In 1890, the year after Pittsburgh received the land for Schenley Park, a temporary trestle was constructed across the ravine known as Junction Hollow to provide access from Oakland.

Construction of the Schenley Bridge began in July 1896[7] and it was completed in November 1897,[8] though the approaches were not finished.

[9] Contrasting the new bridge with the old, the Pittsburgh Post wrote, "That huge iron arch, curving above the railroad and those heavy stone supports will never tremble beneath the weight of all the people who can pack themselves upon it, even should they be piled layer upon layer.

"[10] Bigelow originally planned to have the old Schenley Bridge moved to the end of Wilmot Street (now Boulevard of the Allies) to provide an entrance to the park from South Oakland;[11] however, the structure was ultimately sold for scrap instead.

The Schenley Bridge and a boiler plant dubbed the Cloud Factory, sited just northeast of the bridge's Oakland abutment, were settings in The Mysteries of Pittsburgh, the 1988 debut novel by the Pulitzer Prize-winning writer Michael Chabon.