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Chestertown Tea Party Festival
The Chestertown Tea Party festival is a time honored tradition for visitors and residents alike. This weekend long festival has entertainment for all ages. Kick off the Tea Party weekend […]
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Annual Event
National Music Festival
The National Music Festival transforms Kent County into a hub of music. The nationally recognized event will feature music to suit virtually every taste — from symphonies and chamber music […]
“Heroes of the Chesapeake” Juneteenth Celebration
Friday, June 14th, 2024, and Saturday, June 15th, 2024, the Bayside H.O.Y.A.S., will host their annual “Heroes of the Chesapeake” Juneteenth celebration at Fountain Park in Chestertown, Md. This two-day […]
Brampton 1860 Open House
Brampton 1860 25227 Chestertown Rd, Chestertown, MD, United StatesJoin us for an Open House at Brampton 1860! Explore the historic charm of Brampton 1860 a boutique hotel and venue located at 25227 Chestertown Rd. This in-person event offers […]
Free
Crazy Days
Hosted by the Downtown Chestertown Association, Crazy Days is Chestertown’s annual sidewalk sale with businesses offering crazy deals and restaurants offering crazy specials.
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Downrigging Weekend
The Sultana Education Foundation's Downrigging Weekend highlights Tall Ships and Bluegrass, along with nautical history and Chesapeake Bay ecology.
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Hometown Holiday
Kick off the Holiday Season with one of Downtown Chestertowns most iconic events, the arrival of Santa and Mrs. Clause on a fire truck! Enjoy the festive holiday music, candy, […]
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Dickens of a Christmas
National Music Festival
The National Music Festival transforms Kent County into a hub of music. Now in its 13th season, the nationally recognized event will feature music to suit virtually every taste — […]