Every May, the good people of Chestertown gather to celebrate a local legend that may, or may not, have actually happened. And honestly? That just makes it more fun.
The Chestertown Tea Party Festival commemorates a spirited day in 1774 when a band of rebellious residents, inspired by the famous Boston Tea Party, supposedly marched down High Street to the Chester River, climbed aboard the British brigantine Geddes, and tossed its tea cargo into the water.
Did it really happen? Historians still enjoy debating that point over cups of tea (or perhaps something stronger). The records are a little murky, the details a little fuzzy, and the evidence… well… delightfully inconclusive. But one thing is absolutely certain: Chestertown knows how to throw one spectacular party every Memorial Day weekend.
The festivities kick off Saturday with the parade at 10 a.m., and trust us, you do not want to miss it. Think marching bands, colonial costumes, community groups, waving flags, and enough small-town charm to make your heart burst just a little.
At 2 p.m., crowds gather along the waterfront for the famous tea tossing reenactment, where tea (or empty boxes posing as tea) once again meet the Chester River in dramatic fashion. Then on Sunday at 2:30 p.m., the hilariously unpredictable Raft Race takes center stage, featuring homemade vessels that float with varying degrees of success.
In between all the tea-tossing excitement, four bustling downtown blocks are packed with live music, food vendors, artisan booths, games, performances, and activities for all ages.
To help you make the most of your Tea Party weekend, we asked our team to share their favorite festival traditions:
Emily — “I love the parade. It includes a little bit of everything and perfectly captures the magic of small-town life.”
Elizabeth — “The raft race on Sunday is my favorite. It’s quirky, unexpected, and wonderfully silly.” Pro tip: the best viewing spot is from Wilmer Park.
Melissa — “The activities on the Courthouse Lawn are always so much fun. There are games and crafts for kids, the Punch and Judy puppet show, and it also happens to be my favorite place to sit and enjoy clam strips.”
Karyn — “I like to grab a lemonade and an ice cream and walk around looking at all the different things and the people in their Colonial attire.”
Abigail — “The parade is my favorite and just all the people Tea Party brings to a small town.” Pro Tip: Use the shuttles to get around Tea Party. Park your car at one of the three free lots and walk around the festival grounds.
John — “The re-enactment and watching people really get into the spirit of the day.” Pro Tip: Get down to the river front early to get a prime viewing spot and take part in a sea chanty sea-along.
Jenn — “Seeing our tiny town bursting at the seams with visitors and locals. It’s a fun change for the sleepy pace, and such a great opportunity for folks to plan their next day trip.”
And new this year, right outside Chester River Wine & Cheese — the sister store to Welcome Home — you’ll find Vanilla Creations by Jennifer Stinnett serving up vanilla bean lemonade and gourmet cookie mixes made with top-shelf organic ingredients. Because nothing pairs better with revolutionary spirit than a really good cookie.
A complete schedule of Tea Party weekend events can be found here.
