Main Street Chestertown is Hiring!

Main Street is currently seeking a new full-time Executive Director to begin immediately. For more information and to apply, click the button below

Companion Cities: Chestertown

Companion Cities: Chestertown

In case you were wondering why there is a Canadian flag flying in front of the Chestertown Maryland Town Hall…..here’s how it came to be. Since 1987 Chestertown, Maryland has been the Companion City of the municipality of the district of Chester, a waterfront...
A Beacon of Faith: The History of Emmanuel Church

A Beacon of Faith: The History of Emmanuel Church

Emmanuel Episcopal Church stands as a timeless testament to faith, community, and history. Established in 1692, just years after the founding of the town itself, Emmanuel Church has been a cornerstone of the Chestertown community for over three centuries, witnessing...
Get Married in Chestertown

Get Married in Chestertown

A Guide to Getting Married in Maryland’s Historic Gem Nestled along the banks of the Chester River, Chestertown, Maryland, exudes historic charm and timeless beauty, making it the perfect setting for a romantic wedding. From its quaint streets lined with...