The Gwynns Falls Trail follows a valley that has served as both a transportation avenue and an obstacle since the days of American Indians and European colonists. Early roads were privately owned turnpikes that charged tolls; they became public highways with the advent of automobiles. Streetcars, electrified in the 1880s, served commuters until the period after World War II, when buses replaced them. America's first railroad, the Baltimore and Ohio, crossed the valley near Wilkens Avenue. In the early 1900s the Western Maryland Railroad ran tracks through the valley to connect with port facilities on the Middle Branch at Locust Point.
... we gave much thought to ... securing a first-class railroad line, without ... impairing ... the scenery ... along Gwynns Falls.
Olmsted report on Baltimore parks, 1904
A streetcar passes through Gwynn Oak Amusement Park about 1900.
A Frederick Turnpike tollgate was located just west of the Gwynns Falls at Mount Olivet Cemetery in the early 1900s.
This 1932 photograph shows the Western Maryland Railroad along the valley's west bank, the Pennsylvania Railroad Bridge, Western Cemetery, and Ellicott Driveway passing under the railroad bridge.
Western Maryland Railroad workers stand by a steam locomotive in front of grain storage silos at Locust Point.