What is the Wayne Thomas Gilchrist Trail? Commonly called the Wayne T. Gilchrist Trail that was named after a local politician that served in the U.S. state of Maryland and in Washington, the trail is on an old rail line that winds its way through the town of Chestertown located on the Chester River on the Eastern Shore Region of the U.S. state of Maryland. It is also known as the Chestertown Rail Trail.
The history of the railroad in the town of Chestertown, Maryland is unknown as the town was much more of a port town on the Chester River than a railroad town. It is known the railroad line was once a spur line that connected to a main railroad line in Delaware that ran south from Wilmington, Delaware down the center of the Delmarva Peninsula to the town of Pocomoke City, Maryland and then to the town of Cape Charles in the U.S. state of Virginia at the southern end of the peninsula where the Chesapeake Bay enters into the Atlantic Ocean. A railroad ferry transported the train across the mouth of the Chesapeake Bay to Norfolk. (Much of the track in Virginia is no longer active while the active section in Maryland and Delaware is owned by the Norfolk Southern Railway.) Although the Pennsylvania Railroad originally built the line. Smaller short line railroads owned the different spur routes.
Back in the glory days of railroading when the railroads ran both passenger and freight services, the passenger trains served small towns on spur lines like Chestertown. When Amtrak service began, passenger service to small towns on spur lines ceased, and passenger service ceased on the main railroad line on the Delmarva Peninsula, and the opening of the Chesapeake Bay Bridge connecting the east and west coasts of the Chesapeake Bay aided the decline.
What is known about the railroad line? At the southern end of the rail trail is an old passenger train station and an old freight house where two old passenger cars and a red caboose are on display. Between the passenger and freight stations appear to be an area that appears to be the site of an old railroad yard. The trail runs north from here and ends on the north side of the town.
Today, the Wayne T. Gilchrist Trail is the only reminder of Chestertown being a railroad town. It is a reminder of how the railroad was a big part of small town America.
John Cowgill: Stories of the Railroad 