Main Street Chestertown

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...

Downtown Master Plan Release

Downtown Master Plan Release

Press Release March 25, 2024 Main Street Chestertown and local partners are embarking on a Downtown Master Plan with Design Collective, Inc., a Baltimore-based consulting firm, to envision the future of Chestertown’s Historic District. Working in concert with the...

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 colonial-era...

Facade Improvement Grant Program

Facade Improvement Grant Program

The Spring 2024 application period will open March 1, 2024. The due date for applications will be March 31, 2024. For more information or an application, please contact the Main Street office. ABOUT THE PROGRAM  Main Street Historic Chestertown (MSHC), with...