Chestertown Tea Party Festival

May 19th, 2022

The Chestertown Tea Party Festival

Are you looking for a way to celebrate history, experience live entertainment, and explore Maryland’s beautiful Chester River? You’ll love attending the Chestertown Tea Party Festival, one of the most entertaining and educational things to do in Maryland! Here is an overview of its historical importance and events.

Where is Chestertown?

Chestertown, Maryland, is a relatively small waterfront community. The town sits on the banks of the Chester River, which feeds into the Chesapeake Bay. Although the town’s population is just over 5,000, this harbor area is full of things to do during all seasons of the year! You’ll love exploring Chestertown’s local shopping, trying fresh food at the restaurants and farmer’s market, and visiting the waterfront.

What is the Chestertown Tea Party Festival?

Chestertown’s unique and entertaining Tea Party Festival is a celebration of the town’s history. The festival offers entertainment, food, activities for both children and adults, and interesting education about the history of the town and the festival.

The three-day festival is typically held annually, although it had a brief two-year hiatus. In 2022, the Chestertown Tea Party Festival will be returning on Memorial Day Weekend, May 27-29. The festival is family-friendly and perfect for any history lovers, festival fanatics, and vacationers. Many different restaurants, buildings, parks, and more will be hosting this year’s festival fun!

What Is the History Behind the Tea Party Festival?

The fascinating history behind the Chestertown Tea Party begins in 1773, when, before the United States’ liberation, the British Parliament placed a heavy tax on American residents. Outraged at the taxation without representation, Boston colonists dumped loads of tea into the harbor in protest. This event became known as the Boston Tea Party and was one of the first steps in the United States defying Great Britain.

By May of 1774, the Boston harbor was shut down by Great Britain. In response to this, residents of Chestertown held their own Tea Party. The citizens banned the consumption, sale, or import of tea as an act of rebellion called the Chestertown Resolves. As legend has it, in a final act of protest, the town’s citizens copied the Boston Tea Party and dumped tea from the docked boats into the harbor.

Now, the Chestertown Tea Party is celebrated to remind people of the importance of the rebellion that happened that day. The festival is meant to educate the citizens of Maryland (and the United States) on the importance of the rebellion against Great Britain.

What Events Can You Attend?

The Chestertown Tea Party is a three-day celebration with many things to do. You’ll never have a moment of boredom during this festival! Enjoy reenactments, live performances and music, a parade, and more.

Historical Reenactments and Education

One of the most interesting things to do in Maryland is learn about the rich history of the area. The Chestertown Tea Party is one of the most historic events in its part of Maryland. Each year, the festival hosts reenactments and educational activities to teach festival-goers about this exciting history.

Past festivals have hosted a Tea Party reenactment, where members of the community gather in the center of the town. Men in traditional colonial dress parade down the street to the harbor where the famous Tea Party occurred. The parade also features local marching bands, children dressed according to the era, and other floats.

Additionally, the Tea Party Festival always features educational lectures, performances, tours, and more. Join a walking tour of the community to learn about the different historical landmarks, visit with vendors selling their crafts, and watch exciting live performances!

Heritage Village

Are you interested in souvenirs, art displays, and delicious food and drink? Heritage Village is a neighborhood hosting vendors and artists during the festival. The vendors and talented artists sell and display a wide variety of things, including Maryland souvenirs, historically accurate items, plus amazing food and drink.

Family-Friendly Activities

The Tea Party Festival is always great family fun. This coming year, the festival will have many activities for children, performances for all ages, a raft race, pyro-musical fireworks, and more. Children can visit the many different art stands, tours, and vendors around the town to find engaging and educational activities.

The annual raft race is another family-friendly event. Anyone is able to sign up for the raft race, where all rafts have to be built out of nontraditional materials. Kids and adults will love watching the rafts try to race down the Chester River, and seeing who can stay afloat!

Besides these other family-friendly options, 2022 will be the first year to have pyro-musical fireworks. These are a type of fireworks that are programmed to synchronize with music. The display is sure to be jaw-dropping and exciting for all ages!

5k and 10k Run/Walk

Are you looking for a way to have fun while helping out charities? The historic festival’s annual 5k and 10k run/walk races are excellent events to take part in. The entrance fee for the run/walks is donated to local organizations, including the Radcliffe Creek School, which is an empowering special education program.

Both the 5k and 10k races will have prizes for those who finish the race first. However, not everyone who joins in on the 5k and 10k has to run! Participants are encouraged to join to walk the 5k and 10k and spend quality time with their friends and family.

Wine and Beer Festival

Are you a wine lover, a beer enthusiast, or just looking for a fun way to spend time with other adults? During the Tea Party Festival, Chestertown’s annual wine and beer festival is a great way to enjoy a cold beverage and relax. The festival has a wide selection of options for both beer and wine, and typically has food and non-alcoholic beverages available as well. There’s something for everyone!

Enjoy the Historic Chestertown Tea Party Festival with the Help of the Sutton Team at Coldwell Banker Chesapeake Real Estate!

Are you interested in experiencing all that Chestertown has to offer? Your dream home is waiting. The Sutton Team is ready to help you find your perfect home in Chestertown, Maryland. 

Billy Sutton and Lacey Sutton with The Sutton Team at Coldwell Banker Chesapeake Real Estate

The Sutton Team at Coldwell Banker Chesapeake Real Estate


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