What’s Happening: Downtown!

Chestertown Marina by Sam Shoge

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


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.

  • Osprey 5k & Fall Festival

    Held on the beautiful grounds of Kent School in Chestertown, MD, the Osprey 5k is a family friendly event welcoming athletes at all levels of skill and experience. The race will consist of a 3.2-mile run. The course will cover mixed surfaces, including pavement, gravel paths and some grassy areas. Racers under the ages 10 must be accompanied by a running partner at least 16 years of age. We hope you'll stick around after the race to enjoy the Fall Festival, an event of the Kent School Parents, Teachers, and Friends Association. The event will feature fun activities for the whole family! […]

  • Fall [Re]Build Day

    ReBuilding Together Kent County volunteers will visit Kent County neighbors and offer a FREE Home Safety Checkup. Call, Click or Text! Let us know you want to participate. Please provide your name and address—that’s it! We’ll do the rest! Call us or text your information to 410-708-9936 or Register online at RebuildingTogetherKCMD.org […]

  • Run the Vineyard – Crow 5k

    Run for Wine at at the Amazing Crow Vineyard!Race and Post Race Features Include: Timed Run with results Flat Cross Country style course through the 365 acre farm and 12 acre vineyard Post Run Wine (1 complimentary glass of wine included for those 21 and older) Live music by Greg Jones til Noon! On Site food vendors throughout the morning Lawn games for all! Free downloadable Photos Tech Shirt and Souvenir wine glass for all participants ***Shirt choices guaranteed if signed up before Sept. 11, 2019 Awards for Fastest Runners (Top 3 Overall, and Top 3 per age Group) Walkers Welcome to Sign U […]

  • Movie Night At The Garfield Presents: The Little Princess

    A little girl is left by her father in an exclusive seminary for girls, due to her father having to go to South Africa to fight in the Second Boer War. […]

  • Foraging & Feasting: A Presentation by Dina Falconi

    Dina Falconi, clinical herbalist with a strong focus on food activism and nutritional healing, will kick off the Center for Environment & Society’s 20th Anniversary Events Series on Sept. 17. The free and public presentation will begin at 5:30 p.m. in the Litrenta Lecture Hall at Washington College’s Toll S. Center, followed by a book sale and signing. Falconi’s Foraging & Feasting Presentation will explore the culinary treasures hidden in wild foods. Learn to identify, harvest, and prepare these ancient foods so you can easily incorporate them into your daily meals. […]

  • 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 parking lots downtown. One between Cross & Mill Streets on Cannon Street, and two between Cross Street and Queen Street along Cannon Street. […]

  • First Annual Chestertown Car Show

    The monthly Cars on High auto-enthusiast gatherings partners with Main Street Chestertown to create a downtown Car Show. Come admire a variety of vehicles from custom hotrods to classic and antique beauties. Category prizes, food and beverages, children's activities, and car-related contests will contribute to a fun afternoon that welcomes all. Event is free to the public. A modest registration fee is required for each car entered in the show. For information and to register, email: ChestertownCarShow@gmail.com. […]

  • Kent Goes Purple Community Jamboree


  • Jazz Festival

    Our 2019 LineupAlicia Olataju, headliner Gregor Huebner Greg Thompkins Quintet WC Jazz Combo […]

  • 5th Annual CrowFest

    A Celebration of the Eastern Shore’s Bounty! Farm & Vineyard Festival. Live music, food & wine seminars, crafts, tours, hayrides, grape stomping, great food and much more! […]

  • Music in the Park – Summer Concert Series

    8/2/19 Update: Well, global warming is apparently not our friend this summer. The director of Swing City has decided to postpone this Saturday’s planned concert due to the heat along with the possibility of thunderstorms. The temperature is predicted to be in the 80s at 7 pm with of course a higher “feels like” temperature. This is especially difficult weather for musicians playing trumpets and other wind instruments. The band is too large to fit into our usual back-up locations. However, there’s good news! We have rescheduled both of our postponed bands for one big Music in the Park Saturday on Sept 7. We’ll send out details later, but right now it looks like the Chesapeake Brass Band will go on at 2:00 pm and Swing City will follow them around 4:00 pm. So mark your calendars for a big day of music in downtown Chestertown at Fountain Park (and keep your fingers crossed for good weather!) […]

  • Charlie Joiner Memorial Decoy Show

    First Annual Charllie Joiner Memorial Decoy show honoring the late Charlie Joiner, native of Betterton & Chestertown Md. and a world renowned Decoy carver from Kent County Maryland.. We are expecting close to 100 Vendors for this one day event that will include new decoys, old decoys, antique fishing lures, shell boxes, oyster cans, fishing and hunting licenses and much more. Proceeds from this event will benefit the Charlie Joiner/Charlie Bryan Investment Account at the Havre de Grace Decoy Museum. Admission is just $5.00. Come out and support this legendary art to our area from the past and in the future. A great day for the family. […]

  • Emmanuel Church Concert Series

    Tim Robinson, organist, returns for a program of organ and Horn music with Cary Ebli, English Hornist with the Toronto Symphony Orchestra. […]

  • Connections: Work in a Series – Opening Reception

    The idea of working in series or in distinct purposeful directions is not about repetition but rather about being able to explore, investigate, examine or address ideas, themes, issues, compositions, concepts or topics in progressively deeper and more meaningful ways, and from a greater variety of perspectives than is possible by making just one or two.Come in to explore the connections the artists have made with their series of work. Exhibit on display from September 6 – 29, 2019 Gallery Hours: Tuesday-Friday, 11:00 am – 5:30 pm Saturday, 10:00 am – 5:30 pm Sunday, 11:00 am – 3:00 pm […]

  • September 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 our wonderful Kent County bed and breakfasts. Saturday morning check out the Chestertown Farmer's Market, and our other quaint Kent County towns of Rock Hall, Galena, and Betterton. #kentcountymd #chestertownmd #visitkentcounty […]

  • MassoniArt presents TREES

    TREES tree-ness September 6 – October 13 Opening Reception – September First Friday, September 6, 5-7:30 pm Closing Reception – October First Friday, October 4, 5-7:30 pm Vicco von Voss ,Grace Mitchell, Simma Liebman, Patrick Henry, Joe Dickey,Paula Shalan, Eve Stockton, Katherine Cox, Blake Conroy, Heidi Fowler, Linda Richards, Stu Cawley, Mark Gardner, Robert Ortiz, Takashi Ichihara,Vanna Ramirez, Lindsay Mullen, Lisa Lebofsky, Zemma Mastin White,Marcy Dunn Ramsey, Emily Kalwaitis, Nicole Fall, Karen Hubacher,Deborah T. Colter, Anne Nielsen and special guests. 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 by chance. Private appointments may be scheduled at any time by contacting Carla Massoni – 410-708-4512. Of course, you are always welcome by chance – if you see the lights on – just knock! […]

  • 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 […]

  • Dancescape Auditions

    Washington College’s Department of Theatre and Dance invites you to open auditions for Dancescape.Performances are Friday, November 22 at 7:30 AM and Saturday, November 23 and 2:00 PM. All levels are welcome, beginning to advanced. For questions, please contact A.T. Moffett, Visiting Assistant Professor of Dance. amoffett2@washcoll.edu. […]

  • 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 there’s always a cash bar. Donations are always appreciated. […]

  • Ease Back Pain – Part 3 of The Benefits of Therapeutic Touch Series

    Kiley Shipp, LMT, SET, presents the last of a 3-part series exploring how massage and body work techniques can help you address common body aches and pains.    Please register. Wednesday, August 28 – Ease Back Pain Gain a better understanding of the inconnectedness of your anatomy, including how working the muscles in your legs and stomach can help alleviate back discomfort. […]

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


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!