Arts and Entertainment

Kent County Maryland Calendar of Events- December 2019

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December 1

  • Annie: The Musical

  • Sunday,   |  8 PM Friday and Saturday 2 PM Sunday
  • This event runs November 29 to December 15
  • Location: The Garfield Center for the Arts at the Prince Theatre - 210 High Street
  • Directed by Jennifer Kafka Smith
    With equal measures of pluck and positivity, little orphan Annie charms everyone’s hearts despite a next-to-nothing start in 1930s New York City. She is determi...

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December 6

December First Friday
  • December First Friday

  • Friday,   |  5:00 p.m. - 8:00 p.m.
  • Location: Downtown Chestertown - Park Row, High Street, Cross Street, & Cannon Street
  • First Friday is a free event sponsored by Chestertown's downtown merchants, community organizations, and art galleries along Park Row, High Street, Cross Street, and Cannon Street. This event is ...

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Dickens of a Christmas
  • Dickens of a Christmas

  • Friday,   |  5 to 9 p.m.
  • Location: Chestertown Historic District - Downtown Chestertown, 300 block of High Street
  • The third annual Dickens of a Christmas weekend kicks off during First Friday festivities throughout the Historic District, bringing carriage rides, hot beverages, fire pits, s'mores stations, an...

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December 7

Dickens of a Christmas
  • Dickens of a Christmas

  • Saturday,   |  Noon to 9:00 p.m.
  • Location: Historic District, Chestertown - Downtown Chestertown
  • Chestertown's historic downtown fills with Dickensian fun that includes carriage rides, costumed street performers, high tea, live music, fire dancers, a holiday house tour, authentic British-the...

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Dickens Holiday House Tour
  • Dickens Holiday House Tour

  • Saturday,   |  10 a.m. to 2 p.m.
  • Location: Chestertown Historic District - Downtown Chestertown
  • Eight of Chestertown's finest historic homes, dressed for the holidays, welcome you with friendly docents and live music. Part of Main Street Chestertown's Dickens of a Christmas weekend, th...

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December 8

"Run Like the Dickens" 5K Run/Walk
  • "Run Like the Dickens" 5K Run/Walk

  • Sunday,   |  8 a.m.
  • Location: Downtown Historic Chestertown - 200 block of High Street
  • Good spirits prevail and costumes are welcome as participants walk or sprint their way on an in-town course that includes Chestertown's main commercial street, a loop through the beautiful Cheste...

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December 14

Second Saturdays in Chestertown
  • Second Saturdays in Chestertown

  • Saturday,   |  3 p.m. - 7 p.m.
  • Location: Bad Alfred's Distilling - Cannon Street Parking Lot (Between Cross & Mill Streets)
  • Live music, amazing food and drink, and fun for everyone. Join us in downtown Chestertown for Second Saturdays, sponsored by Bad Alfred's Distilling! This event is held rain or shine.

    Guests ...

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