Signature Events

Experience the vibrant spirit of Chestertown through its annual Signature Events, where the town comes alive with culture, community, and celebration. From the beloved traditions of the Chestertown Tea Party Festival to the lively Chestertown Jazz Festival, each event offers a unique glimpse into the town’s rich history and lively character. Explore our calendar of Signature Events and discover the best of Chestertown’s year-round festivities.

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 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


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


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 4th

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. 

Downrigging Weekend

First Weekend in November For 2024

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.

Dickens of a Christmas

First Weekend in December

Set in the Historic District, the festival celebrates the season with live music, carriage rides, Victorian food and drink, costumed characters, entertainment and more. Dickens of a Christmas is hosted by Main Street Chestertown and all proceeds further Main Street’s work to make downtown Chestertown a vibrant community.