Midpeninsula Regional Open Space District supports the creation of a regional network of trails that connects communities to open space both within the preserves that the agency manages and throughout the district itself. As a result, Midpen engages in partnership projects, including the Saratoga to the Skyline Trail project, as envisioned by the City of Saratoga. Linking the city's Quarry Park with Santa Clara County's Sanborn County Park, the 9.7-mile trail opened to the public in November 2020.
Midpen and the City of Saratoga's partnership began in 2011, when Midpen financially supported the city's purchase of the 64-acre property that became Quarry Park. When planning for the Saratoga-to-the-Skyline Trail project began in 2017, Midpen provided technical support and committed $1.365 million in funding towards engineering design, environmental review and construction.