The Shipley Trail, at SCCF's Bailey Homestead Preserve, opened in March 2014. It connects two City of Sanibel parks:  Roadside City Park on Periwinkle and Pond Apple Park/Trail, which begins at the Chamber of Commerce. The trails are connected by the Starr D. Thomas Memorial Boardwalk, which was built through a partnership between SCCF and the City.

The Shipley Trail crosses old-growth upland areas and passes the windmill on the Bailey Homestead. The trail runs parallel to SCCF's Native Landscapes & Garden Center which is open to the public with demonstration gardens and native plants for sale.