Chesapeake Wine Trail Event at the Chestertown Tea Party
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ANNUAL SNEAKER CREEPER Foot Race Just For Kids (2 thru 11) Rain or Shine
Sneaker Creeper
Enjoy delicious food and drinks provided by volunteers from local non-profit organizations. The Chestertown Tea Party Festival is one of the largest fundraisers for non-profits in the area.
Food Concessions
Thousands of festival-goers line High Street to cheer the passing of colonial militia, marching bands, costume-garbed children and a variety of other participants in the festival’s parade. Boasting a colonial-theme, the parade prohibits automobiles ...
Colonial Parade
Enjoy the many characters and performers you will encounter throughout the day! Check the schedule for the list of musicians and performers who will be on stage and wandering the festival!
Schedule of Events
Over 100 colonial artisans and craft vendors display and sell their work. Many artisans also provide demonstrations throughout the day.
Artisans and Craft Vendors
The guilty shall be tossed!
Tory Toss
Every Spring during the Chestertown Tea Party Festival an elite group of highly trained athletes gather at the edge of the Chester River and prepare for a competition that will test their ability to plumb the depths of imagination and maintain delusional ...
Raft Race
In response to British Parliament’s closing of the port of Boston, the citizens of Chestertown met in May of 1774 and set forth “Resolves” forbidding importing, selling, or consuming tea in Chestertown. According to local legend, residents then ...
Chestertown Tea Party Festival Reenactment
Sample local wine and beer on Saturday and Sunday.
Regional Wine and Craft Beer Tastings
10 Mile Run & 5k Run/Walk. Course is USATF - Maryland Certified MD08011JS.
Classic Distance Run
