Chestertown Cash is our community’s own gift card program—designed to support the small businesses that make our town unique. Accepted at a wide variety of shops, restaurants, services, and boutiques, Chestertown Cash makes the perfect gift for friends, family, employees, and visitors.

Choptank Community Health System is proud to join communities across the country in celebrating National Rural Health Day on Thursday, November 20, 2025.

Kent County High School, in partnership with the Maryland Business Roundtable for Education (MBRT), is inviting local professionals and community members to participate in a series of volunteer opportunities designed to help students explore career pathways and develop essential workplace skills.

“Cinderella” opens Friday, December 5th and runs weekends through December 21st. Because itis a family friendly musical, Friday and Saturday evening performances start at 7:00 PM instead ofthe usual 8:00 PM start. Sunday matinees retain the 2:00 PM start time.

A fierce cross-county rivalry played out on the hardwood of Queen Anne’s County High School on Saturday, October 25th, as the Sheriffs’ Departments from Queen Anne’s County and Kent County came together for a cause.

On Saturday, November 22, The Mainstay Community Players will present another of their popular singalong tribute concerts.  This group of approximately 20 local musicians have prepared A Night at the Opry, celebrating the superstars of classic country music, the legends who defined the golden age of Nashville and the famed Opry House that marked the pinnacle of their careers.

In honor of Veterans’ Day this month, For All Seasons is bringing the focus to the mental health of families and caregivers of veterans, active service, and reserve members who can experience a unique set of challenges, stressors, and traumas, from deployment and combat to reintegrating into civilian life after leaving the military.

Kent County High School's administrative secretary was honored this month with the Golden Anchor Award for being everyone's "go-to person" in the building. Skyler Cochran received her award from the Kent County Board of Education Monday night, Oct. 13.

On Friday, November 7 the Mainstay is pleased to present a showing of “Death On the Chesapeake: A Hard Rain”, a new documentary film that explores the increasing number of threats the Chesapeake Bay now presents to its neighbors (flesh eating bacteria, drowning fish) and the straightforward explanation of its human cause. 

The next Safe Sitter® course, hosted by University of Maryland Shore Regional Health (UM SRH), will take place from 9 a.m. to 4 p.m. Saturday, November 8, at UM Shore Medical Center at Chestertown, 100 Brown St. UM SRH is a member organization of the University of Maryland Medical System.