Celebrate Chestertown’s Colonial Heritage

It’s not your typical street fair! Now in its 39th consecutive year, the Tea Party Festival in Chestertown, MD offers an engaging glimpse into its colonial past in addition to entertainment, children’s activities, crafts, wine and beer tastings, and more. Follow the re-enactment of Colonists and Tories as they march to the Chester River and board Chestertown’s 18th century tall ship, Sultana, to dispatch its cargo of tea overboard. Afterwards, you can take a public sail on the Sultana itself. Walking tours of the historic district, demonstrations of colonial crafts, revolutionary theater by local playwrights and the popular “Tory Toss” into the river all make for a fun and educational weekend.

The festivities start on Friday evening with a Street Party in front of the Garfield Center for the Arts. Enjoy BBQ, music and children’s activities.

Throughout the weekend, the Festival offers a broad range of music and performances. From accapella gospel groups to bluegrass, from strolling musicians, playing colonial music on authentic instruments, to local music groups, there is something for everyone. Several groups perform 18th century dances and the audience is more than welcome to join. The weekend would not be complete without theatrical performances at the Garfield Center for the Arts at the Prince Theatre. Enjoy two “Revolutionary Theatre” performances written by local playwrights.

The Festival provides many activities for those who are traveling with children. We start the day with a festive colonial parade. This year we are delighted that the U.S. Army Old Guard Fife and Drum Corps will be joining us. Afterwards, enjoy story times and Punch and Judy Shows on the lawn of Chestertown’s historic court house. This is also the site where the colonial re-enactors and regiments have set up camp. If you would like to see more of our historic downtown, a treasure hunt will take you and your family past many of our most valued buildings.

In addition, the Festival offers docent-led walking tours of the historic district. You can admire Chestertown from the river by taking a public sail on the 18th century tall ship, the Sultana (for reservations please visit festival would not be complete without a large craft fair and plenty of local food.

The festival concludes on Sunday afternoon with a wine and beer tasting event, the popular Raft Race in which teams compete to keep their home-made raft afloat for as long as possible and of course, more entertainment, crafts and food.

For more information about the Chestertown Tea Party Festival including a schedule of events, please go to website: For information about staying in Kent County for the weekend go to