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.

  • 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

  • Movie Night At The Garfield Presents: Santa Claus Conquers the Martians

    The Martians kidnap Santa Claus because there is nobody on Mars to give their children presents.

  • Second Saturdays in Chestertown

    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 of all ages are welcome to attend. Free public parking is available on High Street, Cross Street, and Cannon Street. There are two public… Continue Reading Second Saturdays in Chestertown

  • Nutcracker in a Nutshell at the Garfield

    Tchaikovsky’s holiday classic, slightly revised and only 30 minutes in length. Presented by students of Ballet with Becky. Free, Donations suggested.  

  • Rivers to Canal

    Join the wineries of the Rivers To Canal Wine Trail; Broken Spoke, Chateau Bu De and Crow Vineyard; for an afternoon of wine tasting coupled with holiday shopping. Your ticket includes tastings at each winery, a souvenir "Rivers to Canal" glass, a holiday shopping experience with local artisans and shuttle bus service between the three… Continue Reading Rivers to Canal

  • Festival of Trees-Dickens of a Christmas Weekend

    This is a community event that allows the community for all ages to visit a display of trees decorated by businesses, organizations as well as families. This is our way of saying thank you to the community for helping Soroptimist with the betterment of women and girls. Our Christmas Tree display is free and open… Continue Reading Festival of Trees-Dickens of a Christmas Weekend

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

    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 Chester Cemetery, a section of the rail trail and Wilmer Park. Part of the annual Dickens of a Christmas weekend, the run ends with a cup… Continue Reading "Run Like the Dickens" 5K Run/Walk

  • WACappella

    WACappella is Washington College’s Student A cappella group. They will be performing on December 7 at 7:30 pm in Hotchkiss Recital Hall. This is a free concert.

  • WACappella

    WACappella is Washington College’s Student A cappella group. They will be performing on December 7 at 2:00 pm in Hotchkiss Recital Hall. This is a free concert.

  • Dickens of a Christmas

    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-themed food and drink, children's games, expert talks, and vendors selling hand-crafted gifts.

  • Dickens Holiday House Tour

    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, the tour is planned to be easily walkable.

  • Festival of Trees-Dickens of a Christmas Weekend

    This is a community event that allows the community for all ages to visit a display of trees decorated by businesses, organizations as well as families. This is our way of saying thank you to the community for helping Soroptimist with the betterment of women and girls. Our Christmas Tree display is free and open… Continue Reading Festival of Trees-Dickens of a Christmas Weekend

  • 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

  • WACappella

    WACappella is Washington College’s Student A cappella group. They will be performing on December 6 at 7:30 pm in Hotchkiss Recital Hall. This is a free concert.

  • 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)

  • 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

  • Dickens of a Christmas

    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, and special entertainment to set the mood for a joyous holiday season.

  • Festival of Trees-Dickens of a Christmas Weekend

    This is a community event that allows the community for all ages to visit a display of trees decorated by businesses, organizations as well as families. This is our way of saying thank you to the community for helping Soroptimist with the betterment of women and girls. Our Christmas Tree display is free and open… Continue Reading Festival of Trees-Dickens of a Christmas Weekend

  • 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 2019 – January 2020 Opening Reception – December First Friday – December 6, 5-7:30 pm Please note: We will be closed on Sunday, December 8, to provide a dressing area for the Dickens of a Christmas ladies. Don’t miss this wonderful holiday weekend in Chestertown! New work by Gallery Artists and special guests. Featuring… Continue Reading MassoniArt presents Holiday Exhibition

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!