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.
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 April-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 & Saturday After Thanksgiving
Welcome Santa to Chestertown at Fountain Park! Santa arrives by firetruck during the Kent County Holiday Parade and takes pictures with children at his holiday house. The parade starts at Dixon Drive and ends at Fountain Park.
Shop Small Saturday at Chestertown’s downtown shops and merchants.
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.
National Music Festival
June
The National Music Festival transforms Kent County into a hub of music. The nationally recognized event will feature music to suit virtually every taste — from symphonies and chamber music to hints of jazz. More than 30 concerts and over 200 open rehearsals are scheduled throughout the festival in venues across the Eastern Shore.
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.