Tidewater Trader was created in 1981 by Carla F. Johnson, who began the business at home with a pair of scissors, rubber cement, typewriter, and the kitchen table, churning out the first edition as an eight-page tabloid. Carla singlehandedly reached out to advertisers, designed and laid out the paper, and distributed the end product herself. In 1984, Tidewater Trader purchased its first computer and hired its first employee. In 1988, Tidewater Trader moved into the old train station, continuing to flourish and develop in its service to the community.
The train station building was originally a Historic Railway Station built in 1902–03 for the Pennsylvania Railroad. Today it remains the only station in the state of Maryland. For more information on the history of the building visit the Maryland Historical Trust page for the Chestertown Railroad Station.
In August of 2016, Tidewater Trader moved to a new location at 813 High Street in Chestertown, providing much needed room for its continued growth. With its dedication to personal customer service and community service, Tidewater Trader continues to be the "local people's paper" that is a go-to source for those living in and visiting the Kent, Queen Anne's, and Cecil County areas in Maryland, and in Lower New Castle County in Delaware.