Ten Years of Spying in Chestertown

Ten years ago in a disheveled shed behind my Chestertown home, a small button was pressed, starting a new era for a hyper-local news source for a town I had fallen in love with when I first appeared on Washington College’s campus in the fall of 1974.

That spring of 2009 was filled with many unknowns for this publisher. Born in the midst of the great recession with very little evidence that this radically new educational format would be used or appreciated, this fledgling enterprise had no identified sponsors. It was less than certain that the Chestertown Spy, named after the town’s first newspaper that started in 1793, would survive much longer than its namesake’s 18 month lifespan.

Fast forward to 2019, and the Spy continues to publish every day and now serves an annual readership of over 400,000. And more importantly, our readers are coming to this website for all the right reasons.

They come to the Spy as a trusted media source and to better understand our community affairs, local arts, and the Mid-Shore’s regional culture.

It perhaps takes a decade before a founder is able to reflect on the value of an innovation. With the primary goal of simply existing day to day, there is no real opportunity to assess whether an experiment is actually working.

But now in the spring of 2019, after the publication of some 5,000 original articles and 3,000 video profiles, there is some rationale for looking back on the last ten years. And as a result, there is the reassuring conclusion that the original intent of having this hybrid newspaper be perceived as useful has worked.

It is also in these moments that when I reflect on the Spy’s accomplishments, the overused but accurate cliché, “it takes a village,” emerges as the fundamental reason for the Chestertown Spy’s success.

From the earliest advertisers — Chesapeake Architects, Chesapeake Bank and Trust, and Cross Street Realty — to the local journalists, filmmakers, and internet specialists who make the publication possible today, the Spy from Day One was able to rely on both the monetary and intellectual generosity of this community.

But it has also been the cumulative impact of a multitude of small gestures of support that made this success story happen. From the gentle emails telling us of typos, alerting us to people and programs needing attention, or just as importantly, criticizing the Spy on its editorial judgment, bias, or digression from our mission, are examples of caring that sustain and comfort its editors and writers.

All of this warm-hearted support and tough love has made the Spy so much better than I had ever imagined it would be. And as a result, I am extremely humbled.

Starting last year, we launched an annual campaign to cover the invisible but very real costs of running the Chestertown Spy. Editors do receive modest stipends, and the Spy also incurs a handful of monthly expenses for technical support, art design, and a variety of web service fees and subscription services that add up.

While our sponsors and their ads help pay for many of these costs, a small portion of the operating budget can only be covered through the donations of our readers.

I apologize in advance for the Spy’s use of pop-up ads to encourage these donations starting today. These are a genuinely annoying but necessary tool in gaining the attention of our readers. We promise they will end at the end soon.

But in the meantime, please consider making a tax-deductible donation this month so we can continue to spy on Chestertown for many years to come.

With gratitude,

Dave Wheelan
Founder and Executive Editor