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Print Friendly MapThe Wayne Gilchrest Trail offers a scenic off-road route across historical Chestertown on the Eastern Shore, connecting Wilmer Park on the Chester River with Washington College on the north side of town. Also known as the Chestertown Rail Trail, the paved path is named for former US Representative Wayne Gilchrest, a noted environmentalist who in 2003 added trail funding to a federal spending bill.
The trail follows the route of the Kent County Railroad, which was opened in 1872. In those days, the trains hauled peaches, apples, and tomatoes to major markets and brought commodities to town. Bought and sold over the years, control of the line fell to the Pennsylvania Railroad in 1900. Passenger service to Chestertown ended in 1949, and freight ser-vice ended in 1996. The trail opened on Earth Day in 2012.
The rail-trail starts in the south near Wilmer Park, an old dockyard on the Chester River. A pavilion overlooks the river, which flows to Chesapeake Bay, and visitors can take a riverfront stroll or relax on benches. Founded in 1706, Chestertown became a wealthy town in Colonial Maryland due to the river trade.
At the trailhead on South Cross Street/MD 289, you’ll see a caboose and two vintage passenger cars parked outside an old farm-supply warehouse that now holds offices. Nearby, the trail passes the renovated train depot built by the Pennsylvania Railroad in 1903. Leave the trail here to find the town’s touristy business district two blocks up Cross Street.
Back on the trail, you’ll come to a junction 0.5 mile past the old depot. To the right, the trail follows the main rail line across High Street and then passes the western edge of the Washington College campus, a private liberal arts college whose founding in 1782 was funded in part by George Washington.
In late 2021, an extension was completed, continuing the trail another 0.3 mile to the Foxley Manor residential community; a pedestrian/bicycle signal will be added to the new route at the Morgnec Road/MD 291 crossing in spring 2022. Long-range plans call for extending the trail 3 miles north along the old railbed to the town of Worton.
Taking the left fork back at the junction, the trail follows a spur railbed behind businesses on High Street about 0.6 mile to parking at Gateway Park on High Street/MD 20. Across the street, the still-standing Radcliff Mill site, built in the 1890s, became an important railroad stop for local commerce.
Parking for the Wayne Gilchrest Trail can be found at the southern trailhead at Wilmer Park (413 S Cross St). The park is located just off S. Cross Street/SR 289 on the Chester River. Alternatively, park on the campus of Washington College near the trail's northern endpoint or by Gateway Park (872 High St).
Stretching for more than 2 miles across Chestertown on MD's Eastern Shore, the Wayne Gilchrest Trail is a scenic greenway that has the potential to connect to more communities.
Like many town-based trails, the paved, multi-use path allows residents to walk or bike between communities with minimal street crossings. It links Washington College with the north and south sides of town and the southern terminus along Cross Street is just a short distance from the waterfront at Wilmer Park as well as the historic downtown. Also notable is a spur of the trail that branches from the main path on the grounds of an office building and parallels High Street, connecting to the northwest side of town and ending at the former Radcliffe Mill, which has been restored and now houses a restaurant and microbrewery.
The trail also serves as an outdoor museum of sorts and features several sculptures and murals along the route, while the old train station, vintage passenger coaches and caboose at the southern end off Cross Street are a testimony to the rail line that used to run here.
Last, but not least, the lush vegetation that lines most of the trail's route provides a serene atmosphere and is a great place to observe local wildlife. The section from Mill Street south to Cross Street forms a greenbelt between residential communities and the Lawrence Preserve nature area, whose wetlands can be further explored through a network of paths extending from the trail. The ravine that forms the trail's route through the Washington College campus and the embankment on the portion north of Morgnec Road are also notable for their beauty and serenity.
My only caveats with this premier small town trail are the busy crossings on Morgnec Road and High Street, though flashing signal lights that warn motorists when trail users are crossing reduce the danger to a degree and the lack of any direct connection to Washington College. It would also be nice if a separate connector path or sidewalk could be built along Morgnec Road that would link the NW Spur of the trail with the main route on the north side of town so that trail users don't have to use the shoulder of that busy road.
Although currently confined to Chestertown, local officials are exploring plans to extend the Wayne Gilchrest Trail further north along the old RR towards Worton, forming part of a bigger network of greenways on the Eastern Shore.
Little change in grade. Easy to get to - parking available at Wilmer Park. Not too busy for a run or bike ride.
Paved, fast trail. Found on off-shoot paved trail that added another mile to the ride. Perfect if you are looking for an easy trail or to get in a quick ride.
Great trail, but difficult to access especially on the northern end because it is so below grade level and the banks are very steep.
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