The Wayne Gilchrest Trail, which opened on Earth Day in 2012, runs along the southern edge of the historic Maryland Eastern Shore community of Chestertown. The trail connects Washington College to the Chestertown business district and is named for the former congressman whose 2003 federal earmark made development of the trail possible.
Start your journey at popular Wilmer Park on the Chester River. The trail begins just across S. Cross Street/State Route 289 from the park, where an original train station has been converted to office use. Because the trail occupies an abandoned rail corridor that last saw freight service in the early 1990s, trail users are treated to a flat surface and gentle curves.
From the old train station, the rail-trail parallels Cannon Street adjacent to some of the town’s charming residences. A turn to the northeast shortly thereafter takes bikers and walkers to High Street. In the future, Chestertown plans to construct an extension to the trail running adjacent to High Street; this spur will connect to additional residences to the north of the town.
Across High Street, the trail passes an industrial property before entering the campus of Washington College. The trail runs along the entire length of the campus of the 10th oldest college in the United States before ending at Morgnec Road/SR 291.