Kent County Maryland Calendar of Events- October 2022


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October 1

Chestertown Car Show
  • Chestertown Car Show

  • Saturday,   |  2 p.m. to 6 p.m.
  • Location: Downtown Chestertown - High Street, Chestertown - Downtown Chestertown - High Street, Chestertown
  • Register your own pride and joy to compete for trophies, or just stroll the street to admire what other auto enthusiasts have brought to display, from custom hotrods to classic and antique beauties. C...

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October 8

  • Touch A Truck Ag Fest

  • Saturday,   |  10am - 2pm
  • Location: Kent County Ag Center - 21349 Tolchester Beach Rd, Chestertown, MD 21620
  • Come out to the Ag Center and explore emergency vehicles, construction and farm equipment, trucks and more! Fun Family Event!

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October 14

HP Fest
  • HP Fest

  • Friday,   |  All Day
  • This event runs October 14 to October 15
  • Location: Downtown Chestertown-Various - 200 Block of High Street
  • A Weekend of Magic:

    Grab your wand, hop on your broom, and come for a weekend of magic at the fifth annual Chestertown HP Festival. Explore our colonial river town and join us for spectacular activ...

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October 20

Cars on High
  • Cars on High

  • Thursday,   |  6pm-8pm
  • Location: 300 High Street - Fountain Park
  • Come on out to Cars On High St. in Chestertown, MD to show off your Exotic, Classic or Vintage car on the 3rd Thursday of the month, April thru October....

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October 22

5th Annual - Chestertown Rotary Soup & Sip
  • 5th Annual - Chestertown Rotary Soup & Sip

  • Saturday,   |  Noon - 3 pm
  • Location: The Kitchen at the Imperial - 208 High Street
  • Crab Soup Competition & Wine Tasting

    You be the judge of Kent County's best crab soup!

    Bring $ bills to vote at each booth.

    $25 includes a wine glass and raffle ticket.
    Proceeds thi...

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