Upcoming Events in Chestertown

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

Chestertown Farmers Market

20 December 2025

Chestertown, MD

Chestertown Farmers Market, 118 N Cross St

Washington vs. York (PA)

15 November 2025

Chestertown, MD

Casey Swim Center, 300 Washington Avenue, Bldg# CSATH3

Washington vs. Swarthmore

08 November 2025

Chestertown, MD

Casey Swim Center, 300 Washington Avenue, Bldg# CSATH3

Washington vs. Salisbury

30 January 2026

Chestertown, MD

Casey Swim Center, 300 Washington Avenue, Bldg# CSATH3

Live Playwrights’ Society Monthly Meetings

02 March 2026

Chestertown, MD

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