The First Spy in 1793The Chestertown Spy began with a simple idea: to revive the spirit and civic purpose of the first newspaper printed in Chestertown in 1793, and to do so in a modern, digital form.
The original Spy promised to report not only on local “occurrences,” but also on political, commercial, agricultural, and cultural life, along with poetry, ideas, and news from beyond the region. It is believed that an informed community depends on curiosity, range, and careful observation.
When the Chestertown Spy was relaunched in 2009, it set out to honor that same mission for the 21st century. From the start, it focused on public affairs, local arts, and regional culture, using digital tools such as video, audio, and photography, and linking local stories to a wider context.
Chestertown was the natural place to begin. In many ways, it remains much as it was two centuries ago: a small, engaged community shaped by agriculture, the river, and a strong liberal arts tradition. Then as now, scholars, artists, writers, and performers move in and out of town, enriching civic life. The Chestertown Spy was created to observe, record, and share that life.
As the publication grew, it became clear that the need it served in Chestertown existed well beyond town limits. Local newspapers across the Mid-Shore were shrinking or disappearing, leaving gaps in coverage of town government, schools, arts organizations, and community life. At the same time, the demand for reliable, locally grounded reporting remained strong.
For that reason, the Spy model expanded into Talbot County, Cambridge, and Centreville. Each publication serves its own community, but all grow directly out of the original Chestertown Spy. The traditions, standards, and approach established in Chestertown continue across all Spy sites.
The Chestertown Spy did not simply inspire these publications; it began the tradition. The others exist because the model has proven its value and because neighboring communities have requested the same kind of journalism.
We do not see the Spy Newspapers as papers of record. Instead, they aim to provide clear, responsible, and meaningful coverage of public affairs, the arts, and local culture, offering small communities the depth of reporting more often associated with larger markets.
It is not entirely clear why the original publisher chose the name Spy in 1793. The simplest meaning, however, still fits: the discovery of something through observation. That remains the guiding idea behind the Chestertown Spy and the publications that followed.
April 15, 2009
Dave Wheelan
Founder