Events - Main Street Chestertown

Chestertown Events

Enjoy Chestertown's Year-Round Festivities

Farmers' & Artisans' Market

300 High Street
June 25, 2022 8:00 am - 12:00 pm

Carnival on High

200 High Street
July 1, 2022 5:00 pm - 8:00 pm

Chestertown Car Show

200 High Street
October 1, 2022 12:00 pm - 4:00 pm

Dickens of a Christmas

200 High Street
December 2, 2022 5:00 pm - 5:00 pm

Music in the Park

Fountain Park
July 9, 2022 7:00 pm - 7:00 pm

Music in the Park

Fountain Park
July 23, 2022 7:00 pm - 7:00 pm

Music in the Park

Fountain Park
August 20, 2022 7:00 pm - 7:00 pm

Baltimore Symphony Orchestra

413 South Cross Street
August 6, 2022 7:00 pm - 9:00 pm

Saturday in the Park

413 South Cross Street
July 23, 2022 11:00 am - 8:00 pm

Check Out Our Signature Events All Year Long!