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 village in Lunenburg County, 46 miles west of Halifax, in the province of Nova Scotia, Canada. According to Chester’s town minutes, Elmer E. Horsey, then Mayor of Chestertown, and his Council, requested them by letter, to be their Companion City.

According to the Kent News, “The affiliation is envisioned as an opportunity to see ‘a growing awareness and appreciation of each other’s culture and people.’” As part of their relationship, both towns exchanged a variety of local gifts around the Christmas holiday from 1987 through 1999. For many years a fresh-cut Chester tree could be found decorated in the Chestertown Town Hall. And in 1989, Mayor Horsey presented Warden Percy H. Shatford with a Key to the City of Chestertown. Both dignitaries visited between towns during their terms and encouraged others to do the same.

-Marianne L. Sade, Historical Society of Kent County Volunteer, 2018