The roadway extends between the New York Botanical Garden (where its southeast end meets the Bronx River Parkway) and Van Cortlandt Park (where its northwest end meets the Henry Hudson Parkway).

The southern end of the parkway was once home to another creek called Schuil Brook, running under what is now Middlebrook Road, which supplied water to a British fort located on old Van Cortlandt Avenue East during the American Revolutionary War.

[5] In the 1870s, landscape architect Frederick Law Olmsted envisioned a greenbelt across the Bronx, consisting of parks and parkways that would align with existing geography.

[8] Around the same time, New York Herald editor John Mullaly pushed for the creation of parks in New York City, particularly lauding the Van Cortlandt and Pell families' properties in the western and eastern Bronx respectively.

[7]: 49 [9] There were objections to the system, which would apparently be too far from Manhattan, in addition to precluding development on the parks' sites.

[7]: 48 The road was reconstructed between 1935 and 1937, including widening the entire parkway, making the section from the Saw Mill to Gun Hill Road, replacing the intersection at Jerome Avenue with an overpass, and installing a wide median between Marion Avenue and the Grand Concourse.