What’s Happening: Downtown!

Kent County’s Live Stream Events: What’s Happening

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Kent County is always bursting with festivals, events, and other activities and we love a parade. Want to plan your calendar? Check out our always-updating feed for what might bring you to town again and again.

  • December First Friday

    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 held the first Friday of every month and everyone is welcome and encouraged to join us. Make it a night with a stay at one of… Continue Reading December First Friday

  • Washington College Music Department Vocal Recital

    The Department of Music will present a Vocal Recital featuring students from the studios of Carolene Winter and Bennett Umhau. This concert is free and open to the public.

  • MassoniArt presents Holiday Exhibition

    December 6 – January 12 Save the date! Gallery hours* are subject to change based on our exhibition schedule. When we are installing a new exhibit the gallery will be dark. Otherwise our hours are Thursday thru Friday 11-4pm, Saturday 10-5 pm, Sunday 11-2 pm. We are closed Monday thru Wednesday except by appointment or… Continue Reading MassoniArt presents Holiday Exhibition

  • Washington College Symphonic Band, Jazz Ensemble and Saxophone Chamber Music

    The Department of Music presents the Washington College Symphonic Band (Keith Wharton, Director), Jazz Ensemble (Jon Steele, Director) and Saxophone Ensemble (John Thomas, Director). This event is FREE and open to the public.

  • The Garfield Center Presents: Live Playwrights’ Society

    The Live Playwrights’ Society for Play Writers, Readers, Observers & Critics aims to foster a community of playwrights, actors and critics. This group meets the first Monday of every month at 7:30pm and is open to all ages. For more information visit http://liveplaywrightssociety.org

  • Percussion Chamber Music

    The Percussion Ensemble, under the direction of Eric Plewinski, will present a showcase that explores the many different colors, timbres, and diversity of sounds that these instruments are able to produce. This event is free and open to the public.

  • Small Business Saturday in Chestertown

    Kickstart the holiday shopping season by shopping small and shopping local with your Chestertown independent merchants. As you shop, grab a ticket to win fantastic prizes donated by your local neighbor merchants, gallery owners, artists, and restaurants. There will be music, food, wine & spirits, and fabulous shopping all over town.

  • Annual Holiday Parade

    Parade starts at 10am Crowds line High Street to enjoy an old fashioned holiday parade with floats, marching bands, and favorite characters. The Jolly Old Elf himself brings up the rear.

  • Saturday Mornings at KidSPOT!

    KidSPOT is a hands-on creative learning center for children aged 2-12. We are open every Saturday free of charge to kids accompanied by their parents, or other responsible adult. The Center is a destination for area children where they can look forward to interacting with a variety of stimulating activities that expand their horizons. Located right… Continue Reading Saturday Mornings at KidSPOT!

  • Chestertown Farmers Market

    On Saturday mornings from 8 am to noon beginning about the third Saturday in March and ending about the last Saturday in December, located in beautiful Fountain Park in the heart of downtown Chestertown, on Maryland’s Eastern shore you’ll find wonderful fresh home grown produce, herbs, breads, soaps, plants and cut flowers as well as… Continue Reading Chestertown Farmers Market

  • Open Mic Night at the Garfield

    Open Mic Night with Ford Schumann at the Garfield Center for the Arts at the Prince Theatre! Play music on your own or with a band, read some poetry, do a stand-up routine. The options are limitless. E-mail Ford Schumann at fordo1@aol.com to sign up, or for more information! There’s no price to come, and… Continue Reading Open Mic Night at the Garfield

  • Washington College String Orchestra and Chorus Concert

    The Department of Music presents the Washington College Chorus, under the direction of Ernie Green & String Orchestra, under the direction of Kimberly McCollum. This event is FREE and open to the public.

  • Saturday Mornings at KidSPOT!

    KidSPOT is a hands-on creative learning center for children aged 2-12. We are open every Saturday free of charge to kids accompanied by their parents, or other responsible adult. The Center is a destination for area children where they can look forward to interacting with a variety of stimulating activities that expand their horizons. Located right… Continue Reading Saturday Mornings at KidSPOT!

  • Emmanuel Church Christmas Bazaar

    A variety of holiday items for sale, including Elegant Elephants, Botanical Delights, Gourmet goodies, Holiday ornaments, Jewelry, and more. All proceeds go to local charities.Lunch served from 11:30 a.m. to 1:30 p.m.

  • Chestertown Farmers Market

    On Saturday mornings from 8 am to noon beginning about the third Saturday in March and ending about the last Saturday in December, located in beautiful Fountain Park in the heart of downtown Chestertown, on Maryland’s Eastern shore you’ll find wonderful fresh home grown produce, herbs, breads, soaps, plants and cut flowers as well as… Continue Reading Chestertown Farmers Market

  • Annie: The Musical (Nov 22 – Dec 8)

    November 22 – December 8 Fridays & Saturdays at 7pm, Sundays at 2pm 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 determined to find the parents who abandoned her years ago on the doorstep… Continue Reading Annie: The Musical (Nov 22 – Dec 8)

  • 2019 Holiday Show/Gift Sale Opening Reception

    The Annual RiverArts Holiday Show features gifts for every pocketbook. These unique gifts created by our members include everything from children’s clothing to jewelry, fashion accessories, home decor, stocking stuffers, holiday cards and ornaments, paintings and more.

  • Washington College Students Honors Recital

    The Department of Music presents the Student Honors Recital. Student soloist and chamber ensembles are selected for this concert via competitive audition. This event is FREE and open to the public.

  • The Conservatory Classic Jazz Band Plays Louis Armstrong

    The Conservatory Classic Jazz Band is the third edition to this year's concert series. This group encompasses a diverse collection of artists who together have performed all over the United States and in other countries. Performing music from the legendary jazz musician Louis Armstrong this night at Sumner Hall will truly be one to remember.

  • MassoniArt presents Marc Castelli Annual Exhibit

    King’s Tide – Annual Exhibition October 25 – November 27, 2019 also featuring Chesapeake Boat Models by Ken Castelli Opening of the Exhibition & Reception Friday, October 25, 5-7:30pm Collector’s Preview – October 21-24 – by appointment November First Friday Celebration November 1, 5 -7:30 pm Marc Castelli – Gallery Talk Saturday, November 2 –… Continue Reading MassoniArt presents Marc Castelli Annual Exhibit

Chestertown’s Farmers Market Is Back In Business

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Chestertown’s Farmers Market is both a destination market that draws folks from all over and also a very community-spirited occasion. Totally focused on “local,” you can buy seasonal goods ranging from fruits, vegetables and meats to fresh flowers, soaps, and artfully created artisan works. See you next Saturday? Click here for additional info!

Calling All Cars: Come on Down to Cars on High

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Every third Thursday, from April through October, 6 to 8 pm, weather permitting. The schedule for 2019 includes April 18, May 16, June 20, July 18, August 15, September 19, and October 17.

Auto enthusiasts meet to share their classic, antique, and exotic wheels with the public.  Click here for additional info!

Calendar: Downrigging Weekend November 1 – 3

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The 19th Annual Downrigging Weekend will take place November 1 – 3. Organized by Chestertown’s own Sultana Education Foundation, this tall ship and wood boat festival is a cherished experience. Events include tall ship tours and sailing expeditions, enrichment lectures, musical concerts, 5K races and fireworks.

Click here for additional info!

Calendar: Chestertown Tea Party Festival May 24 – 26

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Can you believe this year marks the 44th annual Chestertown Tea Party Festival? The weekend, chock full of events surrounds the main event: A re-enactment of tossing tea overboard to support the Boston Tea Party. As well, don’t miss the parade, juried crafts stands, food trucks, music and more!

Click here for additional info!