The Chestertown Spy began for me with a phone call one wintry day in 2008. Dave Wheelan reached out while I was in Michigan, asking my thoughts about starting a publication in Chestertown. Having just come off publishing a print monthly on the Eastern Shore and Michigan, and wrestling with rising printing costs, I warned him it would be a hard road.
But Dave had a different vision: an online platform built from the ground up, publishing community news 24/7 with a focus on arts, education, and civic life. By the time I returned to Chestertown in 2009, the Spy was already underway along with a growing audience that valued its daily presence.
I joined part-time in 2015, became editor in 2020, and last year took on the role of publisher. Over the past year, Dave and I have worked on a redesign of all the Spy platforms—launching this Fall—to make them easier to read and more engaging for our communities.
Why does this matter? Because local news is disappearing. Since 2005, more than 3,300 newspapers have closed. At the same time, we face increasing pressure on First Amendment rights and the erosion of the nonprofit sector that sustains so much of community life here in Kent County. In this fragile moment, independent local journalism is not a luxury, it’s a necessity.
At the Spy, our job is simple: to tell the stories of people and organizations committed to the greater good. One day that might mean interviewing the school superintendent about the new Middle School project: the next, a health specialist about immunizations, or an op-ed on Maryland’s history of gerrymandering. And always, we highlight our region’s artists, musicians, and educators—the cultural life that makes our community thrive.
Our readers are thoughtful, civically active, and deeply invested in the Eastern Shore. But sustaining this work requires resources. While community sponsorships and advertising keep us afloat, our current revenue of $7,000/month does not allow us to hire the part-time reporters we need to cover government, schools, healthcare, and the many issues shaping our future.
We are very excited as we unveil our newly designed Spy platform. The old model sustained us for 15 years. In the meantime, technology changed and readership engagement changed—72%+ readers use their phones to read the Spy! So we have designed a more reader-friendly platform and are in the process of refining our category sections for easier scrolling. There’s even a feature on the right hand side of the to let you boost the text size, or translate the Spy into any language.
Additionally, and especially, The Chestertown Spy is elated to have Francoise Sullivan join us as Associate Editor, Site Designer and Systems Manager.
To do all this, we’ve set an ambitious fundraising goal of $70,000 — funds that will sustain our independent reporting, support local writers and photographers, and ensure that The Chestertown Spy continues to serve as Kent County’s trusted source for news, ideas, and community connection.
P.S. If you believe, as we do, that an informed community is a stronger one, please consider making a tax-deductible contribution today. Every dollar helps keep local journalism alive and accessible for everyone on the Shore.
I hope you’ll consider supporting the Spy as we take this next step. Your gift of any size directly strengthens local journalism and ensures Kent County continues to have a daily, independent voice.
Help Keep the Spy’s Light Burning by donating here
With gratitude,
Jim Dissette, Publisher/Editor
Francoise Sullivan, Associate Editor
The Chestertown Spy
2 Responses
The Spy is a treasure! One of the crucial conduits for local news, politics, and the arts.
Jim, you’e said it well, the demise of local news sources, the atrophying of independent journalism, and telling local as well as regional stories to the community. An informed community is hugely important, but it’s also how community members learn where they can engage, what’s important to them to act on to either help move forward positive change or prevent steamrolled decisions that will negatively impact the community, region, country. It’s how people can feel agency in their own lives and the lives of those around them. One reason tyrants and wannabe emperors try to strike down fact-based reporting is it distances human beings from their sense that their lives make a difference in the whole and that they can engage and rally their neighbors to prevent disasters. YES we support the Spy and will continue to as long as we can. Keep up the good work!