Call for Artists! The Kent County Gateway Committee has opened the Gateway to Chestertown public art  competition, inviting artists and teams to propose a permanent landmark along Morgnec Road. The winning design  will celebrate the cultural, historical and natural identity of Kent County while creating a welcoming gateway to  historic Chestertown. Artist commission is $75,000!

The Garfield Center for the Arts has added a fun, Halloween-themed event to their 2025 schedule that will present an evening of music and feature a Costume Contest. “The Kitchen Sink of Horrors” will be presented on the GCA stage on Saturday, October 25th, starting at 8:00 PM. The concert is a fundraiser to support the GCA in advance of their capital improvements campaign. 

On Saturday, October 18, The Mainstay is excited to welcome back the extraordinary jazz pianist Dick Durham. Durham, one of The Mainstay’s most requested performers, is an annual visitor to the 28-year old non-profit music venue. Dick will be joined onstage by Max Murray on upright bass and Greg Burrows on drums.

Rock Hall Elementary School's annual Fall Farmers Market returns in October with free produce. This Community School event will be held from 3 to 5:30 p.m. Friday, Oct. 10 at Rock Hall Elementary School.

Kent School, an independent school serving children in Preschool 3 through Grade 8, will host its Fall Admission Open House on Tuesday, October 21 at 1:30 p.m for the Kindergarten through Grade Eight program. Families are invited to visit the School’s riverside campus located just outside of historic Chestertown to learn more about the benefits of a Kent School education.

University of Maryland Shore Medical Center (UM SMC) at Chestertown recently acquired a new state-of-the-art MRI machine at its diagnostics center located at 100 Brown Street. The new MRI replaces an older machine and represents substantial advancements in patient imaging technology. 

 WCTR Radio, the Eastern Shore’s locally owned and  independently operated radio station, is proud to announce the expansion of its  broadcast reach with the addition of a new frequency at 100.1 FM. This exciting  development will extend WCTR’s classic hits, community news, weather, sports, and  local programming to listeners across Queen Anne’s County, northern Talbot County,  and Caroline County.

About 20 3-year-olds had their first day in the classroom this month thanks to Kent County Public Schools' expansion of its prekindergarten program. The school system has long offered universal all-day pre-K for 4-year-olds. This fall, a Pre-K Expansion Grant from the state opened the door for 3-year-olds to join the program as well.

The Annual Chestertown RiverArts Studio Tour will take place this year on October 18-19, October 25-26 and November 1-2.

With more than $2 million in gifts and pledges in hand and  $300,000 remaining to be raised to meet the $2.3 million Together We Soar fundraising campaign goal, the Kent School Board of Trustees has authorized construction to begin on the eagerly-anticipated Middle School expansion project.