It was designed by Charles Eliot and the Olmsted Brothers to provide a parkway setting that provided access from Brookline, Newton, and the western portions of Boston to the southern parks of the Emerald Necklace.

From its northern end at Beacon Street, it runs for roughly two-thirds of a mile with no intersections while passing through a conservation area consisting of the Hammond Pond Reservation and the Webster Conservation Area.

[4] It crosses the MBTA Green Line D branch, formerly the Highland branch of the Boston and Albany Railroad, along the way, and has at grade intersections for Boston College's Robstein Art Center, The Shops at Chestnut Hill and The Street Chestnut Hill before reaching an interchange with Massachusetts Route 9 at roughly its midpoint.

Farther to the south, the east side of the parkway has a residential area of larger homes with expansive lawns, while the west side is adjacent to the DCR Lost Pond Reservation and the Town of Brookline's Skyline Park.

[3] In 2021, the Department of Conservation and Recreation proposed to redesign the portion of the parkway north of Route 9.