Every Memorial Day weekend, the Chestertown Tea Party Festival fills the streets of our little town with colonial chaos! It isn’t just a nod to history—it’s a full-blown reenactment of rebellion, complete with colonial garb, parades, music, and reenactments of the local legend of tea tossing into the Chester River.
Steep (pun intended) yourself in history on your next Memorial Day getaway. History buffs and casual visitors alike are welcome to one of Chestertown’s most iconic events.
Chestertown Tea Party History
The Tea Party Festival commemorates a little-known part of Maryland’s early history. While most are familiar with the events surrounding the Boston Tea Party, few know that there were other “tea parties” in other towns along the East Coast, including Yorktown, Charleston, Annapolis, and of course, Chestertown!
Legend has it that in 1774, Chestertown’s Sons of Liberty, outraged by British tea taxes and inspired by their revolutionary brethren in Boston, adopted the Chestertown Resolves—laws banning the purchase, sale, or consumption of English tea. When a British brigantine arrived with tea onboard, locals boarded it in broad daylight, openly dumping its cargo of British tea into the river—no disguises, no secrecy (unlike Boston’s protest, where the dumpers wore masks).
Since the U.S. Bicentennial in 1976, it has become an annual tradition that unites the community in a spirited celebration of local patriotism. Today, the event is more celebratory and educational than rebellious. The schooner SULTANA, a reproduction of a 1768 colonial British merchant vessel, serves for the reenactment as the British merchant ship Geddes, the original ship that was the target of the town’s ire.
About the Tea Party Festival
We highly recommend coming in your colonial garb and joining the fun! The festival begins Friday evening with a lively Block Party in Wilmer Park, with live music, food trucks, and vendors. While the reenactment and parades are the highlights, there are plenty of other exciting events to enjoy over the weekend:
- Heritage Village: Located on the Courthouse lawn, this area features colonial-era crafts demonstrations, including rope making, woodworking, and flax dressing.
- Artisan Vendors and Food Stalls: Over a hundred vendors line the streets, offering handcrafted goods and delectable local fare such as crab cakes (a Maryland staple and delicacy), barbecue, and the ever-popular funnel cakes.
- Children’s Activities: Families can enjoy puppet shows, colonial games, craft activities, storytelling, and face painting.
- The Chestertown Tea Party Beerfest: Don’t forget to sample local craft brews while enjoying live music and scenic river views on Sunday at this event.
Festivities kick off with the Chestertown Tea Party Distance Run, featuring 5K and 10-mile courses that wind through the scenic streets of this historic town. Afterward, history buffs and fans of Revolutionary War Reenactments will love seeing the costumes of the Colonial Parade, which takes place on High Street at 10 a.m. and showcases colonial militia, marching bands, and children in period costumes.
The big event, the Chestertown Tea Party reenactment, starts at 2 p.m. Crowds gather along the Chester River to witness costumed reenactors march down High Street, storm the schooner SULTANA, and dramatically cast crates of tea overboard.
The festivities continue into Sunday at Wilmer Park, where the Annual Raft Race at 2:30 p.m. invites participants to navigate the Chester River aboard creatively constructed rafts made from non-nautical materials.
Parade Information
The Chestertown Memorial Day Parade is a fantastic example of our town’s laid-back charm and friendly community. You won’t find anything like it in Baltimore or D.C.! Plan to attend the parade this year, which always features veterans, firefighters, antique vehicles, and the ever-fabulous Kent County Community Marching Band. In the past, the Budweiser Clydesdales have even made an appearance! The parade begins on Saturday at 10 a.m. by Dixon Valve and Coupling Co.
Have a Tea Party at Brampton 1860!
What better way to commemorate and share in the fun of the Chestertown Tea Party Festival than with your own Maryland tea party? Join us for Tea Time & Social Hour at our historic Maryland Inn. Brampton 1860 offers guests tea, appetizers, and refreshments in the dining room every afternoon.
Our inn rests on 35 beautiful acres of meadows, landscaped gardens, and forest. Our bright and beautiful rooms and cottages offer respite from the hustle and bustle. Here, you can sit back, relax, and “porch surf” with us (trust us…it’s a thing)! A short distance from Chestertown, it is the perfect place to stay for your Memorial Day weekend getaway.
You won’t want to miss the Chestertown, MD, Tea Party Festival and Memorial Day Parade this year. Book a stay with us now so you can start looking forward to the advent of summer!
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