Give your getaway an exciting twist with some of the great Chestertown, MD festivals and events. Experience fantastic seasonal events in Autumn and Christmas time, immerse yourself in the area with historic happenings like the Chestertown Tea Party Festival, or simply relax with Music Down on the River on weekends in the Summer. Whatever event you decide to attend, let our Eastern Shore bed and breakfast be your tour-guide to everything unique and interesting the area has to offer.


Garfield Center for the Arts at the Prince Theater – Their mission is to invigorate the cultural life of the community by nurturing, celebrating and supporting arts and artists through performance and education.

The Mainstay – Located in Rock Hall, The Mainstay features a diverse offering of concerts by local, regional, national, and international musicians all at a reasonable ticket price.

Church Hill Theatre – A community theatre located in Church Hill that has been around for over 35 seasons.

Music in the Park – Held every other Saturday in Chestertown’s Fountain Park (June through mid-August)

Music Down by the River – Summertime weekends

Local Annual Events

Chestertown Tea Party Festival – Held every Memorial Day Weekend, Chestertown celebrates its colonial past.

National Music Festival – During the first two weeks of each June, this festival combines world-class mentor musicians and gifted pre-professional apprentice musicians. Come and watch these musicians present over 30 concerts and more than 200 free open rehearsals for music lovers.

Pirates and Wenches Fantasy Weekend – A town-wide theme party in Rock Hall that you won’t soon forget. Typically held mid-August.

Chestertown Harry Potter Festival – Calling all Potterheads to the fifth annual Harry Potter Festival. The first weekend of October.

Rock Hall’s Fall Fest – Held in October as a celebration of family, community, and oysters! Enjoy live music, craft booths, food, and more.

Sultana Downrigging – Tall ships headed back to home port. Visitors to the festival can expect to see a waterfront packed with ships, schooners, and wooden boats. As well as performances by world-class musicians, and lectures by authors and filmmakers.

Dickens of a Christmas – A Victorian holiday extravaganza typically held the first weekend in December.

For specific dates, we encourage you to view the Kent County Calendar of Events.