Chestertown MD Events Happening on May 22-25

Thinking of a visit to lovely Chestertown, MD this weekend? You’ve certainly picked a great weekend to join us, as there are two big draws! First, we have the Chestertown Tea Party Festival: a local tradition steeped in history and mixed with a street-fair vibe. Second, this weekend kicks off the Schooner SULTANA Public Sails season!

Chestertown Tea Party Festival

Flag-1776-DT42482523You may have heard of that famous “Tea Party” up in Boston in December of 1773, but did you know that Chestertown residents of the time did the exact same thing here on the Chester River just a few months later?

It was all about the Tea… and England’s attempt to strongarm the American Colonies and make money through a series of taxes on items that were commonly used in both business and daily life. When the 13 Colonies reacted negatively, England repealed all of these taxes… save for the tax on tea.

Let’s think about this for a moment: the 13 American Colonies were British… the British LOVE their tea – so much so that afternoon Tea Time is still practiced throughout England today. It is almost impossible to fathom why the England would put a tax on such an important item here in America, but not in England… until you realize that England was just trying to demostrate its power over the New World. This action enraged the Colonies so much that revolt was inevitable: first in Boston, then in Chestertown, Annapolis and Charleston (not in that particular order).

The point was made in Boston by the Sons of Liberty who dressed up like Mohawk Indians to board three ships in the harbor and dump a total of 10,000 pounds of tea into the water.

The Chestertown branch of the Sons of Liberty didn’t bother with the disguises: on May 23, 1774 a gathering of men boarded the brigantine Geddes in broad daylight (in their own clothing) and threw the tea overboard. At least, that’s how the story goes…

It is in the spirit of American Pride mixed with a tiny seed of rebellion that the local Tea Party Festival began here in 1968. The event has grown from a parade and historic re-enactment to the multi-day celebration of today.

Each Memorial Day Weekend, the Tea Party Festival attracts both locals and visitors to our town for the biggest event of the year! Starting Friday, May 22, High Street is closed off from Mill Street to the Chestertown River for this annual street-fair-type celebration.

Oh, but it’s so much more than just a street fair… The event begins with a Street Party on Friday May 22. Saturrday could be called the “main event”, as the day – and the street – is filled with food and art vendors, musicians and dancers performing throughout the venue, the Colonial Parade, historic walking tours, kids’ activities, foot-races, Tea Party re-enactment, and some unique and amusing happenings throughout the day (Toss the Tory, anyone?).

The fun continues on Sunday with more of the same, except foot-races are replaced with a Raft Race at Wilmer Park! A full schedule can be found at the Chestertown Tea Party website.

There is so much happening at the Festival that you may not have time to experience it all. But if the full schedule isn’t enough, this weekend marks the start of:

Schooner SULTANA Public Sails

Schooner-DT15808683Saturday, May 23 starts the sailing season for the Schooner SULTANA. This beautiful cargo schoner/yacht hybrid is used as a classroom by the Sultana Education Foundation, whose mission is to offer education about the Chesapeake Bay, its history, and its culture to both children and adults.

Today’s SULTANA is a replica of the original 1768 merchant vessel which was actually a part of the British Royal Navy. Its job was to sail along the Colonial coastline enforcing the dreaded Tea Tax. So of course the start of today’s SULTANA┬ásailing season coincides with the Chestertown Tea Party Festival!

The sailing season happens on select weekends throughout the summer and early fall, including general, educational and music sails. Trips are approximately two hours long and run $30 for adults and $15 for children between the ages of 5 and 12 (special pricing applies for music sails, oyster sails and the Downrigging Weekend).

You’ve selected a great weekend to come to Chestertown, and Great Oak Manor hopes to host your Memorial Day Weekend visit!


Want to learn more about the Schooner SULTANA? Sultana Projects, Inc., offers an informative brochure in .pdf format which includes history of the original ship and detailed information about its replica including deck blueprints and plenty of photos.