Upcoming Events in Chestertown

The Rocky Horror Show

16 October 2026

Chestertown, MD

Garfield Center for the Arts at the Prince Theatre, 210 High St

DON’T WORRY, BE HEALTHY

09 September 2026

Chestertown, MD

Univ of Maryland Shore Medical Ctr at Chestertown, 100 Brown St

BREATHE AGAIN: A Journey to a Smoke Free

01 October 2026

Chestertown, MD

Univ of Maryland Shore Medical Ctr at Chestertown, 100 Brown St

Short Attention Span Theatre

19 June 2026

Chestertown, MD

Garfield Center for the Arts at the Prince Theatre, 210 High St

DON’T WORRY, BE HEALTHY

08 July 2026

Chestertown, MD

Univ of Maryland Shore Medical Ctr at Chestertown, 100 Brown St

Chestertown First Friday

03 July 2026

Chestertown, MD

MASSONIART - CROSS STREET GALLERY, 113 S Cross St

Toddler Time-Terrific Trees

14 November 2025

Chestertown, MD

Sultana Education Foundation, 200 S Cross St

BREATHE AGAIN: A Journey to a Smoke Free

05 March 2026

Chestertown, MD

Univ of Maryland Shore Medical Ctr at Chestertown, 100 Brown St

DON’T WORRY, BE HEALTHY

11 March 2026

Chestertown, MD

Univ of Maryland Shore Medical Ctr at Chestertown, 100 Brown St

Chestertown Farmers Market

27 December 2025

Chestertown, MD

Chestertown Farmers Market, 118 N Cross St