Dry stone masonry structures (retaining walls, check dams, stone piles) are found throughout Santa Cruz Island. Over 200 of the structures are located on the east end of the island. These features were constructed by Italian stone masons and laborers between 1880 and 1900 for the Justinian Caire family, which owned the island. Although the work was probably carried out by both skilled stone masons and less skilled workers, as differences in quality can be detected in the various structures, the masonry involved has been examined by experts and has been judged as "good quality work, built to high standards."

Retaining walls were constructed for road support and erosion control. The early records of the various ranch foremen describe these projects. The stone retaining wall supporting the road out of Scorpion Valley towards Smugglers Cove is notable for its massive size, number and large size of rocks used to build it, and the difficulty of constructing such a large structure in its steep hillside location. Walls are still visible today along the Scorpion and Smugglers stream beds and along the Cavern Point trail.

Check dams were built in the drainages leading into the developed valleys to slow the force and amount of water entering these valleys and to capture the eroding sediment. Evidence of flooding at Scorpion Ranch has been found as far back as 1916; the dams and retaining walls were an effort to protect the ranch structures from flooding. Some of the best examples of these dams can be seen along the trail to Cavern Point.

Many of the retaining walls and check dams have deteriorated over time from erosion, flooding, and lack of maintenance. In an effort to preserve this slice of history, the National Park Service began repairing these dry stone structures in 1999. Nearly 100 retaining walls and check dams have been repaired during this period.