The Memorial Day weekend Chestertown Tea Party Reenactment pays homage to the 1774 event with pageantry, fun, and festivities.

chestertown tea party
It’s a grand time to be in Chestertown. History comes alive! Photo courtesy of Chestertown Tea Party Festival

When the Sons of Liberty, dressed like Indians, dumped bales of tea into Boston Harbor in 1774, that act of defiance and its rallying cry of “No taxation without representation” set the stage for what was to become the greatest “experiment in democratic self-government” ever conceived. 

This Memorial Day weekend in Chestertown, MD, a group of fun-loving brigands will board the schooner Sultana and replicate that act of defiance. But with much less severe consequences, unless you happen to be one of the reenactors playing the part of a Tory. In that case, be prepared to be tossed into the river along with the tea!

The Chestertown Tea Party reenactment harkens back to not only that original Boston Tea party and the subsequent closing of the port of Boston by the British, but also to an occurrence right here in Chestertown where reportedly a group of dissidents boarded the British ship Geddes and unceremoniously dumped tea into the Chester River on May 23, 1774.

Records are sparse about the specifics of the Chestertown Tea Party more than 250 years ago, and in fact the actual dumping of tea might never have happened. What is clear is that the booming port of Chestertown was very much caught up in the run-up to the American Revolution, and in addition to the passage of the Chestertown Resolves which stated that it was illegal to import, sell, or consume tea, such an overt act of rebellion certainly was not out of character for the patriots who populated many portions of the Eastern Shore.

chestertown tea party
Time to toss the tea! Photo courtesy of Chestertown Tea Party Festival

The modern-day Tea Party Reenactment is only part of an action-packed Memorial Day weekend festival with everything from a five- to 10K run; a Friday night street party; a parade on Saturday, May 25, featuring the reading of the Chestertown Resolves on the square followed by the march to the waterfront by the tea partiers; and then their row out to the anchored Sultana for the ceremonial tossing of the tea. There is no charge for admission to the festivities, although there are plenty of opportunities to spend money on food and beverages, particularly at the weekend’s craft beer and wine extravaganza. 

On Sunday, visitors can also enjoy walking tours of the historic district, demonstrations of colonial crafts, more than 100 craft vendors, children’s activities, local foods, a wine village beside the town dock, and a wide array of musical entertainers. The festival concludes Sunday afternoon in Wilmer Park with local wine and craft beer tastings, more entertainment, crafts, and food. The popular Raft Race is the main event at 2 p.m.; teams compete to keep their homemade raft afloat for as long as possible in hopes of winning the coveted Tea Cup.

Last year’s festivities included an appearance by the Budweiser Clydesdales. “We’ve reached out to them again this year,” says Chestertown Tea Party Festival president Sabine Harvey. “We hope they can come again, but we won’t know for sure until closer to the event. For sure, there will be plenty to do for history buffs, people who love good local food and spirits, and kids young and old. The festival has been a ‘happening on the river’ for 43 years. We expect to put on a good show rain or shine.”

Crowds swell the town of Chestertown to three to four times its population of 5500. “We roll out the red carpet for all our Tea Party visitors,” says Mayor Chris Cerino “even those with Loyalist persuasions.” 

Cerino cautions boaters to make plans early for slips at the newly refurbished Chestertown Marina. “We’re already booked, but you never know when somebody might cancel,” he says. Boaters are advised to check nearby marinas like Great Oak and the Chester River Yacht Club for transient accommodations. 

chestertown tea party
The raft race is a popular Sunday event. Photo courtesy of Chestertown Tea Party Festival

“Lots of people just anchor out to view the on-water activities,” Cerino says. “Just mind the ‘no anchoring’ zones we’ve established around the Sultana and the route the Colonists will take as they row out to toss the tea in the water.” To check on the Chestertown Marina availability, call City Hall at (410) 778-0500. 

Chestertown native Mark Mumford has been involved with the Chestertown Tea Party for over three decades. “The festival was originally started back in 1956 to commemorate the town’s 250th anniversary. It was revived in 1967 primarily by downtown merchants to bring shoppers back into the city. It’s a grand time to be in Chestertown. History comes alive. And we all work hard to make it fun.”

Mumford has recently retired as the Drum Major of the award-winning Kent County Community Band. He led the band down the streets of the colonial town for over 40 years. He was even named Grand Marshall of the Parade. “It’s pretty cool to march down past the old customs house at the foot of High Street… and conjecture what was going on at the waterfront those 250-plus years ago.”

Putting on the Tea Party is a community affair. A small organizing committee heads it all up, but a lot of the heavy lifting is done by a veritable army of Chestertown and Kent County volunteers. Reenactors are recruited from the nearby Echo Hill Outdoor School. Craft beer and wine vendors all hail from the surrounding area. 

For an up-to-date schedule of events, go to:

chestertown tea party
“The burning of the Peggy Stewart" by Francis Mayer, 1896

Annapolis's Tea Party is a roaring affair

In October 1774, the city of Annapolis was host to a tea party of another sort. Seems local merchant Anthony Stewart and his business partner Thomas Williams had imported 2000 pounds of tea and paid the tax so due. 

This Loyalist act raised the ire of locals, who ordered the ship burned where she lay at anchor. The ship, named the Peggy Stewart, was a new vessel. Her burning and the loss of the cargo of tea, no doubt caused much consternation to Stewart who, in addition to being burned in effigy, was forced to relocate to Canada shortly thereafter. 

He spent the rest of his years petitioning the British government for compensation for his losses. No compensation was ever paid. 

By Craig Ligibel