Kent County Arts and Entertainment Events- December 2024


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  • RiverArts Annual Holiday Show & Sale

  • Sunday,
  • This event runs November 9 to December 22
  • Location: Chestertown RiverArts - 343 High Street
  • Contact: Chestertown RiverArts
  • Phone: 410-778-6300
  • Email: info@chestertownriverarts.org
  • URL:  https://www.chestertownriverarts.com/holiday-show
  • Celebrate your holidays and the joy of gift giving at RiverArts Holiday Show & Sale — certainly one of the most popular places to shop on the Eastern Shore!

  • First Friday Joe Holt & Jimmy Lawlor "Tribute to Lois Prima"

  • Friday,   |  8:00pm
  • Location: The Mainstay - 5753 N. Main St
  • Contact: The Mainstay
  • Phone: 4106399133
  • Email: info@mainstayrockhall.org
  • URL:  https://mainstayrockhall.org/shows/
  • Joe Holt’s Final First Friday welcomes the swing-blues sounds of drummer and vocalist, Jimmy Lawlor in a tribute to the songs of Louis Prima and Louis Jordan Jimmy Lawlor, a member of the Midiri Brothers Group, will sing and swing in a show that will pay tribute to the exciting tunes given to us by the great Louis Prima (“That Old Black Magic”, “Jump, Jive, and Wail) and Louis Jordan (Is You Is or Is You Ain’t My Baby”) Joining them will be Dave Schiff on sax, Max Murray on bass, and special guest vocalist Sharon Sable.

  • Wreaths Friends and Fun!

  • Sunday,   |  1:00pm - 3:00pm
  • Location: Brampton 1860 - 25227 Chestertown Rd, Chestertown MD 21620
  • Contact: Brampton 1860
  • Phone: 410-778-1860
  • Email: innkeeper@bramptoninn.com
  • URL:  https://www.eventbrite.com/e/wreaths-friends-and-fun-tickets-1081473499349?aff=oddtdtcreator
  • Wreath Making Workshop

    Kick off the holiday season by creating a beautiful seasonal wreath with Brampton 1860's resident wreath designer Donna!

    Join us for a fun afternoon creating a wreath with friends, sipping wine and enjoying afternoon snacks. Wreath form, materials, decorations, instruction, and tools will be provided – just be ready to have a good time and share in the holiday spirit! You will have a beautiful wreath to take home!

  • Open Mic Night at The Mainstay

  • Wednesday,   |  7:00pm
  • Location: The Mainstay - 5753 N. Main St
  • Contact: The Mainstay
  • Phone: 4106399133
  • Email: info@mainstayrockhall.org
  • Join us for Open Mic Night. No ticket fee.

  • A Feast of Carols! Chester River Chorale holiday concert

  • Friday,   |  7:30 pm
  • Location: Presbyterian Church of Chestertown - 905 Gateway Dr
  • Contact: Chester River Chorale
  • Email: info@chesterriverchorale.org
  • URL:  https://www.chesterriverchorale.org/performances/a-chester-river-holiday-2024/
  • Experience the heartwarming tradition of Christmas caroling with the Chester River Chorale's "A Feast of Carols." This program features beloved arrangements by David Willcocks, John Rutter, Alfred Burt, Ola Gjeilo, Rollo Dilworth, and more, all celebrating the rich history of wassailing on a grand scale with our 100-voice community choir and professional chamber orchestra. Join us for an unforgettable night of music, community, and holiday cheer!

    Please bring a donation for the Food Pantry. New this season, tickets may be reserved online.

  • Chestertown A&E Holiday Art Walk

  • Saturday,   |  10:00 am to 3:00 pm
  • Location: Chestertown A&E District - Downtown Chestertown
  • Contact: Chestertown Arts & Entertainment District
  • Phone: 410-778-3700
  • Email: hester@kentculture.org
  • URL:  https://townofchestertown.com/residents-3/art-and-culture/
  • 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 happening throughout town. For information email hester@kentculture.org or call the Kent Cultural Alliance at 410-778-3700

  • A Feast of Carols! Chester River Chorale holiday concert

  • Saturday,   |  4 pm
  • Location: Presbyterian Church of Chestertown - 905 Gateway Dr
  • Contact: Chester River Chorale
  • Email: info@chesterriverchorale.org
  • URL:  https://www.chesterriverchorale.org/performances/a-chester-river-holiday-2024/
  • Experience the heartwarming tradition of Christmas caroling with the Chester River Chorale's "A Feast of Carols." This program features beloved arrangements by David Willcocks, John Rutter, Alfred Burt, Ola Gjeilo, Rollo Dilworth, and more, all celebrating the rich history of wassailing on a grand scale with our 100-voice community choir and professional chamber orchestra. Join us for an unforgettable night of music, community, and holiday cheer!

    Please bring a donation for the Food Pantry. New this season, tickets may be reserved online.