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Celebrate Chestertown’s Colonial Heritage

Chestertown Colonial Tea Party Festival

May 24-26, 2019

Join the Revolution! Chestertown Tea Party Festival May 24 – 26

The town of Chestertown invites everyone to join them in celebrating its colonial past with the 43rd annual Tea Party Festival, Memorial Day Weekend, May 24- 26.  This festival commemorates the 1774 event, where, in revolt against British tax on tea, local lore has it the disgruntled citizens marched down to the Chester River and tossed tea overboard from the brigantine Geddes.

The festival kicks off Friday at 6 pm with a free Street Party at the foot of High Street, on the water’s edge, complete with music by Del Fox, craft beer and a  variety of food trucks. Saturday starts with the Chestertown Tea Party Classic Run (5k or 10 miles).  The popular Colonial Parade begins at 10pm, featuring marching bands – including the award winning Largo High Marching Machine, and the US Army Old Guard Fife & Drums.

Step into the 19th Century at the Colonial Village, and view a military unit encampment, complete with a blacksmith, seamstress, Cabinet of Curiosities, and colonial dancing.  Children’s activities include a Punch & Judy puppet theatre, facepainting, story telling and a  jug band. There is even a chocolate maker!
Guests can enjoy the more than 100 craft vendors lining the street, take a historic walking tour, and partake of local food.

New this year – Levram the Great, a colonial conjurer, will perform two shows at the Garfield Center for the Arts, followed by a Crankie! What’s a Crankie? A moving panorama is an old story- telling form, an illustrated scroll set onto spools in a viewing box. The artwork is hand cranked and accompanied by a narrative or song. This Crankie will be accompanied by Crankie artist Katherine Fahey and Marc Dykeman ( of the High & Wides band).

Another do not miss show at the Garfield, Sumner Hall’s musical presentation of the story of Ona Judge, slave of Martha Washington, featuring singer Karen Somerville and a cast of 19 musicians, singers and dancers.

Main Stage entertainment features popular bluegrass/old time/hillbilly string music band, the High & Wides, the Rock Candy Cloggers and the seafarin’ group, the Jolly Tars.

The much – anticipated Tea Party Re-enactment begins at 2pm, with colonists marching down the street to the water and rowing out to throw the Tea overboard.

The Party continues Sunday, in Wilmer Park, along the scenic Chester, with crafts, food, children’s activities, live music featuring Joe Holt and Brad Chaires, local wine & beer tasting, and Sunday’s highlight, the annual Raft Race at 2pm. Who will win the coveted Tea Party Cup?

In addition, the Edna Lockwood, the last historic sailing bugeye in the world, will be visiting Chestertown over Memorial Day weekend as part of a National Park Service-funded heritage tour around the Chesapeake Bay.  Owned and operated by the Chesapeake Bay Maritime Museum, Edna Lockwood recently underwent a two-year restoration of her nine-log hull. During her stay, CBMM staff members will offer free deck tours, giving guests a chance to explore the bugeye while she’s docked. Open for tours 10 am – 4 pm.

For more information please visit and join in the revolution!


If you are thinking of staying over for the weekend go to



2019 Edna Ross Award Recipient – Ralph Dowling/People’s Bank!

The Edna Ross Award is given annually to a local business person for outstanding service to the community. The award was created by Chestertown Tea Party Festival organizers in 2011 to honor Ross and all she had done for Chestertown.



2019 Grand Marshal – Andy McCown!

The Chestertown Tea Party Committee is proud to announce that Captain Andrew McCown of Betterton is this year’s Honorary Grand Marshal.  “Cap’n Andy” will be temporarily trading his customary perch atop a Tea Party Re-enactment barrel to kick off the weekend events.


McCown, a Chestertown native, has been involved with the Chestertown Tea Party Festival since its inception.  He recalls painting roadside signs about the first festival for festival founders Sonny Usilton and Louis Anthony.


He first participated in the re-enactment as a student at Washington College in 1973, and he has participated in every re-enactment since with exception of only four that he was unable to attend.


Since 1978 Andrew has been the organizer of the script and all of the actors and actresses. There are often locals that he calls on to participate, but the majority of the re-enactors are fellow outdoor educators from Echo Hill Outdoor School where Andrew is an Associate Director.


In addition to Andrew’s extensive involvement in the re-enactment, he served faithfully on the Board of Directors of the Tea Party for many years.


McCown has been an educator with Echo Hill Outdoor School since 1977.  He currently also serves as Associate Director, Director of Summer Programs, and Director of the Historic Fleet at EHOS.


An accomplished spoken word artist, Captain Andy performs with the group Chesapeake Scenes, paying tribute through songs and stories to the people who live and work on the waters of the magnificent Chesapeake Bay.


McCown has been extensively involved on the board of ShoreRivers and the Chester River Association for many years, championing the river he loves.

The Parade Grand Marshal rides in the parade and greets festival goers!