Located between Taylor Street and Skyport Drive, the site where the two freeways cross has two restrictions that prevent the construction of any connecting ramps.

First, because of its proximity to the runways at San Jose International Airport, any elevated ramps running above the SR 87 mainline would interfere with flight paths.

Second, tunneling underneath would leave a significant environmental impact on the nearby Guadalupe River.

The path diverges from the freeway for 1.1 miles (1.8 km) near Capitol Expressway, running along city streets near the highway.

The path diverges again from the freeway for 0.7 miles (1.1 km) near Curtner Avenue running along city streets near the highway.

From the northern terminus of the upper (southern) segment of the Guadalupe River Trail, go east on Chynoweth Avenue, cross to the north side of street at Pearl Avenue, cross under Highway 87 and enter the Highway 87 Bikeway.

The entrance to the eastern bank trail is on Palm Street, just to the north of West Virginia Avenue.

A Guadalupe Parkway connection between Downtown San Jose and the present day US 101 had existed since the early 1960s; the road channeled traffic between the Bayshore Freeway and ramps that connected directly to Market Street.

However, construction on a freeway over the same path and southward beyond Downtown began a decade later and stretched across 30 years.

Finally, with all grade-level intersections replaced by grade separations, construction of the six-lane freeway between Taylor Street and the Highway 101/North First interchange began in the late 1990s was completed in 2004, and the name Guadalupe Parkway stopped being used (except on some signs).

[11] The right-of-way for SR 87 south of I-280 includes two tracks for the Blue Line of the VTA light rail system.

[2] A resolution of the state legislature in 2007 named a section of this highway (between I-280 and Julian Street/Santa Clara Street) the Lewis E. Platt Memorial Highway (honoring the late chairman, president and chief executive officer of Hewlett-Packard who successful campaigned for local ballots to fund transportation improvements), and required that signage be paid by private donations.