Selected Poems 2007-2020, which won the 2023 Pulitzer Prize. His other honor...

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October 13

Chestertown Challenge Half Marathon & 5K Run/Walk
  • Chestertown Challenge Half Marathon & 5K Run/Walk

  • Sunday,   |  9:00am
  • Location: Wilmer Park - - Wilmer Park
  • Half Marathon & 5K Run/Walk to benefit KART, providing therapeutic horseback riding and equine activities for the special needs community.

    Both courses USAFT certified.

    Race day registrati...

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October 17

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

  • Thursday,   |  6:00 - 8:00 pm
  • Location: River Packet - High Street Town Dock
  • Ladies' Night on the Chester River! Gather your friends/family for a fun evening with food and drinks aboard the River Packet. Reservations are required - click the link for more information and ...

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Cars on High
  • Cars on High

  • Thursday,   |  6pm-8pm
  • Location: 300 Block of High Street
  • Come show off your favorite car or marvel at other people's pride and joy. This event does not require registration and is free and open to the public....

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October 23

  • So You Want to Make a Podcast? With Diannely Antigua

  • Wednesday,   |  6:00PM
  • Location: Rose O'Neill Literary House - Enclosed Porch
  • Diannely Antigua is a Dominican American poet and educator, born and raised in Massachusetts. She is the author of two poetry collections, Ugly Music (YesYes Books, 2019), and Good Monster (Copper Cny...

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October 24

  • A Reading with Diannely Antigua

  • Thursday,   |  6:00PM
  • Location: Rose O'Neill Literary House - Enclosed Porch
  • Diannely Antigua is a Dominican American poet and educator, born and raised in Massachusetts. She is the author of two poetry collections, Ugly Music (YesYes Books, 2019), and Good Monster (Copper Cny...

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October 27

Elegant Afternoon Tea at Brampton Inn
  • Elegant Afternoon Tea at Brampton Inn

  • Sunday,   |  2:00pm - 3:30pm
  • Location: Brampton Inn - 25227 Chestertown Rd, Chestertown MD 21620
  • Join us for an exquisite afternoon filled with charm and indulgence at Brampton Inn. Indulge in a delightful selection of finest teas and delectable treats that will transport you to a world of refine...

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