Signature Events

Experience Chestertown's Signature Events

Chestertown is known for some long standing popular events that draw visitors from around the world. Join us for our next event, we promise good entertainment, good refreshments, and great people.

We are in the process of adding more signature events. Check back soon!

Farmers/Artisan Market

Every Saturday from 8am - 12pm

The Chestertown Farmers’ & Artisans’ Market is held year-round every Saturday from 8:00am until noon, rain or shine. The Market is held on the street in the 200 and 300 blocks of High Street, and Memorial Row. 

Chestertown Car Show

October

The Chestertown Car Show showcases the ultimate examples of automotive prowess. Vehicles range from vintage Model T’s to modern street racers. Prizes are awarded in ten different classes and overall. This event culminates the “Cars on High” series that runs every third Thursday from March-October. 

Downrigging Weekend

Last Weekend in October

The Sultana Education Foundation’s Downrigging Weekend Festival is one of the largest annual tall ship gatherings in North America. The festival features three days of Tall Ship sails, tours, live music, lectures, exhibits, family activities, regional food and more. Proceeds benefit the Foundation’s environmental literacy programs, partner school program scholarships and the other nonprofit’s participating in the festival.

Hometown Holiday

Friday After Thanksgiving

Welcome Santa to Chestertown at Fountain Park! Santa arrives by firetruck and takes pictures with children at his holiday house.

Saturday After Thanksgiving

All of the holiday favorites march into town during the Kent County Holiday Parade. The parade starts at Dixon Drive and ends at Fountain Park.

Hometown Holiday is co-hosted by Main Street Chestertown and the Downtown Chestertown Association.

Chestertown Tea Party Festival

Memorial Day Weekend

The annual Chestertown Tea Party Festival marks the anniversary of one of the area’s most notable historic events, when the citizens of Chestertown tossed a ship’s cargo of tea overboard into the Chester River in 1774. 

Paint The Town

June

Put on by RiverArts, this plein air event has artists paint the local scene and make their paintings available for sale. There is a two-hour Quick Draw; these paintings are then shown in Fountain Park, are judged, and also for sale. 

Juneteenth Celebration

Third Weekend in June

The Black Union of Kent County and the Town of Chestertown host the annual Kent County Juneteenth Celebration offering a series of events to celebrate history, culture, and achievements.

Independence Day Fireworks

July 4

Celebrate America’s birthday in a traditional Colonial town and watch a magnificent fireworks display over the Chester River. The fireworks can be viewed from both shores and the water.

Crazy Days

Late July

Hosted by the Downtown Chestertown Association, Crazy Days is Chestertown’s annual sidewalk sale with businesses offering crazy deals and restaurants offering crazy specials. 

Want to Know What's Coming Up Next?
Head to Our Main Events Page