Arts and Entertainment







Kent County Maryland Calendar of Events- September 2021


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September 3

Stephen Phillip Harvey Big Band
  • Stephen Phillip Harvey Big Band

  • Friday,   |  8:00 PM
  • Location: The Mainstay - 5753 N. Main St.
  • Passionate about both jazz and pop culture, composer Stephen Philip Harvey never shies away from blending both into his writing. In his current large ensemble project, Harvey uses contemporary big ban...

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September 9

25th Annual Chestertown Jazz Festival
  • 25th Annual Chestertown Jazz Festival

  • Thursday,   |  7 to 9:30 pm
  • Location: Mainstay
  • Join us for 3 days of fabulous jazz featuring national and regional artists.

    The 25th Annual Festival begins Thursday, September 9 at the celebrated venue The Mainstay in Rock Hall with Chuck Red...

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Charlie Byrd Tribute with Chuck Redd
  • Charlie Byrd Tribute with Chuck Redd

  • Thursday,   |  8:00 PM
  • Location: The Mainstay - 5753 N. Main St.
  • The Chuck Redd Quartet performs its annual tribute to Charlie Byrd. Special guests to be announced...don't miss it!

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September 10

25th Annual Chestertown Jazz Festival
  • 25th Annual Chestertown Jazz Festival

  • Friday,   |  6 to 9:30 pm
  • Location: Wilmer Park - Wilmer Park
  • Join Us for a Gala Cocktail Party & Concert under the Festival Tent in WIlmer Park, in celebrating the 25th Anniversary of The Chestertown Jazz Festival.

    Enjoy cocktails & heavy hors d...

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September 11

  • MassoniArt presents MARCY DUNN RAMSEY Geometries

  • Saturday,
  • This event runs September 11 to October 11
  • Location: MassoniArt - 203 High Street - MassoniArt - 203 High Street
  • Marcy's annual exhibit

    Also featuring work by Michael Kahn and Katherine Cox

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25th Annual Chestertown Jazz Festival
  • 25th Annual Chestertown Jazz Festival

  • Saturday,   |  noon to 6 pm
  • Location: Wilmer Park - Wilmer Park
  • An Afternoon in Wilmer Park of Fabulous Jazz featuring

    Christian McBride’s New Jawn
    Chestertown Jazz Festival Revue
    Sue Matthews, Uptown Jazz Vocal Quartet, Lena Seikaly, Dick Durham, Stef ...

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  • Sultana Public Paddle - Tuckahoe

  • Saturday,   |  10am - 12:30pm
  • Location: 200 S. Cross Street
  • Join Sultana Education Foundation’s staff naturalists for one (or more!) of our unique kayak paddles on Maryland’s Upper Eastern Shore. Kayaks for these trips are provided so all you need ...

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September 16

  • Cars on High

  • Thursday,   |  6:00 to 8:00 p.m.
  • Location: Downtown Chestertown - 300 block of High Street, by Fountain Park
  • This series of gatherings takes place in downtown Chestertown every third Thursday of the month, April through October, from 6:00 to 8:00 p.m., weather permitting. The Town closes the 300 block of Hig...

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September 18

  • Sultana Education Foundation's Annual Gala

  • Saturday,   |  6-10pm
  • Location: Clovelly Farm
  • September 18, 2021 6-10pm...Cross your fingers and join the Sultana Education Foundation at the hottest event in town. Great food, open bar and entertainment featuring live music, dancing and maybe ev...

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Ellen Cherry
  • Ellen Cherry

  • Saturday,   |  8:00 PM
  • Location: The Mainstay - 5753 N. Main St.
  • Emmy-nominated ellen cherry (lowercase letters intentional!) is an award winning song and story alchemist, musician and performer, based in Baltimore, MD. Mixing equal parts of pathos and humor throug...

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September 21

  • Sultana Public Paddle - Full Moon Paddle

  • Tuesday,   |  6:00 - 8:30pm
  • Location: 200 S. Cross Street
  • Join Sultana Education Foundation’s staff naturalists for one (or more!) of our unique kayak paddles on Maryland’s Upper Eastern Shore. Kayaks for these trips are provided so all you need ...

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September 25

  • Sultana Public Paddle - Ghost Fleet

  • Saturday,   |  10am - 12:30pm
  • Location: 200 S. Cross Street
  • Join Sultana Education Foundation’s staff naturalists for one (or more!) of our unique kayak paddles on Maryland’s Upper Eastern Shore. Kayaks for these trips are provided so all you need ...

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Danny Paisley and the Southern Grass
  • Danny Paisley and the Southern Grass

  • Saturday,   |  8:00 pm
  • Location: The Mainstay - 5753 N. Main St.
  • Deeply rooted in tradition but looking to the future with enthusiasm and anticipation. Powerful, unadorned and intense traditional bluegrass is on the menu tonight!...

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