Originally referred to in John Charles Olmsted’s 1903 report to the Portland Park Commissioners as South Hillside Parkway, this land was proposed as one of the main scenic drives leading south out of the city. The parkway adjoins the River View Cemetery property that was gifted to the city in 1854 by one of Portland’s first permanent white settlers, James Terwilliger. Following Terwilliger’s death in 1892, and the city’s subsequent acquisition of adjoining land, his family deeded a right-of-way through their property in 1909. The deed specified that the land was to be used as a boulevard or parkway for the benefit and use of the public, which helped preserve and protect its wooded character and unobstructed views during several construction stages in subsequent years. The parkway was named in Terwilliger's honor in 1912.
Although the Olmsted Brothers firm had sketched preliminary plans for the roadway development, the final plan was drawn by the superintendent of parks, Emanuel Mische, John Charles Olmsted’s recommendation for the position. The parkway opened in 1912 and was formally dedicated two years later.
The current parkway of about 115 acres winds from downtown along the west hills, passing through the neighborhoods of Marquam Hill, Southwest Hills, and Burlingame, and by Lewis and Clark College before ending at Oregon Route 43 in Lake Oswego. The parkway width includes about 100 feet of land on both sides of the road. It also boasts a parcel donated by Charles and Thelma Norris in 1992, including numerous rhododendrons that Mrs. Norris had planted while a member of the American Rhododendron Society. The Friends of Terwilliger Parkway was established in the early 1990s with a mission to protect the historic, natural, and recreational character of the parkway. In 2021 they were instrumental in listing Terwilliger Parkway in the National Register of Historic Places.